7-aza-5α-pregnane-3,20-dione | 958867-01-1

• 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: 7-aza-5α-pregnane-3,20-dione
• 英文别名: (1S,3aR,3bR,5aS,9aS,9bR,11aS)-1-acetyl-9a,11a-dimethyl-1,2,3,3a,3b,4,5,5a,6,8,9,9b,10,11-tetradecahydrocyclopenta[c]phenanthridin-7-one
• CAS: 958867-01-1
• 化学式: C₂₀H₃₁NO₂
• 分子量: 317.472
• InChiKey: ULDANPIEGNQIGC-WVSUQSNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-aza-5α-pregnane-3,20-dione 在 hydrogen hexachloroiridate(IV) hydrate 次磷酸 作用下， 以 水 、 异丙醇 为溶剂， 反应 7.0h， 以75%的产率得到7-aza-allopregnanolone
  参考文献：
  名称：

  Neurosteroids: 7-aza-allopregnanolone—a poor substitute for allopregnanolone

  摘要：

  7-Nor-20-oxopregn-5-en-3 beta-yl acetate was converted into (20R)-5 beta,6 beta-epoxy-7-nor-5 beta-pregnane-3 beta,20-diyl diacetate in three steps. Stereospecific migration of the 6 alpha-hydride ion led to a 6-oxo derivative with a 5 alpha-configuration. The (Z)- oxime of this ketone underwent Beckmann rearrangement to yield a lactam with the nitrogen in position 7. Lithium aluminium hydride reduction yielded the dihydroxy amine, which was either oxidised or Boc-protected and then oxidised to 7-aza-5 alpha-pregnane-3,20-dione. Its regioselective reduction produced 7-aza-3 alpha- hydroxy-5 alpha-pregnan-20-one-a poor inhibitor for the binding of [S-35] TBPS to the GABA(A) receptor. The corresponding lactam-7-aza3 alpha- hydroxy-5 alpha-pregnane-6,20-dione-was inactive. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.078
• 作为产物：
  描述：

  7-aza-3β-hydroxy-5α-pregnan-20-one 生成 7-aza-5α-pregnane-3,20-dione
  参考文献：
  名称：

  Neurosteroids: 7-aza-allopregnanolone—a poor substitute for allopregnanolone

  摘要：

  7-Nor-20-oxopregn-5-en-3 beta-yl acetate was converted into (20R)-5 beta,6 beta-epoxy-7-nor-5 beta-pregnane-3 beta,20-diyl diacetate in three steps. Stereospecific migration of the 6 alpha-hydride ion led to a 6-oxo derivative with a 5 alpha-configuration. The (Z)- oxime of this ketone underwent Beckmann rearrangement to yield a lactam with the nitrogen in position 7. Lithium aluminium hydride reduction yielded the dihydroxy amine, which was either oxidised or Boc-protected and then oxidised to 7-aza-5 alpha-pregnane-3,20-dione. Its regioselective reduction produced 7-aza-3 alpha- hydroxy-5 alpha-pregnan-20-one-a poor inhibitor for the binding of [S-35] TBPS to the GABA(A) receptor. The corresponding lactam-7-aza3 alpha- hydroxy-5 alpha-pregnane-6,20-dione-was inactive. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.078

文献信息

• Neurosteroids: 7-aza-allopregnanolone—a poor substitute for allopregnanolone
  作者：Alexander Kasal、Zdena Krištofíková、Miloš Buděšínský

  DOI：10.1016/j.tet.2007.08.078

  日期：2007.11

  7-Nor-20-oxopregn-5-en-3 beta-yl acetate was converted into (20R)-5 beta,6 beta-epoxy-7-nor-5 beta-pregnane-3 beta,20-diyl diacetate in three steps. Stereospecific migration of the 6 alpha-hydride ion led to a 6-oxo derivative with a 5 alpha-configuration. The (Z)- oxime of this ketone underwent Beckmann rearrangement to yield a lactam with the nitrogen in position 7. Lithium aluminium hydride reduction yielded the dihydroxy amine, which was either oxidised or Boc-protected and then oxidised to 7-aza-5 alpha-pregnane-3,20-dione. Its regioselective reduction produced 7-aza-3 alpha- hydroxy-5 alpha-pregnan-20-one-a poor inhibitor for the binding of [S-35] TBPS to the GABA(A) receptor. The corresponding lactam-7-aza3 alpha- hydroxy-5 alpha-pregnane-6,20-dione-was inactive. (C) 2007 Elsevier Ltd. All rights reserved.