Category: 83706-94-9

Gao, Pan published the artcileCopper-Catalyzed Asymmetric Defluoroborylation of 1-(Trifluoromethyl)Alkenes, Application In Synthesis of 83706-94-9, the publication is Chem (2018), 4(9), 2201-2211, database is CAplus.

Gem-Difluoroalkenes have steric and electronic profiles similar to those of ketones, aldehydes, and esters, and consequently have been used widely as carbonyl isosteres in modern drug discovery. Although many attempts have been made to achieve gem-difluoroalkenes, the induction of enantioselectivity at the α position of a gem-difluorovinyl group still remains a challenge. Herein, an efficient method for the construction of gem-difluoroallylboronates with high enantiomeric excess via a copper-catalyzed defluoroborylation of 1-(trifluoromethyl)alkenes with B₂pin₂ is described. The reaction conditions were mild, and a variety of common functional groups, such as ether, fluoride, chloride, bromide, iodide, ester, cyano, sulfide, amino, and indoyl groups, were well tolerated. Furthermore, we not only applied this developed system as a powerful synthetic tool for the late-stage modification of complex compounds but also highlighted the utility of the formed compounds in synthesis.

Chem published new progress about 83706-94-9. 83706-94-9 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is (E)-4,4,4-Trifluorobut-2-en-1-ol, and the molecular formula is C4H5F3O, Application In Synthesis of 83706-94-9.

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

Wang, Bing-Lin published the artcileSynthesis of trifluoromethylated analogues of α-L-fucofuranose and α-L-4,6-dideoxyxylohexopyranose, Formula: C4H5F3O, the publication is Journal of Fluorine Chemistry (2006), 127(4-5), 580-587, database is CAplus.

Efficient strategy to trifluoromethylated trans-disubstituted alkene I was developed starting from com. available 4,4,4-trifluoro-3-oxo-butyric acid Et ester. 6-Deoxy-6,6,6-trifluorosugars II and III were synthesized from I in high stereoselectivity and in a straightforward fashion. The key steps were Sharpless asym. dihydroxylation, regioselective ring opening of trifluoromethylated cyclic sulfate, Horner-Wadsworth-Emmons reaction, oxidation and intramol. heterocyclization. It was noteworthy that the oxidation of alcs. followed by deprotection and acetylation gave the single isomer target mols. II and III, resp.

Journal of Fluorine Chemistry published new progress about 83706-94-9. 83706-94-9 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is (E)-4,4,4-Trifluorobut-2-en-1-ol, and the molecular formula is C7H10N2O2, Formula: C4H5F3O.

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

Pegolotti, J. A. published the artcileAllylic rearrangements. L. Reactions of α- and γ-trifluoromethylallyl alcohols with thionyl chloride and thermal decomposition of the chlorosulfinate intermediates, Synthetic Route of 83706-94-9, the publication is Journal of the American Chemical Society (1961), 3251-8, database is CAplus.

