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

【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.

参考文献中间体

合成目标

【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