933-35-7Relevant articles and documents
Preparation and reactions of optically active cyanohydrins derived from 4-chlorobenzaldehyde, cyclohexanone and 2-methylcyclohexanone using the (R) hydroxynitrile lyase from Prunus amygdalus
Yosef,Elmasry,Ismael, Eman H. I.,Mahran
, p. 745 - 755 (2013/05/21)
CYANURATION of 4-chlorobenzaldehyde (1), cyclohexanone (2a) and 2-methylcyclo-hexanone (2b) yielded the racemic 2-hydroxy-2-(4-chlorophenyl) ethanenitrile (R,S)-3, cyclohexanone cyanohydrin 21a and (R,S)-2- methylcyclohexanone cyanohydrin (R,S)-21b. The same reaction can be completed by using acetone cyanohydrin (4) as a transcyanating agent. The optically active cyanohydrins (R)-3 and (R)-21b could be respectively obtained by hydrocyanation of 1 and 2b using (R)-hydroxynitrile lyase (R) PaHNL [EC 4.1.2.10] from almonds (Prunus amygdalus) as a chiral catalyst. Cyanohydrins 3 and 21 in their racemic and optically active forms undergo a number of transformations which involve either the hydroxyl group or the cyanide function. Moreover, derivatization of 3 and 21b with (S)-Naproxen chloride (S)-7 gave the respective diastereoisomers 8 and 22b. The optical activities of (R)-3 and 21b as well as their derivatives were recorded. The postulated structures of the new products were supported with compatible elementary and spectroscopic (IR, 1H NMR, 13C NMR, MS and X-ray crystallography) analyses. The antitumor activity of some selected racemic new products and their respective optically active analogues were undertaken. The structure-activity relationship (SAR) was also discussed.
Highly efficient trialkylsilylcyanation of aldehydes, ketones and imines catalyzed by a nucleophilic N-heterocyclic carbene
Kano, Taichi,Sasaki, Kouji,Konishi, Teppei,Mii, Haruka,Maruoka, Keiji
, p. 4615 - 4618 (2007/10/03)
The synthetic utility of N-heterocyclic carbenes was demonstrated by the trialkylsilylcyanation of aldehydes, ketones and imines. In the presence of a catalytic amount of 3a, the reactions with Me3SiCN proceeded smoothly to give the corresponding cyanohydrin trimethylsilyl ethers or amino nitrile derivatives in good to excellent yields.
Synthesis of All Eight Stereoisomers of the Germination Stimulant Sorgolactone
Sugimoto, Yukihiro,Wigchert, Suzanne C. M.,Thuring, Jan Willem J. F.,Zwanenburg, Binne
, p. 1259 - 1267 (2007/10/03)
The naturally occurring sesquiterpene sorgolactone (2) belongs to the class of "strigolactones", which are highly potent germination stimulants for seeds of the parasitic weeds Striga and Orobanche. The aim of the present work was to synthesize all eight
