3-Hydroxypregn-16-en-20-one | 31686-13-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3-Hydroxypregn-16-en-20-one
• 英文别名: 1-[(8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
• CAS: 31686-13-2
• 化学式: C₂₁H₃₂O₂
• 分子量: 316.484
• InChiKey: SFXPZLCQRZASKK-BEJJEYDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Hydroxypregn-16-en-20-one 、 乙酰化葡萄烯糖 在 trichloro(trifluoromethanesulfonato)titanium(IV) 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以58%的产率得到[(2R,3S,6S)-6-[[(8R,9S,10S,13S,14S)-17-acetyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3-acetyloxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
  参考文献：
  名称：

  An efficient procedure for the synthesis of 2,3-unsaturated-O-glycosides: TiCl3(OTf) as the catalyst for type I Ferrier rearrangement

  摘要：

  An efficient type I Ferrier rearrangement reaction system for the synthesis of 2,3-unsaturated-O-glycosides has been established by using TiCl3(OTf) as the catalyst. A series of 2,3-unsaturated-O-glucosides were prepared from 3,4,6-tri-O-acetyl-D-glucal in good yield and high anomeric selectivity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.051

文献信息

• Production process for 16-dehydropregnenoneol and its analogs
  申请人：Tian Weisheng

  公开号：US20060166955A1

  公开（公告）日：2006-07-27

  The present invention relates to a clean process for the degradation of steroidal sapogenin to produce 16-dehydropregnenolone and its analogs. The pure or the crude pseudo steroidal sapogenin, derived from steroidal sapogenin, dissolved in organic solvent, reacts with hydrogen peroxide with or without metal compound and acid as catalyst, and the crude products directly go through elimination and hydrolization in the presence of base to give 16-Dehydropregnenolone or its analog, accompanied with the other product 4R(or S)-methyl-5-hydroxy-pentate, which is converted to 4R(or S)-methyl-δ-pentyl lactone after acidification and extraction from the water layer. This technology improved the utilizing degree of steroidal sapogenin, improved the yield, and cleared up the chromium pollution in the former technique. In a word, the method disclosed in this invention is more suitable for manufacture.

  本发明涉及一种用于降解类固醇皂甙生成16-去氢孕酮和其类似物的清洁工艺。从类固醇皂甙中提取的纯或粗假类固醇皂甙，溶解在有机溶剂中，与过氧化氢反应，可以加入金属化合物和酸作为催化剂，粗产品直接在碱的存在下经过消除和水解，得到16-去氢孕酮或其类似物，伴随另一产品4R（或S）-甲基-5-羟基-戊酸酯，经过酸化和从水层中提取后转化为4R（或S）-甲基-δ-戊内酯。这种技术提高了类固醇皂甙的利用率，提高了产量，并清除了以前技术中的铬污染。总之，本发明揭示的方法更适合生产。
• PHARMACEUTICALLY ACCEPTABLE SALTS OF 5.ALPHA.-PREGN-16-EN-3.BETA.-OL-20-ONE 3-SULPHATE ESTER WITH PROGESTIN ACTIVITY AND USEFUL IN THE TREATMENT OF CNS DISORDERS
  申请人：Wyeth

  公开号：EP0980381B1

  公开（公告）日：2003-08-06
• PHARMACEUTICALLY ACCEPTABLE SALTS OF 5ALPHA-PREGNAN-3BETA, 16ALP HA-DIOL-20-ONE 3-SULFATE USEFUL AS PROGESTINS AND CNS DISORDERS
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP0981538A1

  公开（公告）日：2000-03-01
• US5998638A
  申请人：——

  公开号：US5998638A

  公开（公告）日：1999-12-07
• US6713465B1
  申请人：——

  公开号：US6713465B1

  公开（公告）日：2004-03-30