Facile Synthesis of 4-Carbethoxycyclohexanone

Sánchez, I. H.; Ortega, Armando; Garcı́a, Gabriel; Larraza, M. I.; Flores, Humberto

doi:10.1080/00397918508076820

Cited by 13 publications

(10 citation statements)

References 15 publications

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“…Compound (I) was prepared by the method of Sanchez et al (1985) from 2-methoxycarbonyl-4,4-di-tert-butoxycarbonylcyclohexanone. Crystals were grown by slow evaporation of a dimethyl sulfoxide solution.…”

Section: Methodsmentioning

confidence: 99%

Di-tert-butyl 4-oxocyclohexane-1,1-dicarboxylate

et al. 2006

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Section: Methodsmentioning

confidence: 99%

Di-tert-butyl 4-oxocyclohexane-1,1-dicarboxylate

et al. 2006

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“…l-[2-Hydroxy-4-[(5-hydroxy-3,3-dimethylpentyl)oxy]-3propylphenyl]ethanone (21). A mixture of 3.7 g (28 mmol) of 3,3-dimethyl-l,5-pentanediol,48 1.95 mL (21.4 mmol) of dihydropyran, 0.2 g of p-toluenesulfonic acid monohydrate, and 30 mL of THF was stirred for 18 h at room temperature and then worked up with saturated NaHCOg solution and ethyl acetate in the usual manner.…”

Section: Methodsmentioning

confidence: 99%

3,4-Dihydro-2H-1-benzopyran-2-carboxylic acids and related compounds as leukotriene antagonists

Cohen

Weber²,

Banner³

et al. 1989

J. Med. Chem.

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Evaluation of a series of 3,4-dihydro-2H-1-benzopyran-2-carboxylic acids linked to the 2-hydroxyacetophenone pharmacophore present in the standard peptidoleukotriene antogonist FPL 55712 (1) has led to the discovery of Ro 23-3544 (7), an antagonist possessing greater potency and duration of action vs LTD4 than the standard (aerosol route of administration, guinea pig bronchoconstriction model). Interestingly, this compound also potently inhibited bronchoconstriction induced by LTB4 whereas 1 did not. Attempts to establish structure--activity relationships in this series involved modifications in the 2-hydroxyacetophenone moiety, the linking chain, and the chroman system. All variations produced analogues which were either inactive or possessed reduced potency relative to acid 7. Optical resolution of 7 was achieved by two methods. Absolute configurations of the enantiomers were determined via X-ray crystallographic analyses of an intermediate as well as a salt of the S enantiomer. Although the enantiomers exhibited similar potencies in in vitro assays and in vivo when administered intravenously, significant differences were observed in the guinea pig bronchoconstriction model vs LTC4 and LTD4 when administered by the aerosol route (S antipode 15-fold more potent). The properties of 7 have been compared with several recently reported leukotriene antagonists.

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“…As a proof-of-concept experiment, we chose to generate radical 9 from the thiohydroxamate (Kim ester) precursor (11), 20 itself prepared following Scheme 4. To that end ethyl 4-hydroxycyclohexanecarboxylatey ( 12) 21 was treated with methanesulfonyl chloride to afford the corresponding mesylate (13) in 94% yield. Further reaction with sodium benzylselenoate followed by hydrolysis and then N,S-dimethyl-N-hydroxydithiocarbamate 22 afforded 11 in 32% yield (three steps).…”

Section: Chemcommmentioning

confidence: 99%

7-Selenabicyclo[2.2.1]heptane

et al. 2012

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a b s t r a c tAb initio and density functional theory (DFT) calculations predict that intramolecular homolytic substitution by alkyl radicals at the selenium atom in seleninates proceeds through smooth transition states in which the attacking and leaving radicals adopt a near collinear arrangement. When forming a fivemembered ring and the leaving radical is methyl, G3(MP2)-RAD calculations predict that this reaction proceeds with an activation energy (DE 1 z ) of 30.4 kJ mol . Homolytic addition to the phenyl group was found not to be competitive with substitution, with a calculated barrier of 57.6 kJ mol À1. This computational study provides insight into homolytic substitution chemistry involving seleninates.

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Facile Synthesis of 4-Carbethoxycyclohexanone

Cited by 13 publications

References 15 publications

Di-tert-butyl 4-oxocyclohexane-1,1-dicarboxylate

Di-tert-butyl 4-oxocyclohexane-1,1-dicarboxylate

3,4-Dihydro-2H-1-benzopyran-2-carboxylic acids and related compounds as leukotriene antagonists

7-Selenabicyclo[2.2.1]heptane

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