N-[2-(trimethylsilyl)ethanesulfonyl]-11α,12α-aziridino-5β-H-pregnane-3,20-dione | 294628-91-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: N-[2-(trimethylsilyl)ethanesulfonyl]-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-(2-trimethylsilylethylsulfonyl)-3-azapentacyclo[8.8.0.02,4.05,9.013,18]octadecan-15-one
• CAS: 294628-91-4
• 化学式: C₂₆H₄₃NO₄SSi
• 分子量: 493.783
• InChiKey: WJGBFKHOTYFMTJ-UJUUHPHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  79.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[2-(trimethylsilyl)ethanesulfonyl]-11α,12α-aziridino-5β-H-pregnane-3,20-dione 在 吡啶 、 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 24.25h， 生成 [(1S,2S,4R,5S,6S,9S,10S,13R,15R,18S)-6-(1-acetyloxyethyl)-5,18-dimethyl-3-(2-trimethylsilylethylsulfonyl)-3-azapentacyclo[8.8.0.02,4.05,9.013,18]octadecan-15-yl] acetate
  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
• 作为产物：
  描述：

  17-乙酰基-10,13-二甲基-1,2,4,5,6,7,8,9,14,15,16,17-十二氢环戊烯并[a]菲-3-酮 、 2-(trimethylsilyl)-N-(phenyl-λ³-iodanylidene)-ethanesulfonamide 在 4 A molecular sieve 、 三氟甲烷磺酸亚铜(I)苯联合体 (2:1) 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以53%的产率得到N-[2-(trimethylsilyl)ethanesulfonyl]-11α,12α-aziridino-5β-H-pregnane-3,20-dione
  参考文献：
  名称：

  Synthesis of Aziridinosteroids

  摘要：

  使用不同的亚氨基苯基碘和氯胺氮丙啶化试剂从 5β-H-11-孕烯-3,20-二酮 (1) 制备 11α,12α-氮丙啶类固醇 (2a, b, c)。

  DOI：

  10.3390/50300443

文献信息

• PhINSes mediated aziridination of 11-pregnane derivatives: synthesis of an 11,12-aziridino analogue of neuroactive steroids
  作者：Pablo H Di Chenna、Philippe Dauban、Alberto Ghini、Ricardo Baggio、Maria Teresa Garland、Gerardo Burton、Robert H Dodd

  DOI：10.1016/s0040-4020(02)01655-1

  日期：2003.2

  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.