Category: 20117-47-9

Nageswara Rao, Desaboini published the artcileDiscovery of Quinoxaline-Based P1-P3 Macrocyclic NS3/4A Protease Inhibitors with Potent Activity against Drug-Resistant Hepatitis C Virus Variants, Recommanded Product: 1-Methylcyclobutan-1-ol, the publication is Journal of Medicinal Chemistry (2021), 64(16), 11972-11989, database is CAplus and MEDLINE.

The three pan-genotypic HCV NS3/4A protease inhibitors (PIs) currently in clin. use-grazoprevir, glecaprevir, and voxilaprevir-are quinoxaline-based P2-P4 macrocycles and thus exhibit similar resistance profiles. Using our quinoxaline-based P1-P3 macrocyclic lead compounds as an alternative chem. scaffold, we explored structure-activity relationships (SARs) at the P2 and P4 positions to develop pan-genotypic PIs that avoid drug resistance. A structure-guided strategy was used to design and synthesize two series of compounds with different P2 quinoxalines in combination with diverse P4 groups of varying sizes and shapes, with and without fluorine substitutions. Our SAR data and cocrystal structures revealed the interplay between the P2 and P4 groups, which influenced inhibitor binding and the overall resistance profile. Optimizing inhibitor interactions in the S4 pocket led to PIs with excellent antiviral activity against clin. relevant PI-resistant HCV variants and genotype 3, providing potential pan-genotypic inhibitors with improved resistance profiles.

Journal of Medicinal 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 C5H10O, Recommanded Product: 1-Methylcyclobutan-1-ol.

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

Zak, Mark published the artcileMinimizing CYP2C9 Inhibition of Exposed-Pyridine NAMPT (Nicotinamide Phosphoribosyltransferase) Inhibitors, COA of Formula: C5H10O, the publication is Journal of Medicinal Chemistry (2016), 59(18), 8345-8368, database is CAplus and MEDLINE.

NAMPT inhibitors may show potential as therapeutics for oncol. Throughout our NAMPT inhibitor program, we found that exposed pyridines or related heterocyclic systems in the left-hand portion of the inhibitors are necessary pharmacophores for potent cellular NAMPT inhibition. However, when combined with a benzyl group in the center of the inhibitors, such pyridine-like moieties also led to consistent and potent inhibition of CYP2C9. In an attempt to reduce CYP2C9 inhibition, a parallel synthesis approach was used to identify central benzyl group replacements with increased Fsp3. A spirocyclic central motif was thus discovered that was combined with left-hand pyridines (or pyridine-like systems) to provide cellularly potent NAMPT inhibitors with minimal CYP2C9 inhibition. Further optimization of potency and ADME properties led to the discovery of compound 68, a highly potent NAMPT inhibitor with outstanding efficacy in a mouse tumor xenograft model and lacking measurable CYP2C9 inhibition at the concentrations tested.

Journal of Medicinal 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 C4H12ClNO, COA of Formula: C5H10O.

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

Yang, N. C. published the artcilePhotochemical reactions of ketones in solution, Formula: C5H10O, the publication is Journal of the American Chemical Society (1958), 2913-14, database is CAplus.

The light-induced reactions of simple aliphatic ketones in saturated hydrocarbons were studied. Ketones with no γ-H atom gave the corresponding alc. and the addition product with the hydrocarbon. Ketones with γ-H atoms gave Me₂CO, an olefin, and a cyclobutanol derivative These reactions differ markedly from those previously observed in the gas phase. The formation of cyclobutanols offers a route to a group of compounds otherwise difficult to prepare A 1:8 mixture of Me₂CO and cyclohexane (I) irradiated in quartz yielded a small amount of CH₄ and CO. Fractional distillation and gas chromatography yielded Me₂CHOH 53, pinacol 15, MeCOCH₂COMe 8, and cyclohexyldimethylcarbinol 12%; cyclohexylcyclohexene and hydrocarbon polymers were also obtained. The recovered I showed slight unsaturation Similarly, irradiation of 2-pentanone in I gave Me₂CO, C₂H₄, and 1-methylcyclobutanol (phenylurethan m.p. 141°). Irradiation of 2-octanone in isoöctane gave equimol. amounts of Me₂CO and CH₂:CHPr (67%), and 17% 1-methyl-2-propylcyclobutanol b₉ 67-8°, n_D²⁰ 1.4420, phenylurethan m. 78deg;. Irradiation of 2-nonanone in isoöctane yielded Me₂CO, 1-hexene, and 1-methyl-2-butylcyclobutanol, b_0.8 49-50°, n_D²⁰ 1.4441, phenylurethan m.p. 91°. An intramol, mechanism is formulated for the formation of cyclobutanols.

