10-(3-hydroxypropyl)estr-5-ene-3,17-dione cyclic bis(1,2-ethanediyl acetal) | 142645-77-0

• 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: 10-(3-hydroxypropyl)estr-5-ene-3,17-dione cyclic bis(1,2-ethanediyl acetal)
• 英文别名: 3,3,17,17-bis(ethylenedioxy)-19-(2-hydroxyethyl)androst-5-ene
• CAS: 142645-77-0
• 化学式: C₂₅H₃₈O₅
• 分子量: 418.574
• InChiKey: AZPHIIRBHJGBMN-VUBDRERZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  10-(3-hydroxypropyl)estr-5-ene-3,17-dione cyclic bis(1,2-ethanediyl acetal) 在 吡啶 、 对甲苯磺酸 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 92.0h， 生成 10-<3-<<(4-methylphenyl)sulfonyl>oxy>propyl>estr-4-ene-3,17-dione
  参考文献：
  名称：

  Synthesis of 2,19-bridged androstenediones

  摘要：

  The syntheses of 2,19-(methyleneoxy)androst-4-ene-3,17-dione (4a), a potent, time-dependent inhibitor of human placental aromatase, and its thio (4b), amino (5), and methylene (14) analogs are described. The key step in the construction of 4a, 4b, and 5 is a Lewis acid-mediated intramolecular alkylation of an A-ring O-trimethylsilyl dienol ether.

  DOI：

  10.1021/jo00045a028
• 作为产物：
  描述：

  3,17-bis(ethylenedioxy)-androst-5-en-19-al 在 正丁基锂 、 氨 、 lithium 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 25.0h， 生成 10-(3-hydroxypropyl)estr-5-ene-3,17-dione cyclic bis(1,2-ethanediyl acetal)
  参考文献：
  名称：

  Synthesis of 2,19-bridged androstenediones

  摘要：

  The syntheses of 2,19-(methyleneoxy)androst-4-ene-3,17-dione (4a), a potent, time-dependent inhibitor of human placental aromatase, and its thio (4b), amino (5), and methylene (14) analogs are described. The key step in the construction of 4a, 4b, and 5 is a Lewis acid-mediated intramolecular alkylation of an A-ring O-trimethylsilyl dienol ether.

  DOI：

  10.1021/jo00045a028

文献信息

• 2.beta.,19-ethylene bridged steroids as aromatase inhibitors
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US05166201A1

  公开（公告）日：1992-11-24

  The present invention is directed to a group of androstane compounds which contain an ethylene radical bridging the 2- and 19-positions. These compounds are useful as aromatase inhibitors and they are prepared by the cyclization of a 19-[2-(4-toluenesulfonyloxy)ethyl]androst-4-ene-3,17-dione using a strong base.

  本发明涉及一组含有乙烯基桥接2-和19-位置的雄甾烷化合物。这些化合物有用作芳香化酶抑制剂，并且它们是通过使用强碱将19-[2-(4-甲苯磺酰氧)乙基]雄甾-4-烯-3,17-二酮环化制备的。
• 2-beta,19-ethylene bridged steroids as aromatase inhibitors
  申请人：MERRELL PHARMACEUTICALS INC.

  公开号：EP0488383A1

  公开（公告）日：1992-06-03

  The present invention is directed to a group of androstane compounds which contain an ethylene radical bridging the 2- and 19-positions. These compounds are useful as aromatase inhibitors and they are prepared by the cyclization of a 19-[2-(4-toluenesulfonyloxy)ethyl]androst-4-ene-3,17-dione using a strong base.

  本发明涉及一组雄甾烷化合物，它们含有一个连接 2-位和 19-位的乙烯基。这些化合物可用作芳香化酶抑制剂，其制备方法是使用强碱使 19-[2-（4-甲苯磺酰氧基）乙基]雄甾-4-烯-3,17-二酮环化。
• US5166201A
  申请人：——

  公开号：US5166201A

  公开（公告）日：1992-11-24
• Synthesis of 2,19-bridged androstenediones
  作者：Joseph P. Burkhart、Edward W. Huber、F. Mark Laskovics、Norton P. Peet

  DOI：10.1021/jo00045a028

  日期：1992.9

  The syntheses of 2,19-(methyleneoxy)androst-4-ene-3,17-dione (4a), a potent, time-dependent inhibitor of human placental aromatase, and its thio (4b), amino (5), and methylene (14) analogs are described. The key step in the construction of 4a, 4b, and 5 is a Lewis acid-mediated intramolecular alkylation of an A-ring O-trimethylsilyl dienol ether.