Category: 20117-47-9

Bertranne, M. published the artcileStructure of C₄H₇O⁺ ions obtained by fragmentation of 1-methylcyclobutanol, SDS of cas: 20117-47-9, the publication is Tetrahedron Letters (1984), 25(2), 211-14, database is CAplus.

Fragmentation patterns from the mass spectra of the title compound demonstrate that the loss of Me leads competitively to three different ions: protonated cyclobutanone, [n-C₃H₇CO]⁺, and protonated Me vinyl ketone.

Tetrahedron 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, SDS of cas: 20117-47-9.

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

Brown, Herbert C. published the artcileChemical effects of steric strain. VI. The effect of ring size on the rate of solvolysis of the 1-chloro-1-methylcycloalkane, Name: 1-Methylcyclobutan-1-ol, the publication is Journal of the American Chemical Society (1952), 1894-1902, database is CAplus.

cf. C.A. 48, 562d. Cyclic compounds undergoing reaction at a ring atom exhibit striking changes in reactivity with variation in ring size. These differences in chem. behavior are attributed to the changes in internal strain in the cyclic structures which accompany changes in the coördination number of the ring atom undergoing reaction (I-strain). 1-Chloro-1-methylcycloalkanes with C₄ to C₁₁ (inclusive), C₁₃, C₁₅, and C₁₇ rings were synthesized and the rates of solvolysis in 80% aqueous EtOH determined (k₁ at 25°). The rate of solvolysis for 1-chloro-1-methylcyclobutane (I) is relatively slow (0.00224/hr.), much slower than open-chain tertiary chlorides. 1-Chloro-1-methylcyclopentane (II) and -heptane (III) undergo solvolysis at a relatively fast rate (1.32 and 1.15/hr., resp.), whereas the corresponding cyclohexane (IV) derivative is slow (0.0106/hr.). The rates reach a maximum with the 8-membered ring (3.30/hr.) and then decrease to become essentially constant at 0.02-0.03/hr. with rings of 13 or more members. The results are in agreement with the predictions based upon the I-strain concept. Methylcyclopropane (V) was chlorinated photochemically at -20° in an attempt to synthesize 1-chloro-1-methylcyclopropane. The reaction yielded cyclopropylcarbinyl chloride (VI), b₇₃₆ 85.5-5.7°, n²⁰_D 1.4349, d₂₀ 0.981; VI via the Grignard reagent yielded an acid, b₂₀ 90-100, n²⁰_D 1.4350-1.4358; amide, m. 103-4°; p-bromophenacyl ester, m. 59.5-60.5°. VI in solvolysis studies behaved as a typical tertiary halide (0.00067/hr.). Reduction of pentaerythrityl bromide with Zn yielded 85-94% hydrocarbon mixture Methylenecyclobutane (b₇₄₄ 42.0°, n²⁰_D 1.4209) treated with HCl at 0° yielded 89% I, b₇₄₂ 89.5-91.4°, n²⁰_D 1.4310. I (9.2 g.) and 75 cc. water refluxed (the mixture was kept neutral by addition of 0.1N NaOH) and the product extracted with Et₂O yielded 54% 1-methylcyclobutanol, b₇₄₂ 116-18°, n²⁵_D 1.4333. HOCH₂CH₂CHMeOH (VII) and HBr at 100° yielded 67% CH₂BrCH₂CHBrMe (VIII), b₅₀ 87-92°, n²⁰_D 1.5080-1.5089. VII and PBr₃ yielded 77% VIII. VIII and Zn in aqueous EtOH yielded 70-88% V. Cyclopentanone (from adipic acid) with MeMgBr yielded 1-methylcyclopentanol (IX), b₇₄₅ 133-6°, m. 32-4°. IX yielded II, b₁₂₁ 66°, n²⁰_D 1.4467. Cyclohexanone yielded the tertiary alc. (X), b₂₉ 72-3.5°, n²⁰_D 1.4609. X yielded IV, b₁₀₀ 83-4°, n²⁰_D 1.4578. Cycloheptanone (b₇₄₇ 172-4°, n²⁰_D 1.4613) yielded 1-methylcycloheptanol (XI), b₂₀ 82-3.5°, n²⁰_D 1.4960. XI with dry HCl yielded 83% III, b_20.5 77-7.5°, n²⁰_D 1.4710. Cycloöctanone (4.06 g.) in 50 cc. Et₂O added MeMgI (from 14.2 g. MeI in 30 cc. Et₂O and 2.43 g. Mg in 15 cc. Et₂O) during 45 min., the mixture refluxed 4 hrs., titrated with saturated NH₄Cl, and the Et₂O evaporated in vacuo yielded 2 g. 1-methylcyclöctanol (XII), m. 34-6°. Distillation of XII yielded 1-methylcycloöctene (XIII), b₇₄₁ 159-64°, n²⁰_D 1.4710. XIII with HCl at 0° yielded the chloride b₄ 64-5°, n²⁰_D 1.4796. Di-Me azelate (b₁₀ 142-50°, n²⁰_D 1.4350-1.4363) by the method of Prelog, et al. (C.A. 42, 1893g), and Stoll, et al. (C.A. 42, 3741dh), yielded 26% crude acyloin fraction (XIV), b₁₂ 110-24°. XIV with Zn-HCl yielded 61% cyclononanone (XV), b₁₂ 92-6°, n⁴⁰_D 1.4682-1.4696. XV (9.8 g.) added during 2 hrs. to 0.21 mole Me Grignard reagent and the mixture refluxed 6 hrs. yielded 6.42 g. 1-methylcyclohexanol (XVI), m. 51-2°. XVI treated 2 hrs. at room temperature with HCl yielded 1-chloro-1-methylcyclononane. Sebacoin (b_0.1 75-85°, m. 36-7.5°, n⁵⁵_D 1.4788) on reduction yielded 73% ketone fraction (b₁₂ 95-112°), which on fractionation (b₁₂106-9°) m. 22-4°, n³⁰_D 1.4784. 1-Methylcyclodecanol (39% yield) m. 52.5-3.1°, Di-Me hendecanedioate (b₃139-50°, n²⁰_D 1.4379-91) yielded 61% acyloin fraction, b_0.08 88-93°, n⁵⁵_D 1.4803, m. 29-32°, which on reduction yielded 55% ketone fraction, b₁₂ 114-20°, n²⁰_D 1.4811; semicarbazone, m. 200-1°. Cycloundecanone (0.05 mole) and 0.15 mole MeMgI yielded 0.60 g. crystalline product, m. 128.5-9.5°, and 5.92 g. 1-methylcycloundecanol, m. 40-2°. For the larger rings, the ketone, its m.p., the tertiary alc., % yield, and m.p. are: cyclotridecanone, 30°, 1-methylcyclotridecanol, 92, 75.5-6.5°; cyclopentadecanone, 61.5-4.5°, 1-methyl-cyclopentadecanol, 80, 83.5-85°; cycloheptadecanone, 58-60°, 1-methylcycloheptadecanol, 92, 77.5-8.5°. -Am MgCl and EtOAc yielded the tertiary alc., b₂ 84.5-6.5°, n²⁰_D 1.4401; diamylmethylcarbinyl chloride was prepared