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 C8H8O2, Formula: C5H10O.

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

Cecchi, Patrizio published the artcileGas-phase protonation of spiropentane. A novel entry into the C₅H₉⁺ potential energy surface, Safety of 1-Methylcyclobutan-1-ol, the publication is Journal of the American Chemical Society (1993), 115(22), 10338-47, database is CAplus.

The structures, stabilities, and isomerization patterns of C₅H₉⁺ ions arising from the gas-phase protonation of spiropentane have been investigated by nuclear-decay, radiolytic, and FT-ICR techniques combined with ab initio calculations The exptl. and theor. results are consistent with the initial formation of a corner-protonated spiropentane intermediate 17, whose lifetime in the gas phase exceeds 7 × 10^-9 s. This local C₅H₉⁺ min. is separated from the ca. 30 kcal mol^-1 more stable cyclopentyl cation as well as from dimethylallyl open-chain isomers by significant energy barriers. Persistence of 17 in the gas phase does not find any correspondence in solution Solvation and ion-pairing effects may explain the failure to detect C₅H₉⁺ structures retaining the spirobicyclic framework of spiropentane in the condensed phase.

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, Safety of 1-Methylcyclobutan-1-ol.

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

Hill, E. Alexander published the artcileRing cleavage rearrangement of cyclobutylmethylboranes, Computed Properties of 20117-47-9, the publication is Journal of Organometallic Chemistry (1982), 239(2), 279-92, database is CAplus.

Boranes prepared by hydroborating methylenecyclobutane (I) with BH₃-THF, 9-borabicyclo[3.3.1]nonane, and BH₃-Me₂S rearranged on heating at 100-160° to open chain structures. Products after oxidation were the unrearranged cyclobutylmethanol, and 4-penten-1-ol (II), 1,4-pentanediol (III) and 1,5-pentanediol (IV). II was the major product when stoichiometric alkene:BH bonds was used; III and IV were formed with excess BH₃. The rate of rearrangement using BH₃-Me₂S at 100° in triglyme was not significantly dependent upon the initial I-BH₃ ratio (3/1 or 1.15/1) or the presence of excess Me₂S. However, an equivalent amount of pyridine prevented rearrangement. Rearrangement in THF using BH₃-THF also occurred at comparable rates in the presence and absence of excess BH₃. Little or no isomerization of the B function into the cyclobutane ring was observed A concerted 4-center mechanism requiring a vacant B orbital was suggested.

Journal of Organometallic 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 C5H10O, Computed Properties of 20117-47-9.

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

Leroux, Yves published the artcileReaction of magnesium with γ- and δ-halogenated ketones; synthesis of cyclanols, COA of Formula: C5H10O, the publication is Comptes Rendus des Seances de l’Academie des Sciences, Serie C: Sciences Chimiques (1967), 265(25), 1472-4, database is CAplus.

The reaction of Mg with γ- and δ-halo ketones in tetrahydrofuran (THF) was investigated. Treatment of γ-chlorinated ketones with Mg in THF followed by hydrolysis gave the corresponding pinacols. Similar treatment of γ-brominated ketones at 25° gave the corresponding I (R, R1, R2 and m.p. of phenylurethane derivative given): Me, H, H, 140°; Me, Me, H, 110°; Me, Et, H, 81°; Me, H, Me, 110°; Et, H, H, 125°; Pr, H, H, 99°; Bu, H, H, 95°; pentyl, H, H, 74°. The second alc. above was 60:40 cis-trans mixture and the fourth was practically pure cis isomer. Similar treatment of a δ-bromo ketone, e.g. 1-bromo-5-hexanone, gave 65% 1-methyl-1-cyclopentanol, as well as small amounts of pinacol and non-brominated ketones. The reaction is pictured as involving a radical cleavage of C-halogen bond and a reduction of the carbonyl group to an anion radical.

Comptes Rendus des Seances de l’Academie des Sciences, Serie C: Sciences Chimiques 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, COA of Formula: C5H10O.

