10407-33-7Relevant articles and documents
ENANTIOSELECTIVE SYNTHESIS OF α-FUNCTIONALLY-SUBSTITUTED CYCLOHEXANONES
Jeso, Bernard De,Pommier, Jean-Claude
, p. 4511 - 4514 (1980)
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Clay catalysis: Storks alkylation and acylation of cyclohexanone without isolation of enamine
Hammadi,Villemin
, p. 2901 - 2904 (1996)
Cyclohexanone and morpholine in the presence of KSF under azeotropic distillation gave 1-morpholinocyclohexane which is alkylated or acylated in situ without isolation of the enamine. The overall yield of these Stork's reactions are better or equivalent to those obtained by isolation of the enamine.
Efficient synthesis of ω-functionalized nonanoic acids
Cotarca,Delogu,Maggioni,Nardelli,Bianchini,Sguassero
, p. 328 - 332 (1997)
Starting from cyclohexanone and acrylonitrile, a four-step synthesis of the title open-chain C9 compounds is reported. An improved protocol for cyanoethylation of cyclohexanone in the presence of a catalytic amount of cyclohexylamine afforded 3-(2-oxocyclohexyl)propanenitrile (1) in 92% yield. Cyclohexaneperoxycarboxylic acid (CHPCA) is introduced as a highly efficient reagent in the Baeyer-Villiger rearrangement of 1, yielding over 90% of 2. Pyrolysis of 2 afforded under optimized conditions 3 in 92% yield and 99% regioisomeric purity, otherwise a mixture of three unsaturated isomeric ω-cyano nonenoic acids 3, 10 and 11 is obtained. Partial hydrogenation of 3 allowed the isolation of 4 in 90% yield. Hydrogenation of 4 at elevated hydrogen pressure gave 9-aminononanoic acid (5), whereas hydrolysis of 4 led to 1,9-nonanedioic acid (azelaic acid, 6). Both, 5 and 6 are valuable C9 monomers for the preparation of polyamides with specific properties.
Intramolecular Photoaddition of Alkenes to Chiral 1,3-Dioxin-4-ones: Evidence for Effect of Pyramidalization on the Facial Selectivity
Haddad, Nizar,Abramovich, Zehavit
, p. 6883 - 6887 (1995)
Intramolecular photoaddition of alkenes to chiral 1,3-dioxin-4-ones 5 present, for the first time, examples with high facial selectivity in which the addition proceeds preferentially from the less exposed side (b-side) under kinetic control conditions.This unprecedented facial selectivity cannot be explained only on the basis of steric effects; however, it is consistent with the direction of pyramidalization in structure 3.It can be concluded that the geometry of the pyramidalized Cβ in the triplet excited dioxinones plays an important role in defining the facial selectivity in this reaction.However, steric effect cannot be neglected in rationalizing the facial selectivity as found by comparing the facial selectivity obtained in the irradiation of the studied compounds.
A practical synthetic route to enantiopure 6-substituted cis-decahydroquinolines
Amat, Mercedes,Navio, Laura,Llor, Nuria,Molins, Elies,Bosch, Joan
supporting information; experimental part, p. 210 - 213 (2012/03/10)
Starting from 4-substituted cyclohexanones, a practical synthetic route to enantiopure 6-substituted cis-decahydroquinolines has been developed, the key steps being a stereoselective cyclocondensation of an unsaturated δ-keto ester derivative with (R)-phenylglycinol and the stereoselective hydrogenation of the resulting tricyclic oxazoloquinolone lactams.
Preparation of sixteen 3-hydroxy-4- and 7-hydroxy-1-hydrindanones and 3-hydroxy-4- and 8-hydroxy-1-hydroazulenones
Tsantali, Georgia G.,Dimtsas, John,Tsoleridis, Constantinos A.,Takakis, Ioannis M.
, p. 258 - 265 (2007/10/03)
3-Hydroxyoctahydro-4H-inden-4-ones and 7-hydroxyoctahydro-1H-inden-1-ones (1, 2 and 3, 4, respectively), as well as the homologous 3-hydroxyoctahydro- 4(1H)-azulenones (5, 6) and 8-hydroxyoctahydro-1(2H)-azulenones (7, 8), were prepared diastereoselective