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

Clemens, Jennifer published the artcileSelective N2-Alkylation of 1H-Indazoles and 1H-Azaindazoles, SDS of cas: 20117-47-9, the publication is Synthesis (2022), 54(14), 3215-3226, database is CAplus.

A general and selective procedure for the N2-alkylation of 1H-indazoles and 1H-azaindazoles is presented. Promoted by either trifluoromethanesulfonic acid or copper(II) triflate, diverse 1H-indazoles/azaindazoles are selectively alkylated with varied primary, secondary, and tertiary alkyl 2,2,2-trichloroacetimidates at the N2-nitrogen to afford the corresponding 2-alkyl-2H-indazoles/azaindazoles. Forty-one examples are included along with a discussion of reaction optimization, scope, and mechanism.

Synthesis 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, SDS of cas: 20117-47-9.

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

Chernykh, S. P. published the artcileHydration of methylenecyclobutane under static conditions., Application In Synthesis of 20117-47-9, the publication is Khimicheskaya Promyshlennost (Moscow, Russian Federation) (1987), 716-18, database is CAplus.

The title hydration in an unstirred reactor containing KU-23 or KU-2-8chS at room temperature with 1.5-4:3.5-8:1 catalyst-H₂O-methylenecyclobutane (I) gave 1-methyl-1-cyclobutanol (II) as the major product, along with its sym. ether. Increasing amounts of olefinic impurities in I lowered the quality of II, owing to formation of alc. and unsym. ether byproducts. Polymeric byproducts were obtained with catalysts containing â‰?5% H₂O.

Khimicheskaya Promyshlennost (Moscow, Russian Federation) 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, Application In Synthesis of 20117-47-9.

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

Kurouchi, Hiroaki published the artcileControlling Selectivity by Controlling Energy Partitioning in a Thermal Reaction in Solution, HPLC of Formula: 20117-47-9, the publication is Journal of the American Chemical Society (2016), 138(44), 14534-14537, database is CAplus and MEDLINE.

The comparison of exptl. and predicted kinetic isotope effects in the α-cleavage of alkoxy radicals is used here to judge the applicability of statistical rate theories. It is found that the governing rate theory and the statistical vs. nonstatistical nature of the cleavage depend on the cleavage barrier and how much energy is imparted to the radical. The latter can then be controlled by changing the size of substituents in the system. With a large alkyl group substituent, the vibrational energy of the alkoxy radical is increased, but this energy is not statistically distributed, leading to a lower isotope effect than predicted by statistical theories. The observed isotope effect can be approx. rationalized using a semistatistical localized RRKM model.

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, HPLC of Formula: 20117-47-9.

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