The reactions of α-(trifluoromethyl)allyl alc. (I) and γ-(trifluoromethyl)allyl alc. (II) with SOCl₂ in Et₂O and SOCl₂ were investigated. In the absence of amines, I in either solvent yielded α-(trifluoromethyl)allyl chlorosulfinate (III) only. With I, Bu₃N, and SOCl₂ (equimolar in ether) the products were 68% III and 32% γ-(trifluoromethyl)allyl chloride (IV) after 1 hr. The presence of Bu₃NHCl in the mixture gave small amounts of IV. II and SOCl₂ in ether yielded γ-(trifluoromethyl)allyl chlorosulfinate (V), which slowly gave IV on standing. In the presence of Bu₃N, II and SOCl₂ gave IV exclusively. III and V, the first isolable allylic chlorosulfinates outside of allyl chlorosulfinate itself, were thermally decomposed with no solvent and in n-decane and nitrobenzene and the rates of decomposition measured by the rate of evolution of SO₂ [compound, solvent, decompn, temperature, and rate (10⁵k. sec.^-1, extrapolated to 100°) given]: III, none (3 runs), 108-110° (103°, 105-106°), 6.5 (6.2, 7.3); III, nitrobenzene, 106-108°, 10.0; III, n-decane, 124°, 1.5; V, none (2 runs), 105° (139-142°), 126 (0.27); V, nitrobenzene (2 runs), 115-116° (118-120°), 5.1 (8.8). The insensitivity of the decomposition to solvent was explained in terms of a concerted reaction with predominant covalent character maintained in the intermediate through the rearrangement sequence. II was prepared by the procedure of McBee (CA 49, 10171b). I was prepared by addition of CF₃CHO to the Grignard reagent from vinyl bromide and Mg in tetrahydrofuran; I formed an azeotrope, b. 102-3°, with the solvent. Chromatography of the azeotrope gave I, b. 91.5°, n²⁵_D 1.3450. The α-napthylurethan of I m. 121-3°. Adding 8.9 g. SOCl₂ to 9.4 g. II and 13.9 g. Bu₃N over 30 min. at 0°, stirring 1 hr., then flash distilling gave IV, b. 82.5-83°, n²⁵_D 1.3610. γ-(Trifluoromethyl)allyl n-amyl sulfite (VI) was prepared by adding dropwise over 30 min. a mixture of 3.0 g. II and 1.9 g. anhydrous pyridine to a cooled (-20 to -30°) solution of 5.12 g. n-amyl chlorosulfinate in ether. H₂O was added after 45 min., the layers separated, the ether layer washed, dried, and distilled to yield 2.05 g. VI, b₄ 100-102°, n²⁵_D 1.4099. α-(Trifluoromethyl)allyl n-amyl sulfite (VII) was prepared similarly, b₅ 80-2°, n²⁵_D 1.4030. Addition of 4.86 g. SOCl₂ in ether to a stirred solution of 3.57 g. II in 60 ml. ether at 0° and distillation gave 1.23 g. V, b₆ 55°, n²⁵_D 1.4089. Reaction of V with n-amyl alc. gave VI. Addition of 3.1 g. I to 14.3 g. SOCl₂ and 5.3 g. Bu₃N over 45 min. at 0°, with stirring continued 1 hr., and distillation gave 2.78 g. III, b₃₉ 52°, n²⁵_D 1.4088. Reaction of III with n-amyl alc. gave VII. The refractive indexes of III and V did not change during 5 min. in the refractometer.

Journal of the American Chemical Society published new progress about 83706-94-9. 83706-94-9 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is (E)-4,4,4-Trifluorobut-2-en-1-ol, and the molecular formula is C4H5F3O, Synthetic Route of 83706-94-9.

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

Guo, Rui published the artcileBarbier-type anti-Diastereo- and Enantioselective Synthesis of β-Trimethylsilyl, Fluorinated Methyl, Phenylthio Homoallylic Alcohols, Recommanded Product: (E)-4,4,4-Trifluorobut-2-en-1-ol, the publication is Scientific Reports (2017), 7(1), 1-12, database is CAplus and MEDLINE.

Catalytic Asym. allylation of aldehydes with functionalized allylic reagents represents an important process in synthetic organic chem. because the resulting chiral homoallylic alcs. are valuable building blocks in diverse research fields. Despite the obvious advantages of allyl halides as allylation reagent under Barbier-type conditions, catalytic asym. version using functionalized allyl halides remains largely underdeveloped. Here, authors addressed this issue by employing a chromium-catalysis system. The use of readily available allyl bromides with γ substitutions including trimethylsilyl, fluorinated Me and phenylthio groups provided an efficient and convenient method to introduce those privileged functionalities into homoallylic alcs. Good yields, high anti-diastereo- and excellent enantioselectivities were achieved under mild reaction conditions.

Scientific Reports published new progress about 83706-94-9. 83706-94-9 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is (E)-4,4,4-Trifluorobut-2-en-1-ol, and the molecular formula is C4H5F3O, Recommanded Product: (E)-4,4,4-Trifluorobut-2-en-1-ol.