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

Kapustina, N. I. published the artcileOxidation of 1-methylcyclobutanol with lead(IV) and manganese(III) compounds, Quality Control of 20117-47-9, the publication is Izvestiya Akademi Nauk, Seriya Khimicheskaya (1992), 2760-3, database is CAplus.

1-Phenyl-4-pentanone is formed as the main product of reaction between 1-methylcyclobutanol (I) and Pb(OAc)₄ in benzene. Oxidation of I with Mn(OAc)₃ in AcOH leads to a mixture of Me Pr ketone and 2,9-decanedione. Reaction of I with Pb(OAc)₄ or Mn(OAc)₃ in the presence of a metal halide yields selectively the corresponding 1-substituted (chloro, bromo, thiocyano or cyano) 4-pentanone.

Izvestiya Akademi 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 C5H10O, Quality Control of 20117-47-9.

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

Van de Sande, C. C. published the artcileMetastable ion characteristics. XXXVII. Structure and formation of stable C3H6O.+ ions, Application of 1-Methylcyclobutan-1-ol, the publication is Journal of the American Chemical Society (1975), 97(16), 4617-20, database is CAplus.

The C3H6O•+ isomeric ions I, II, CH2:CHOMe•+(III), C2H5CHO•+, CH3CH:CHOH•+, CH3COCH3•+, and CH2:CH(OH)CH3•+ are stable, with lifetimes >10-5 sec, and can be identified from their collisional activation (CA) spectra. Aliphatic terminal epoxides give a mixture of ions I and III, suggesting that the rearrangements involved are stepwise, not concerted. The C3H6O•+ ions formed by the loss of CH2O from the 2-methyl- and 4-methyl-1,3-dioxolane mol. ions have structure I; in a similar manner, 1,4-dioxane yields the cyclic ion II. The results show that the size of the cyclic transition state in hydrogen rearrangements is sensitive to a number of competing factors.

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 C17H20ClN3, Application of 1-Methylcyclobutan-1-ol.

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

Tomic, L. published the artcileTris(dipivaloyemethanato)holmium induced NMR shifts, Recommanded Product: 1-Methylcyclobutan-1-ol, the publication is Croatica Chemica Acta (1971), 267-9, database is CAplus.

The NMR of 1-methylcyclobutanol and 1-octanol were studied by means of complexes of Ho and Pr with 2,2,6,6-tetramethyl-3,5-heptanedione (DPM). The complex Ho(DPM)3 is a more powerful NMR shift reagent than Eu(DPM)3 and Pr(DPM)3, but introduces considerably stronger line broadening, spin-spin splittings being observable only for the most distant protons from the coordination site.

Croatica Chemica Acta 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 C17H18N2O6, Recommanded Product: 1-Methylcyclobutan-1-ol.

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

Dickman, John published the artcileMass spectrometry in structural and stereochemical problems. CLXIX. Determination of the structures of the ions produced in the single and double McLafferty rearrangements by ion cyclotron resonance spectroscopy, Category: alcohols-buliding-blocks, the publication is Journal of the American Chemical Society (1969), 91(8), 2069-84, database is CAplus.

Two possible structural isomers of the C3H6O•+ ion produced by electron impact induced fragmentations are the keto ion Me2CO+• and the enol ion MeC(:CH2)O+H•. The electron impact induced double Mc-Lafferty rearrangement can also produce a C3H6O•+ ion which could conceivably exist in either the enol or sym. oxonium ion structure. Ion cyclotron resonance and pulsed double resonance spectroscopy are used to study the ion-mol. reactions of the keto species, generated from acetone; the enol species, generated from 2-hexanone (via a McLafferty rearrangement) and from 1-methylcyclobutanol; and the double McLafferty species, generated from 5-nonanone. Seven ion-mol. reactions are found which distinguish between the keto and enol ions, thus substantiating the proposed differences in structure. In all cases studied, the enol ion, from 2-hexanone and the enol ion from 1-methylcyclobutanol behave identically indicating their structures to be equivalent The same ion-mol. reactions which distinguish between the keto and enol isomers can be utilized to distinguish between the keto and double McLafferty species. The enol and double McLafferty species react identically in all systems studied thus suggesting identical structures and raising serious doubts about the earlier proposed existence of a sym. double McLafferty oxonium ion. Deuterium labeling is employed to distinguish between isomeric ions of identical mass.

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, Category: alcohols-buliding-blocks.

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