3,11β-dihydroxy-7α-methylestra-1,3,5(10)-trien-17-one 3-acetate 11-nitrate ester | 108887-23-6

• 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: 3,11β-dihydroxy-7α-methylestra-1,3,5(10)-trien-17-one 3-acetate 11-nitrate ester
• 英文别名: [(7R,8S,9S,11S,13S,14S)-7,13-dimethyl-11-nitrooxy-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 108887-23-6
• 化学式: C₂₁H₂₅NO₆
• 分子量: 387.433
• InChiKey: PASMNHLMENOGAM-OPYWHCCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,11β-dihydroxy-7α-methylestra-1,3,5(10)-trien-17-one 3-acetate 11-nitrate ester 生成 (+)-3,11β,17β-Trihydroxy-7α-methylestra-1,3,5(10)-triene 11-Nitrate Ester
  参考文献：
  名称：

  CROWE, DAVID E.;TANABE, MASATO;PETERS, RICHARD

  摘要：

  DOI：
• 作为产物：
  描述：

  3,9α,11β-trihydroxy-7α-methylestra-1,3,5(10)-trien-17-one 3-acetate 11-nitrate ester 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以5.75 g的产率得到3,11β-dihydroxy-7α-methylestra-1,3,5(10)-trien-17-one 3-acetate 11-nitrate ester
  参考文献：
  名称：

  11.beta.-Nitrate estrane analogs: potent estrogens

  摘要：

  Various estrane derivatives 1 reacted with cerium ammonium nitrate (CAN) selectively and efficiently to provide 9 alpha,11 beta-defunctionalized derivatives 2, which were subsequently deoxygenated at C-9 with triethylsilane/boron trifluoride etherate to the desired target 11 beta-nitratoestranes 3a, 3b, and 5. When examined for estrogenic and postcoital antifertility activity, 11 beta-nitrates 2c, 2d, and 3b most notably displayed more potent oral activity than did ethynylestradiol.

  DOI：

  10.1021/jm00130a014

文献信息

• PETERS, RICHARD H.;CROWE, DAVID F.;AVERY, MITCHELL A.;CHONG, WESLEY K. M.+, J. MED. CHEM., 32,(1989) N0, C. 2306-2310
  作者：PETERS, RICHARD H.、CROWE, DAVID F.、AVERY, MITCHELL A.、CHONG, WESLEY K. M.+

  DOI：——

  日期：——
• CROWE, DAVID E.;TANABE, MASATO;PETERS, RICHARD
  作者：CROWE, DAVID E.、TANABE, MASATO、PETERS, RICHARD

  DOI：——

  日期：——
• CROWE, DAVID F.;TANABE, MASATO;PETERS, RICHARD
  作者：CROWE, DAVID F.、TANABE, MASATO、PETERS, RICHARD

  DOI：——

  日期：——
• 11.beta.-Nitrate estrane analogs: potent estrogens
  作者：Richard H. Peters、David F. Crowe、Mitchell A. Avery、Wesley K. M. Chong、Masato Tanabe

  DOI：10.1021/jm00130a014

  日期：1989.10

  Various estrane derivatives 1 reacted with cerium ammonium nitrate (CAN) selectively and efficiently to provide 9 alpha,11 beta-defunctionalized derivatives 2, which were subsequently deoxygenated at C-9 with triethylsilane/boron trifluoride etherate to the desired target 11 beta-nitratoestranes 3a, 3b, and 5. When examined for estrogenic and postcoital antifertility activity, 11 beta-nitrates 2c, 2d, and 3b most notably displayed more potent oral activity than did ethynylestradiol.