3-methoxy-7α-methylestra-1,3,5(10),15-tetraen-17-one | 50392-06-8

• 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-methoxy-7α-methylestra-1,3,5(10),15-tetraen-17-one
• 英文别名: 3-Methoxy-7α-methylestra-1,3,5(10),15-tetraen-17-on；(7α)-3-methoxy-7-methylestra-1,3,5(10),15-tetraen-17-one；(7alpha)-3-Methoxy-7-methylestra-1,3,5(10),15-tetraen-17-one；(7R,8R,9S,13S,14S)-3-methoxy-7,13-dimethyl-7,8,9,11,12,14-hexahydro-6H-cyclopenta[a]phenanthren-17-one
• CAS: 50392-06-8
• 化学式: C₂₀H₂₄O₂
• 分子量: 296.409
• InChiKey: ZJBVKWZZTXGAQF-MPSBBLFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methoxy-7α-methylestra-1,3,5(10),15-tetraen-17-one 生成 17β-hydroxy-3-methoxy-7α-methylestra-1,3,5(10),14-tetraene
  参考文献：
  名称：

  Selective synthesis of 14-dehydroestranes

  摘要：

  DOI：

  10.1016/0039-128x(73)90075-5
• 作为产物：
  描述：

  17,17-(ethylenedioxy)-3-methoxy-7α-methylestra-1,3,5(10),15-tetraene 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 以92%的产率得到3-methoxy-7α-methylestra-1,3,5(10),15-tetraen-17-one
  参考文献：
  名称：

  The synthesis of functionalized 13,14-seco-steroids via Grob fragmentation

  摘要：

  A synthetic methodology for the synthesis of 13,14-seco-steroids with substituents at C-14 and C-17 is described. The approach involves Grob fragmentation of 14beta-hydroxy-17beta-tosylates, hydroboration-oxidation of the intermediate Delta(13(17))-olefin, and hydride reduction of the 14-ketone. An unambiguous structural assignment of (13R,14S,17S)-14,17-diacetoxy-3-methoxy-7alpha-methyl-13,14-secoestra-1,3,5(10)triene was determined by X-ray analysis. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.steroids.2004.04.009

文献信息

• 14(15)-unsaturated 15- and/or 16-substituted androgens with mixed androgen-progrestational profile
  申请人：——

  公开号：US20040059140A1

  公开（公告）日：2004-03-25

  Disclosed are androgen-related steroids having a &Dgr;14 double bond and carrying a substituent at either or both of the carbon atoms nos. 15 and 16. The present steroids are characterized by possessing a mixed profile of androgenic and progestagenic activities. This makes these compounds suitable for male or female hormone replacement therapy, as well as male contraception.

  本发明涉及具有&Dgr;14双键并在碳原子15和16号中的一个或两个上携带取代基的雄激素相关类固醇。这些类固醇的特点是具有雄激素和孕激素活性的混合剖面。这使得这些化合物适用于男性或女性激素替代疗法，以及男性避孕。
• Selective synthesis of 14-dehydroestranes
  作者：Gary H. Rasmusson、Glen E. Arth

  DOI：10.1016/0039-128x(73)90075-5

  日期：1973.7
• 14(15)-UNSATURATED 15- AND/OR 16- SUBSTITUTED ANDROGENS WITH MIXED ANDROGEN-PROGESTATIONAL PROFILE
  申请人：Akzo Nobel N.V.

  公开号：EP1343804A1

  公开（公告）日：2003-09-17
• [EN] 14(15)-UNSATURATED 15- AND/OR 16- SUBSTITUTED ANDROGENS WITH MIXED ANDROGEN-PROGESTATIONAL PROFILE<br/>[FR] ANDROGENES SUBSTITUES EN 15 ET/OU 16 INSATURES EN 14 (15) A PROFIL MIXTE D'ACTIVITE D'ANDROGENE-PROGESTATION
  申请人：AKZO NOBEL NV

  公开号：WO2002048169A1

  公开（公告）日：2002-06-20

  Disclosed are androgen-related steroids having a Δ14 double bond and carrying a substituent at either or both of the carbon atoms nos. 15 and 16. The present steroids are characterized by possessing a mixed profile of androgenic and progestagenic activities. This makes these compounds suitable for male or female hormone replacement therapy, as well as male contraception.
• The synthesis of functionalized 13,14-seco-steroids via Grob fragmentation
  作者：Vladimir A Khripach、Vladimir N Zhabinskii、Galina P Fando、Alla I Kuchto、Alexander S Lyakhov、Alla A Govorova、Marinus B Groen、Jaap van der Louw、Aede de Groot

  DOI：10.1016/j.steroids.2004.04.009

  日期：2004.7

  A synthetic methodology for the synthesis of 13,14-seco-steroids with substituents at C-14 and C-17 is described. The approach involves Grob fragmentation of 14beta-hydroxy-17beta-tosylates, hydroboration-oxidation of the intermediate Delta(13(17))-olefin, and hydride reduction of the 14-ketone. An unambiguous structural assignment of (13R,14S,17S)-14,17-diacetoxy-3-methoxy-7alpha-methyl-13,14-secoestra-1,3,5(10)triene was determined by X-ray analysis. (C) 2004 Elsevier B.V. All rights reserved.