11α,12α-aziridino-5β-H-pregnane-3,20-dione | 304641-95-0

• 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: 11α,12α-aziridino-5β-H-pregnane-3,20-dione
• 英文别名: (1S,2S,4R,5S,6S,9S,10S,13R,18S)-6-acetyl-5,18-dimethyl-3-azapentacyclo[8.8.0.02,4.05,9.013,18]octadecan-15-one
• CAS: 304641-95-0
• 化学式: C₂₁H₃₁NO₂
• 分子量: 329.483
• InChiKey: SPNPCXQNTVITQO-UICWUCEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  56.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  11α,12α-aziridino-5β-H-pregnane-3,20-dione 、 碘甲烷 在 potassium carbonate 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 18.0h， 以60%的产率得到N-methyl-11α,12α-aziridino-5β-H-pregnane-3,20-dione
  参考文献：
  名称：

  PhINSes mediated aziridination of 11-pregnane derivatives: synthesis of an 11,12-aziridino analogue of neuroactive steroids

  摘要：

  Reaction of 11-pregnene-3,20-dione (6) or 3-alpha-acetoxy-11-pregnen-20-one (12) with trimethylsilylethanesulfonyl ('Ses') iminoiodinane 5 in the presence of copper (I) triflate gave the corresponding alpha,alpha-11,12-aziridino steroids 7 and 13 in 53 and 45% yields, respectively. The Ses group of each compound was removed using the TASF reagent and the resulting free aziridine NH was methylated to afford the 11alpha,12alpha-N-methyl aziridinosteroids 9 and 15, respectively. The latter is a conformationally constrained analogue of the endogenous neurosteroid pregnanolone (1). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01655-1
• 作为产物：
  描述：

  N-[2-(trimethylsilyl)ethanesulfonyl]-11α,12α-aziridino-5β-H-pregnane-3,20-dione 在 三(二甲氨基)锍二氟三甲基硅酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 以77%的产率得到11α,12α-aziridino-5β-H-pregnane-3,20-dione
  参考文献：
  名称：

  Aziridination of 11-pregnene-3,20-dione using PhIN-Ses

  摘要：

  The copper-catalyzed reaction of [N-(Ses)imino]phenyliodinane with 11-pregnene-3,20-dione gave the corresponding aziridine in 53% yield. The Ses protecting group could be conveniently removed using the TASF reagent. Furthermore, nucleophilic ring opening of the protected N-Ses-aziridine with thiophenol in the presence of a Lewis acid led to introduction of the thiophenol group at the alpha-12 position but, unexpectedly, concomitant loss of the Ses group to provide compound 10. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01228-4