N-<3,17-bis<(trimethylsilyl)oxy>androsta-2,4,16-trien-19-yl>-2,2,2-trifluoro-N-<(2-methoxyethoxy)methyl>acetamide | 143033-65-2

• 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: N-<3,17-bis<(trimethylsilyl)oxy>androsta-2,4,16-trien-19-yl>-2,2,2-trifluoro-N-<(2-methoxyethoxy)methyl>acetamide
• 英文别名: 19-[N-[(2-methoxyethoxy)-methyl]trifluoroacetamido]-3,17-bis(trimethylsilyloxy)androsta-2,4,16-triene；2,2,2-trifluoro-N-(2-methoxyethoxymethyl)-N-[[(8R,9S,10S,13S,14S)-13-methyl-3,17-bis(trimethylsilyloxy)-6,7,8,9,11,12,14,15-octahydro-1H-cyclopenta[a]phenanthren-10-yl]methyl]acetamide
• CAS: 143033-65-2
• 化学式: C₃₁H₅₀F₃NO₅Si₂
• 分子量: 629.908
• InChiKey: GICOPMBZGCKEJF-XTOYTDESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.63
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-<3,17-bis<(trimethylsilyl)oxy>androsta-2,4,16-trien-19-yl>-2,2,2-trifluoro-N-<(2-methoxyethoxy)methyl>acetamide 在 四氯化钛 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (4α,10α)-2-aza-4,19-cyclo-A-dihomoandrost-4b-ene-4a,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：

  19-<(trifluoroacetyl)amino>-4-androstene-3,17-dione 在 18-冠醚-6 、 potassium hydride 、 lithium diisopropyl amide 作用下， 反应 26.55h， 生成 N-<3,17-bis<(trimethylsilyl)oxy>androsta-2,4,16-trien-19-yl>-2,2,2-trifluoro-N-<(2-methoxyethoxy)methyl>acetamide
  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-methyleneamino bridged steroids as aromatase inhibitors
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US05126488A1

  公开（公告）日：1992-06-30

  The present invention is directed to 2.beta.,19-(methyleneamino)androst-4-ene-3,17-dione which has the formula ##STR1## and the corresponding 17.beta.-ol which are useful as aromatase inhibitors. The compounds are prepared by the cyclization of an appropriate 19-[N-protected-[(2-methoxyethoxy)methylamino] steroid using titanium tetrachloride followed by, if desired, selective reduction of the 17-ketone.

  本发明涉及具有以下式子的2.beta.,19-(亚甲基氨基)雄甾-4-烯-3,17-二酮及其对应的17.beta.-醇，其可用作芳香化酶抑制剂。该化合物通过使用四氯化钛催化适当的19-[N-保护-[(2-甲氧基乙氧基)甲基]氨基]类固醇环化制备，然后，如果需要，选择性还原17-酮基。
• 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.