Boontanonda, Pavares’s team published research in Journal of the Chemical Society, Chemical Communications in | CAS: 20117-47-9

Journal of the Chemical Society, Chemical Communications published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, Formula: C5H10O.

Boontanonda, Pavares published the artcilePalladium(II)-catalyzed ring expansion of methylenecyclobutanes and related systems, Formula: C5H10O, the publication is Journal of the Chemical Society, Chemical Communications (1977), 583-4, database is CAplus.

Treatment of methylenecyclobutane (I; R = H) with PdCl2-CuCl2-O2-H2O in C6H6 at 0° gave 75% cyclopentanone (II; R = H). I (R = CH2NHAc, CN) underwent analogous oxidative ring expansion at room temperature and 60° resp. on treatment with PdCl2-CuCl2-O2-H2O in EtOAc to give 65 and 82% II resp., whereas similar treatment of camphene (iso-PrOH, 65°), methylenecamphor (EtOAc, 45°) and methylenecyclopentane (EtOAc, 65°) gave only low yields of the corresponding ring expanded products. Methylenenorbornane (iso-PrOH, 45°), and β-pinene (Me3COH, 45°) gave the corresponding bis-π-allyl palladium chloride dimers quant. on treatment with PdCl23-CuCl2-O2-H2O whereas similar treatment of 4-RC6H4CPh:CH2 (R = H, MeO) gave 28.5% Ph2CO and 28.5% PhCH2COPh, and 62.5% PhCOC6H4OMe-4, resp.

Journal of the Chemical Society, Chemical Communications published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, Formula: C5H10O.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Vinogradov, M. G.’s team published research in Izvestiya Akademii Nauk, Seriya Khimicheskaya in | CAS: 20117-47-9

Izvestiya Akademii Nauk, Seriya Khimicheskaya published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C14H10N2O, Synthetic Route of 20117-47-9.

Vinogradov, M. G. published the artcileSelective method of 5-chloro-2-pentanone preparation, Synthetic Route of 20117-47-9, the publication is Izvestiya Akademii Nauk, Seriya Khimicheskaya (1995), 774-6, database is CAplus.

5-Chloro-2-pentanone (1) was prepared by reaction of 1-methylcyclobutanol (3) with Ca(OCl)2, followed by decomposition of the 1-methylcyclobutyl hypochlorite in the presence of a FeII salt. The selectivity of 1 formation from 3 was 98%, and the conversion of 3 was 35-40%.

Izvestiya Akademii Nauk, Seriya Khimicheskaya published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C14H10N2O, Synthetic Route of 20117-47-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Finkel’shtein, E. Sh.’s team published research in Neftekhimiya in 25 | CAS: 20117-47-9

Neftekhimiya published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, HPLC of Formula: 20117-47-9.

Finkel’shtein, E. Sh. published the artcileElectrophilic addition to methylenecyclobutane and bicyclobutylidene, HPLC of Formula: 20117-47-9, the publication is Neftekhimiya (1985), 25(1), 48-57, database is CAplus.

Title reaction of methylenecyclobutane (I) with ROH (R = Me, Et, Bu, 1-methylcyclobutyl, Ph, Ac, ClCH2CO, FCH2CO, CCl3CO, CF3CO) in the presence or absence of hexane or cyclohexane and/or 80% H2SO4 gave the corresponding ethers and esters II. PhOH gave 4-R1C6H4OH (R1 = 1-methylcyclobutyl) and 2,4,6-R13C6H2OH (same R1) as the major products. Analogous reactions of bicyclobutylidene with ROH (R = H, Me, Ac, CF3CO, Ph) gave bicyclo[3.3.0]octanes III (R2 = OH, OMe, OAc, O2CCF3, C6H4OH-4, resp.). I reacted with aqueous HCHO under these conditions to give 5,7-dioxaspiro[3.5]nonane, methanolysis which gave diol IV (R = H) (V) and IV (R = Me). Dehydrating V gave 1-vinylcyclobutene . The NMR and mass spectra of the products were interpreted.

