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 MoreBeijing Cooperate Pharmaceutical Co.,Ltd
website:http://www.cooperate-pharm.com/
Contact:86-01060279497
Address:No.507,Building 4,Tianhua Street, Biomedicine industrial Base
Sanming Coffer Fine Chemical Industrial Co., Ltd
website:http://www.cofferxm.com/
Contact:+86-598-5853979
Address:Jin-sha Yuan Chuang-ye Park,Hi-Tech Development Zone,Sanming City P.R.China
Taizhou Elitechemie MediPharma Technology Co.,Ltd.
Contact:+86-523-86810021
Address:Building G14,NO.1 Avenue,China Medical City, Taizhou, Jiangsu,China
Shanghai Yuking Water Soluble Material Tech Co., Ltd
Contact:86-21-68286299
Address:4F, 13B, No. 600, South Xinyuan Road 201306, Shanghai, China
Zhengzhou Xinlian Chemical Tech Co. ,Ltd
Contact:0371-65771781 021-52042910
Address:H Part, Building I, No. 700 Gonglu Road, Pudong New Area, 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)
