Journal of the Chemical Society. Perkin transactions II p. 965 - 970 (1990)
Update date:2022-08-02
Topics:
Longridge, Jethro L.
Nicholson, Stuart
The kinetics of hydrolysis of (5Z)-7-(<2RS,4RS,5SR>-4-o-hydroxyphenyl-2-trifluoromethyl-1,3-dioxan-5-yl)hept-5-enoic acid, ICI 185282 (1a), have been studied.At low pH the compound undergoes conventional acid-catalyzed hydrolysis of the dioxane ring.However, under alkaline conditions, a second reaction is observed.Studies by NMR show that this process involves a quite unexpected intramolecular hydride transfer from a carbon atom carrying a strongly electron-withdrawing trifluoromethyl substituent.Additional studies on closely related compounds are reported and a mechanism involving a ring-opened quinone methide intermediate is proposed.
View MoreWuhan Soleado Technology Co.,Ltd.
Contact:86-2783341481 18971291927
Address:RM2405 Unit 1 Builing 1, Taiyin Tower, Changqing Road,Wuhan China
website:http://www.acrospharmatech.com
Contact:+1-3234804688
Address:Flat/RM 1502,Easey Commercial building 253-261 Hennessy Road,Wanchai，HongKong
Shijiazhuang Haitian Amino Acid Co., Ltd.
Contact:+86-311-88908111
Address:Shijiazhuang Hebei province,China
Suzhou SuKaiLu Chemical Technology Co., Ltd.
Contact:+86-512-62766020
Address:Floor 4, Building 1, Xinyi Pharmaceutical Valley Wisdom Industrial Park, 415 Changyang Street, Suzhou Industrial Park, Jiangsu Province
Shanghai WinTide BioTechnology Co.,Ltd
Contact:86-21-37100630
Address:No. 908 Yunhe Road, Fengxian district, Shanghai
Doi:10.1021/jo00001a077
(1991)Doi:10.1016/0031-9422(90)85174-E
(1990)Doi:10.1021/jm300603y
(2012)Doi:10.1055/s-0030-1258451
(2011)Doi:10.1002/prac.19983400110
(1998)Doi:10.1007/BF00962396
(1990)