Neftekhimiya published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, HPLC of Formula: 20117-47-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Alder, Kurt’s team published research in Chemische Berichte in 85 | CAS: 20117-47-9

Chemische Berichte published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, Safety of 1-Methylcyclobutan-1-ol.

Alder, Kurt published the artcileSubstituting additions. IX. Substituting addition and diene synthesis with methylenecyclobutane, Safety of 1-Methylcyclobutan-1-ol, the publication is Chemische Berichte (1952), 556-65, database is CAplus.

cf. C.A. 44, 2927i. The substituting addition of maleic anhydride (I) to methylenecyclobutane (II), which is similar to the addition of I to methylenecyclohexane and -pentane, is studied. Heating an intimate mixture of 400 g. pentaerythrityl tetrabromide and 410 g. Zn dust in 600 cc. H2O slowly to 85° with stirring and adding over a period of 2 hrs. 300 cc. MeOH in small portions give 70-85% II, b. 41-2°. Heating 25 cc. II and 50 g. I in 50 cc. dry C6H6 in a bomb tube 30 hrs. at 190-5°, washing the reaction product with Me2CO into a beaker, and allowing the solvent to evaporate cause the crystallization of 35% adduct (III), consisting of 1 mol. II and 2 mols. I, m. 170-1°, which, on standing in the open air, changes to a tetracarboxylic acid (IV), m. 165-6°. On catalytic hydrogenation of 1 g. IV in AcOEt with PtO2, the saturated tetracarboxylic acid, m. 193°, is formed. Heating 1.5 g. III and 1.4 g. S 2.5 hrs. at 240-5°, dissolving the reaction products in Na2CO3, oxidizing with KMnO4, destroying the excess KMnO4 with NaHSO3, washing with ether, acidifying, evaporating the filtered solution in vacuo to dryness, and extracting the residue with hot Me2CO give a tetracarboxylic acid (V) of Va as an oil. Oxidation of V with concentrated HNO3 on a water bath and, finally, in a bomb tube at 165° gives trimellitic acid (VI), m. 221°, which, heated above its m.p. and sublimed, gives the anhydride, m. 161°. Distilling the residue of the mother liquor of III in vacuo gives 3 g. of a fraction, b13 155-60°, which, dissolved in Na2CO3, filtered, acidified, and extracted with ether, gives the dicarboxylic acid (VII), of VIIa, an adduct of 1 mol. isoprene and 1 mol. I, m. 155°. When hydrogenated in AcOEt in the presence of PtO2, VII gives 4-methylcyclohexane-1,2-dicarboxylic acid, m. 165°. Heating 1 g. VII with 0.35 g. S 2.5 hrs. at 230-5° and then heating the reaction product with concentrated HNO3, finally 6 hrs. in a bomb tube at 160°, give VI. The formation of VII is the result of a rearrangement of II via CH2.CH2.CH:CMe to CH2:CHCMe:CH2. Heating 20 cc. II and 35 cc. freshly distilled CH2:CHCO2H in 40 cc. dry C6H6 30 hrs. at 200° and fractionally distilling in vacuo the reaction product from 2 runs give 45% distillate (VIII), b13 120-45°. Shaking VIII with ether and dilute KOH, acidifying the alk. solution with HCl, and extracting with ether give 18 g. of an acid mixture which, redistilled, b13 130-8°. It is separated into 7.2 g. crystalline 4-methyl-Δ3-tetrahydrobenzoic acid (IX), m. 100° (anilide, prepared via its Me ester, long needles, m. 154°; hydrazide, long silky nedles, m. 151-2°), and 7.9 g. of an oily adduct (X), CH2.CMe:CH.CH2.CH2.CHCO2H. Hydrogenating IX with PtO2 in AcOEt and treating the Me ester, prepared with CH2N2, with PhNH2 give the anilide of the saturated acid, C14H19ON, long needles, m. 130-1°. Ozonization of 2.5 g. IX in 100 cc. AcOEt with O containing 3-4% O3 and reduction of the reaction product with PtO2 and a few drops MeOH give MeCOCH2CH2CH(CO2H)CH2CO2H, hard crystals, m. 122-3° (semicarbazone, m. 178°). Heating 1 g. IX with 4 cc. concentrated H2SO4 15 min. on a boiling water bath and pouring the mixture on ice give p-MeC6H4CO2H, m. 178°, in good yield. Heating 1.4 g. IX 2.5 hrs. at 230-5° with 0.64 g. S, dissolving the reaction product in Na2CO3, treating it with KMnO4, decolorizing with NaHSO3, and acidifying give p-C6H4(CO2H)2 (di-Me ester, m. 140°). Heating 1.4 g. X 2.5 hrs. at 230-5° with 0.64 g. S gives m-MeC6H4CO2H, m. 110°, which, oxidized with KMnO4, gives m-C6H4(CO2H)2 (di-Me ester m. 68°). Distillation of the residue of the washed ether solution obtained in the working up of VIII gives 10 g. 1-hydroxy-1-methylcyclobutane (XI) acrylate (XII), b13 125°, which (8 g.), refluxed 6 hrs. with concentrated KOH-MeOH, gives XI, b. 117-20° (phenylurethan m. 139°). Ozonization of XII gives HCHO. Acidification of the alk. solution gives 1.5 g. IX. Heating 20 cc. II and 20 cc. AcOH 48 hrs. at 200°, diluting the mixture with H2O, and distilling the washed (dilute Na2CO3, H2O) oil give 9 g. of a mixture, b. 140-200°. Saponification with KOH-MeOH of the fraction, b. 130-60°, gives XI. Refluxing 4 g. of the fraction, b. 170-85°, 4 hrs. with 2 g. I in a little ether, distilling off the ether and unreacted reagents, and dissolving the residue in hot concentrated Na2CO2H give the Na salt of an adduct of I with α-terpinene, as fatty shiny scales. Heating the free acid above its m.p. gives the anhydride, m. 62-3°.