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

Spielmann, Kim published the artcileDirect Conversion of Primary Alcohols to 1,2-Amino Alcohols: Enantioselective Iridium-Catalyzed Carbonyl Reductive Coupling of Phthalimido-Allene via Hydrogen Auto-Transfer, HPLC of Formula: 83706-94-9, the publication is Journal of the American Chemical Society (2019), 141(36), 14136-14141, database is CAplus and MEDLINE.

The first catalytic enantioselective carbonyl (α-amino)allylations are described. Phthalimido-allene and primary alcs. engage in hydrogen auto-transfer-mediated carbonyl reductive coupling by way of (α-amino)allyliridium-aldehyde pairs to form vicinal amino alcs. with high levels of regio-, anti-diastereo-, and enantioselectivity. Reaction progress kinetic anal. and isotopic labeling studies corroborate a catalytic cycle involving turnover-limiting alc. dehydrogenation followed by rapid allene hydrometalation.

Journal of the American Chemical Society published new progress about 83706-94-9. 83706-94-9 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is (E)-4,4,4-Trifluorobut-2-en-1-ol, and the molecular formula is C7H13NO2, HPLC of Formula: 83706-94-9.

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

Wang, Lei published the artcileCobalt-Catalyzed Diastereo- and Enantioselective Reductive Allyl Additions to Aldehydes with Allylic Alcohol Derivatives via Allyl Radical Intermediates, Recommanded Product: (E)-4,4,4-Trifluorobut-2-en-1-ol, the publication is Journal of the American Chemical Society (2021), 143(32), 12755-12765, database is CAplus and MEDLINE.

Herein an unprecedented cobalt-catalyzed highly site-, diastereo- and enantioselective protocol for stereoselective formation of nucleophilic allyl-Co(II) complexes followed by addition to aldehydes RCHO (R = Ph, 2-furyl, cyclohexyl, etc.) is presented. The reaction features diastereo- and enantioconvergent conversion of easily accessible allylic alc. derivatives, e.g., 2-(3,4-dihydro-1(2H)-naphthalenylidene)ethanol to diversified enantioenriched homoallylic alcs. e.g., I with remarkably broad scope of allyl groups that can be introduced. Mechanistic studies indicated that allyl radical intermediates were involved in this process. These new discoveries establish a new strategy for development of enantioselective transformations through capture of radicals by chiral Co complexes, pushing forward the frontier of Co complexes for enantioselective catalysis.

Journal of the American Chemical Society published new progress about 83706-94-9. 83706-94-9 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is (E)-4,4,4-Trifluorobut-2-en-1-ol, and the molecular formula is C10H10O3, Recommanded Product: (E)-4,4,4-Trifluorobut-2-en-1-ol.

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

McBee, E. T. published the artcileThe preparation and properties of some compounds containing the 4,4,4-trifluorocrotyl group, COA of Formula: C4H5F3O, the publication is Journal of the American Chemical Society (1954), 3725-8, database is CAplus.

