• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】33619

【品名】(8S,13R,14S)-13-ethyl-7,8,13,14,15,16-hexahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,6H)-dione

【CA登记号】

【 分 子 式 】C19H22O2

【 分 子 量 】282.38248

【元素组成】C 80.82% H 7.85% O 11.33%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(I)

Compound can be prepared in two different ways: 1) By dehydration of 13beta-ethyl-11beta,17beta-dihydroxy-17alpha-ethynyl-gona-4,9-diene-3-one (IV) with 60% formic acid at 100 C or with perchloric acid in methylene chloride containing acetonitrile. 2) The ketalization of 13beta-ethyl-gona-4,9,11-triene-3,17-dione (I) by means of glycol (A) and oxalic acid in dichloroethane affords 3-ethylenedioxy-13beta-ethyl-gona-4,9,11-trien-17-one (II), which is then treated with methylmagnesium bromide (B) and acetylene (C) in THF to yield 3-ethylenedioxy-13beta-ethyl-17beta-hydroxy-17alpha-ethynyl-gona-4,9,11-triene (III). Finally, this compound is hydrolyzed in an acidic medium.

1 Bertin, D.; Pierdet, A.; 19-Nor-delta(4,9,11)-gonatriene-3-ones. DE 1618810; FR 1503984; GB 1128787; US 3484462 .
2 Bertin, D.; Pierdet, A; Process for the preparation of unsaturated 19-nor steroids. DE 1618815; FR 1479352; GB 1128788; US 3478067 .
3 Nomine, G.; et al.; New Steroid compounds, compositions incorporating them and processes for their preparation. GB 1069709 .
4 Nomine, G.; et al.; Novel 13beta-alkyl-4,9,11-gonatriene-3-ones. DE 1291337; DE 1593307; FR 1426077; FR 1453214; FR 1492782; NL 6607609; US 3248294; US 3257278 .
5 Castaner, J.; Thorpe, P.; R-2323. Drugs Fut 1977, 2, 2, 131.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 11295 Polyethylene glycol;1,2-Ethanediol;Monoethylene glycol; Ethylene glycol 107-21-1 C2H6O2 详情 详情
(B) 33623 bromo(methyl)magnesium 75-16-1 CH3BrMg 详情 详情
(I) 33619 (8S,13R,14S)-13-ethyl-7,8,13,14,15,16-hexahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,6H)-dione C19H22O2 详情 详情
(II) 33620   C21H26O3 详情 详情
(III) 33621   C23H28O3 详情 详情
(IV) 33622 (8S,11S,13S,14S,17R)-13-ethyl-17-ethynyl-11,17-dihydroxy-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one C21H26O3 详情 详情
(C) 23634 acetylene 74-86-2 C2H2 详情 详情
Extended Information