Chemische Berichte published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, Safety of 1-Methylcyclobutan-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Dem’yanov, I. N.’s team published research in Zhurnal Russkago Fiziko-Khimicheskago Obshchestva in 45 | CAS: 20117-47-9

Zhurnal Russkago Fiziko-Khimicheskago Obshchestva published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, Category: alcohols-buliding-blocks.

Dem’yanov, I. N. published the artcileVinyltrimethylene and its Derivatives, Category: alcohols-buliding-blocks, the publication is Zhurnal Russkago Fiziko-Khimicheskago Obshchestva (1913), 176-84, database is CAplus.

The alc. (a) obtained by shaking vinyltrimethylene (b) with H2SO4 (Gustavson, J. prakt. Chem., [2] 54, 104), not being oxidizable to an aldehyde or ketone, is doubtless tertiary; it b755, 117.5-8.5° m. -5°, d422 0.889, n422 1.4315. Of the 2 formulas of (a), and preference is given to the 2nd. By converting (a) into an iodide (b22 50°) and treating the latter with Zn + AcOH a mixture of a hydrocarbon C5H10 (c) and the acetate of (a) was obtained. (c) b753 34-5°, d00 0.6973, d40 0.6805, nD17 1.3814; its formula is supposed to be. A hydrocarbon almost identical with (c) is more readily obtainable by reducing (b) with H + Pt black. The acetate of (c) b. 130-2.5°, d420 0.9351, nD20 1.419.

Zhurnal Russkago Fiziko-Khimicheskago Obshchestva published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, Category: alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Gu, Yu-Rui’s team published research in Organic Letters in 21 | CAS: 20117-47-9

Organic Letters published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, HPLC of Formula: 20117-47-9.

Gu, Yu-Rui published the artcileIminyl Radical-Triggered Intermolecular Distal C(sp3)-H Heteroarylation via 1,5-Hydrogen-Atom Transfer (HAT) Cascade, HPLC of Formula: 20117-47-9, the publication is Organic Letters (2019), 21(4), 917-920, database is CAplus and MEDLINE.

An efficient iron-catalyzed intermol. remote C(sp3)-H heteroarylation of alkyl ketones has been developed via an iminyl radical-triggered 1,5-hydrogen-atom transfer (HAT) cascade. This protocol was amenable to a wide variety of alkyl ketones and heteroaryls, thus providing a straightforward method for the late-stage functionalization of alkylketones and heteroaryls to obtain, e.g., I.