The preparation and reactions of several compounds containing the CF₃CH:CHCH₂ group are described, and an unusual reaction of LiAlH₄, the reduction of CF₃CHBrCHBrCO₂Et (I) to CF₃CH:CHCH₂OH (II) at about -80°, is reported. CF₃CH:CHCO₂Et (IIa) (76 g.) in 150 cc. CCl₄ refluxed, the mixture treated dropwise with 90 g. Br with the occasional addition of 150 cc. CCl₄ in portions to keep the Br in solution, the mixture refluxed 24 hrs. while illuminating with a 100-watt bulb, the excess Br and CCl₄ distilled off at atm. pressure, the residue distilled, b₁₅ 65-92°, and the distillate rectified yielded 125 g. (84.5%) I, b₁₅ 90.0-2.0°, n²⁰_D 1.4448, d₂₅ 1.823. I treated with PhCH₂NH₂ (III) gave only III. HBr, m. 220°. CF₃CH:CHCO₂H (IV) (20 g.) and 60 g. BzCl slowly heated to 195° while distilling the acid chloride from the mixture, and the distillate, b. 64-72°, rectified gave 11.5 g. (50%) CF₃CH:CHCOCl (V), m. 77.0-7.5°, n²⁰_D 1.3703, d₂₅ 1.362; it gave with MeNH₂ the N-Me amide of IV, m. 110°. BzCl (300 g.)treated with IV at 150-60° (obtained as the residue from the acidolysis of 100 g. IIa with HCO₂H) dropwise while slowly distilling the acid chloride from the reactor, the residual mixture treated with 100 g. BzCl and heated until no more chloride distilled, and the crude distillate rectified yielded 65.0 g. (67%) V. CF₃CH(OH)CH₂CO₂Et (46.5 g.) in an equal volume Et₂O added dropwise with cooling during 0.5 hr. to 12.0 g. LiAlH₄ in 200 cc. dry Et₂O, the mixture stirred 12 hrs. at room temperature, the excess hydride destroyed with 95% EtOH, the mixture treated with 50 cc. concentrated H₂SO₄ and 250 g. ice, the acid layer extracted twice with 100-cc. portions Et₂O, the combined organic layer and extract distilled, and the residue dried azeotropically with C₆H₆ and distilled yielded 30 g. (83%) CF₃CH(OH)CH₂CH₂OH, b₂₀ 104-5°, viscous cloudy liquid which solidified during several hrs. at 0° to give a white, crystalline and deliquescent solid. I (163 g.) in 200 cc. Et₂O added dropwise with stirring at about -80° to 20 g. LiAlH₄ in 400 cc. dry Et₂O, the mixture stirred 20 hrs. at about -80°, the excess hydride destroyed with 95% EtOH, the reaction complex poured into 100 cc. concentrated H₂SO₄ and 1 kg. ice, the acid layer washed with two 100-cc. portions Et₂O, the combined organic layer and extract dried with Drierite and evaporated, the residue dried azeotropically with 25 cc. C₆H₆ and distilled, and the distillate, b₂₈ 35-54° rectified yielded 33.0 g. (50%) II, b. 128.0-8.5°, n²⁰_D 1.3578, d₂₅ 1.256; phenylurethan, m. 63.0°. B(OMe)₃ (73.0 g.) added dropwise to 18.0 g. NaH in 750 cc. dry, refluxing tetrahydrofuran, the mixture refluxed 2 hrs., cooled, let settle, and filtered under N pressure through glass wool, the filtrate treated with 52.0 g. V in 150 cc. dry tetrahydrofuran, the mixture stirred 2 hrs., treated cautiously with H₂O, and poured into 50 cc. concentrated H₂SO₄ and 1 kg. ice, the resulting homogeneous solution extracted with about 1500 cc. Et₂O in portions, the extract dried with Na₂SO₄, the solvents distilled off, and the residue rectified yielded 12.0 g. (33%) II. IIa (33.5 g.) in an equal volume Et₂O added with cooling during 1 hr. to iso-PrMgBr from 74 g. iso-PrBr and 14.4 g. Mg, the mixture hydrolyzed with ice-cold 10% aqueous H₂SO₄, and the product rectified yielded 17.0 g. (40%) Me₂CHCH(CF₃)CH₂CO₂Et, b₆₅ 98.0-9.0°, n²⁰_D 1.3850, d²⁵ 1.113; Me₂CHCH(CF₃)CH₂CO₂NHNH₂, m. 41.0°; apparently this is the m.p. of a hydrate; after drying in an Abderhalden pistol over P₂O₅ the material turned liquid in air, then solidified to the 41.0° material; Me₂CHCH(CF₃)CH₂CONHPh, m. 129.0°. IIa (33.5 g.) added to EtMgI from 93 g. EtI and 14.4 g. Mg, the mixture hydrolyzed with saturated aqueous NH₄Cl, the aqueous layer extracted with Et₂O, and the combined organic layer and extract distilled gave 15.9 g. (40%) CF₃CHEtCH₂CO₂Et, b₂₅ 62.0-5.0°, n²⁰_D 1.3750, d₂₅ 1.110. Freshly distilled (iso-PrO)₃Al (5.5 g.) and 10 g. II heated slowly at 65-70° and 100 mm. pressure, the mixture kept 1 hr. at this temperature while slowly distilling off some iso-PrOH, heated to 110° to remove all iso-PrOH, and distilled at 20 mm. to remove 1.3 g. II, the residue treated at 65° and 100 mm. dropwise with 16.3 g. p-MeOC₆H₄CHO, and the mixture distilled gave 3.0 g. CF₃CH:CHCHO, clear, water white liquid, b₇₀ 70-6°; 2,4-dinitrophenylhydrazone, m. 226.0°.

Journal of the American Chemical Society published new progress about 83706-94-9. 83706-94-9 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is (E)-4,4,4-Trifluorobut-2-en-1-ol, and the molecular formula is C4H5F3O, COA of Formula: C4H5F3O.

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

Collins, Ian published the artcileN-alkenyl nitrone dipolar cycloaddition routes to piperidines and indolizidines. Part 6. Allylic stereocontrol in the intramolecular cyclization of monosubstituted nitrones, Related Products of alcohols-buliding-blocks, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1994), 2205-15, database is CAplus.

The intramol., thermal dipolar cycloadditions of the (Z)-N-alk-4-enyl nitrones I (R = OMe, MeOCH₂O, alkylsiloxy) bearing a single, allylic substituent were investigated. Certain alkoxy substituted nitrones I showed a remarkable preference for the formation of axially substituted isoxazolidines II (same R), whereas the Pr and trifluoromethyl substituted nitrones I (R = F₃C, Pr) gave equatorially substituted cycloadducts resp., consistent with the involvement of chair-like transition states.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about 83706-94-9. 83706-94-9 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is (E)-4,4,4-Trifluorobut-2-en-1-ol, and the molecular formula is C4H5F3O, Related Products of alcohols-buliding-blocks.

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

Dumitrescu, Lidia published the artcileSynthesis and cytotoxic activity of fluorinated analogs of Goniothalamus lactones. Impact of fluorine on oxidative processes, Safety of (E)-4,4,4-Trifluorobut-2-en-1-ol, the publication is European Journal of Medicinal Chemistry (2010), 45(7), 3213-3218, database is CAplus and MEDLINE.

Novel fluorinated analogs of goniothalamin I (R = Ph) and howiinol A II (R = Ph) were prepared from trifluorocrotonate derivatives Trifluoromethyl-goniothalamin (R/S) derivative I (R = CF₃) showed a slightly lower activity than 1, while the trifluoromethyl-howiinol A derivative II (R = CF₃) exhibited similar activities on several cell lines in the micromolar range. Unlike (R)-goniothalamin and howiinol A, trifluoromethyl parent compounds remained unchanged when submitted to biomimetic oxidative systems.

European Journal of Medicinal Chemistry published new progress about 83706-94-9. 83706-94-9 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is (E)-4,4,4-Trifluorobut-2-en-1-ol, and the molecular formula is C4H5F3O, Safety of (E)-4,4,4-Trifluorobut-2-en-1-ol.

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

Sam, Brannon published the artcileRuthenium-Catalyzed C-C Coupling of Fluorinated Alcohols with Allenes: Dehydrogenation at the Energetic Limit of β-Hydride Elimination, Product Details of C4H5F3O, the publication is Angewandte Chemie, International Edition (2015), 54(18), 5465-5469, database is CAplus and MEDLINE.

Ruthenium(II) complexes catalyze the C-C coupling of 1,1-disubstituted allenes and fluorinated alcs. to form homoallylic alcs. bearing all-carbon quaternary centers with good to complete levels of diastereoselectivity. Whereas fluorinated alcs. are relatively abundant and tractable, the corresponding aldehydes are often not com. available because of their instability.

Angewandte Chemie, International Edition published new progress about 83706-94-9. 83706-94-9 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is (E)-4,4,4-Trifluorobut-2-en-1-ol, and the molecular formula is C4H5F3O, Product Details of C4H5F3O.

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