Organic Letters published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, HPLC of Formula: 20117-47-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Tomer, K. B.’s team published research in Tetrahedron in 29 | CAS: 20117-47-9

Tetrahedron published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C4H8F3NO, Synthetic Route of 20117-47-9.

Tomer, K. B. published the artcileMass spectrometry in structural and stereochemical problems. CCXXXI. Differentiation between tautomeric ion structures (phenol versus cyclohexadienone), Synthetic Route of 20117-47-9, the publication is Tetrahedron (1973), 29(22), 3491-6, database is CAplus.

Ion cyclotron resonance and pulsed double resonance spectra of ion-mol. reactions of bicyclo[2.2.2]oct-2-en-5,7-dione, PhOD, and C6D5OH with Pr2CO and 1-methylcyclobutanol were determined and the results applied to the structure determination of the C6H6O+ ion generated by electron impact induced expulsion of CH2:CO from PhOAc. The ion was PhO+, not cyclohexadienone+.

Tetrahedron published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C4H8F3NO, Synthetic Route of 20117-47-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Sengupta, Debasis’s team published research in Journal of Photochemistry and Photobiology, A: Chemistry in 75 | CAS: 20117-47-9

Journal of Photochemistry and Photobiology, A: Chemistry published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C16H25BO2, Safety of 1-Methylcyclobutan-1-ol.

Sengupta, Debasis published the artcileStudies on the Norrish type II reactions of aliphatic α-diketones and the accompanying cyclization and disproportionation of 1 : 4 biradicals, Safety of 1-Methylcyclobutan-1-ol, the publication is Journal of Photochemistry and Photobiology, A: Chemistry (1993), 75(2), 151-62, database is CAplus.

The Norrish type II process of several alkyl diketones was examined using the AM1 semi-empirical MO method with complete geometry optimization at the CI level in the RHF frame. UHF calculations of the triplet state of the diketone lead to a decrease in symmetry and strong localization of excitation on one carbonyl. The results of RHF+CI reveal that diketones have much lower reactivities than monoketones and the barriers to conformational change in diketones play an important role in the triplet reaction. The cyclization and disproportionation reactions of the resulting 1:4 biradicals were studied in the UHF frame and the results were compared with those derived from alkyl monoketones. In many respects, the reactions of 1:4 biradicals derived from alkyl monoketones parallel those derived from diketones. The free valence indexes on the radical sites correlate qual. with the radical-like reactivities.

Journal of Photochemistry and Photobiology, A: Chemistry published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C16H25BO2, Safety of 1-Methylcyclobutan-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Cox, Eugene F.’s team published research in Journal of the American Chemical Society in 83 | CAS: 20117-47-9

Journal of the American Chemical Society published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, Name: 1-Methylcyclobutan-1-ol.

Cox, Eugene F. published the artcileSmall-ring compounds. XXXIV. Carbonium ion reactions of 1-methylcyclobutyl-, (1-methylcyclopropyl)carbinyl, and (β-methylallyl)carbinyl derivatives, Name: 1-Methylcyclobutan-1-ol, the publication is Journal of the American Chemical Society (1961), 2719-24, database is CAplus.

cf. CA 46, 1453a, 55, 22160d. (1-Methylcyclopropyl)carbinyl chloride (I) solvolyzed in 50% aqueous EtOH about 10 times faster than 1-methylcyclobutyl chloride (II) and as fast as Me3CCl. Treatment of (1-methylcyclopropyl)carbinylamine (III) and 1-methylcyclobutylamine (IV) with HNO2 gave only 1-methylcyclobutanol (V). CH2:CMeCH2CH2NH2 (VI) gave V as the only cyclic product. About 3% of the C14 content of V from the deamination of III-α-C14 (VII) was found at the 3-position. These results were interpretable in terms of classical carbonium ions and(or) substituted bicyclobutonium ion intermediates with fairly localized pos. charges. CH2: CMeCO2Me added to CH2N2-Et2O at 0°, the resulting pyrazoline (90%) pyrolyzed in small quantities, and the combined crude product distilled yielded 316 g. crude Me ester (VIII) of 1-methylcyclopropanecarboxylic acid (IX), containing some unsaturated material, which treated in petr. ether with slightly alk. 0.25M KMnO4 at 0° and worked up gave pure VIII, b60.4-65.6 55.9-7.1°, n25D 1.4192-1.4193. The VIII hydrolyzed gave 90% IX, m. 32.4-4.3° (all m.ps. corrected); p-bromophenacyl ester m. 64.1-5.0° (50% aqueous EtOH); anilide m. 100.5-1.6° (50% aqueous EtOH), 100.6-1.3° (hexane). The Ag salt of IX in Freon-12 treated with Br gave 71% 1-methylcyclopropyl bromide (X), b740 77.2-8.0°, n25D 1.44711.4474. A small amount of X converted to the Grignard reagent and treated with PhNCO gave 1-methylcyclopropanecarboxanilide, m. 99.2-100.1°. IX was converted into 72% amide, m. 145.7-6.9°. CH2:CMeCN with CH2N2 in Et2O yielded 1-methylcyclopropanecarbonitrile (XI), b765 127.7-8.5°, n25D 1.4128. VIII reduced with LiAlH4 gave (1-methylcyclopropyl)carbinol, b739 125.8-6.3°, n25D 1.42901.4292; 3,5-dinitrobenzoate m. 88.9-90.7° (C6H6-cyclohexane). XI reduced with Na-EtOH gave 56% III, b764 95.0-6.8°, n25D 1.4269. XI reduced with LiAlH4 in Et2O gave 70% III, b761 94.3-6.1°, n25D 1.4207-1.4273; N-phenyl-N’-(1-methylcyclopropylcarbinyl)thiourea m. 112.7-13.5° (95% EtOH). Me2C(CH2OH)2 treated with PBr3 and the dibromide cyclized gave 1,1-dimethylcyclopropane (XII), b738 19.0-20.0°. XII (74.5 g.) chlorinated by the method of Robert and Mazur (loc. cit.) gave 102 g. mixture of 49% I, 16% II, 14% CH2: CHMeCH2Cl, and 32% unreactive chloride, which carefully refractionated gave pure I, b735, 83.0-3.9°, n25D 1.4045-1.4052. The H2SO4-catalyzed addition of H2O to methylenecyclobutane (XIII), b739 41.0-2.0°, yielded 68% V, b746 117.8-18.3°, n25D 1.4332-1.4336. The hydrolysis of II yielded 40% V, b756 117.1-18.9°, n25D 1.4329. Cyclobutanone with MeMgBr gave 67% V, b765 118.3°, n25D 1.4332. HCl added to XIII yielded 81% II, b742 90.8-1.3°, n25D 1.4283-1.4287. MeCN (9.0 g.), 100 cc. glacial AcOH, and 20 cc. concentrated H2SO4 treated with stirring with 13.6 g. XIII, stirred 1 hr. at 20°, cooled, diluted with 300 cc. H2O, basified with Na2CO3, and extracted with Et2O, and the extract worked up yielded 17.7 g. N-(1-methylcyclobutyl)acetamide (XIV). XIV (10.0 g.) and 400 cc. 4N KOH in (CH2OH)2 refluxed 48 hrs. and continuously extracted with Et2O yielded 3.1 g. IV, b764 85.5-6.0°, n25D 1.4200. XIII (13.6 g.), 11.0 g. 90% NaCN, and 25 cc. glacial AcOH treated at 0° with 25 cc. AcOH and 50 g. concentrated H2SO4 during 25 min., stirred 3 hrs. at 0°, 1 hr. at room temperature, and 45 min. at 55°, kept overnight at room temperature, treated slowly with stirring with 120 g. NaOH in 250 cc. H2O, refluxed 8 hrs., and steam distilled, and the distillate (250 cc.) extracted 18 hrs. with Et2O yielded 8.03 g. IV, b745 84.0-4.7°, n25D 1.4292-1.4293; N-phenyl-N’-(1-methylcyclobutyl)thiourea, m. 135.3-5.8° (aqueous EtOH). CH2:CMeCH2CH2Cl was converted by the method of Kharasch and Fuchs (CA 38, 62819) in 35% yield to CH2:CMeCH2CH2OH (XV), b741 127.9-30.4°, n25D 1.43051.4312; 1-naphthylurethan m. 66.7-7.3° (petr. ether). XV (8.61 g.), 25 cc. dry Et2O, 18.5 g. Bu3N treated with stirring at 0° with 11.9 g. SOCl2 during 3 hrs. gave CH2:CMeCH2CH2Cl (XVI), b739, 101.0-2.7°, n25D 1.4301-4305. XVI with K phthalimide in HCONMe2 yielded 85% N-I-(3-methyl-3-butenyl)phthalimide (XVII), m. 51.2-2.8°. Hydrazinolysis of XVII in HClO4 gave 26% VI, b101 47.6-8.5°, n25D 1.4288. CH2:CMeCHO with MeMgBr yielded CH2:CMeCH(OH)Me, b59.9-60.4 54.6-6.8°, n25D 1.4241-1.4242. 3-Methyl-3-carbomethoxy-l-pyrazoline pyrolyzed and the high-boiling fractions of the product redistilled gave Me tiglate, b740 136.9-7.1°, n25D 1.4338, which reduced with LiAlH4 yielded about 40% MeCH:CMeCH2OH, b. 137.6-7.9°, n25D 1.4386-1.4401. III (12.8 g.) in 50 cc. H2O and 180 cc. 1.0N HClO4 treated during 0.5 hr. with stirring with 30 g. NaNO2 in 100 cc. H2O, heated 1 hr. at 50-65 mm., and steam-distilled, the aqueous phase of the distillate saturated with K2CO3 and extracted with Et2O, and the combined organic layer and extract distilled gave 0.72 g. V. The Grignard reagent from X carbonated in vacuo with C14O2, diluted with inactive IX, and distilled gave IX-α-C14, b19.2-19.4 96.6-7.4° (radioactive yield 88%), which was converted to the amide and further by reduction with LiAlH4 to 51% VII. VII treated in AcOH with NaNO2 in portions, poured into 20% aqueous NaOH, and extracted with Et2O, and the resulting mixture of labeled alc. and acetate reduced with LiAlH4 gave V. VII.HCl oxidized with alk. KMnO4 and a portion of the resulting acid converted to the amide gave a material containing 0.128 microcuries/millimole; another portion of the acid was subjected to a Schmidt degradation and the resulting amine converted to the benzamide, m. 161.7-3.0°, containing 0.000-37 microcuries/millimoles, corresponding to 0.29% of the original activity. The rates of the solvolysis in 50% EtOH were determined for the following compds (reaction temperature, and k1 × 105/sec. given): cyclopropyl bromide, 130°, 0.26; X, 130°, 10.5; II, 50°, 61.7; II, 30°, 7.15; I, 30°, 69; XVI, 90°, 0.17.

Journal of the American Chemical Society published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, Name: 1-Methylcyclobutan-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Brown, Pamela’s team published research in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in | CAS: 20117-47-9

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, Safety of 1-Methylcyclobutan-1-ol.

Brown, Pamela published the artcileβ-Lactamase-stable penicillins. Synthesis and structure-activity relationships of (Z)-alkyloxyimino penicillins; selection of BRL 44154, Safety of 1-Methylcyclobutan-1-ol, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1991), 881-91, database is CAplus.

A series of (Z)-2-alkyloxyimino-2-(2-aminothiazol-4-yl)acetamidopenicillins I (R = Me, Et, CHMe2, CMe3, cycloalkyl) were prepared New methodol. was developed to prepare tertiary alkyl oximes. High stability to β-lactamases and potent antibacterial activity have been achieved against Gram-pos. and certain Gram-neg. organisms. Activity against methicillin-resistant Staphylococcus aureus was an unexpected finding. BRL 44154 (I; R = cyclopentyl) has been selected for further study.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, Safety of 1-Methylcyclobutan-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts