3α-acetoxy-5β-H-11-pregnen-20-one | 526203-68-9

• 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: 3α-acetoxy-5β-H-11-pregnen-20-one
• 英文别名: 3α-acetoxy-5β-pregn-11-en-20-one；3α-Acetoxy-5β-pregn-11-en-20-on；[(3R,5R,8S,9S,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-2,3,4,5,6,7,8,9,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 526203-68-9
• 化学式: C₂₃H₃₄O₃
• 分子量: 358.521
• InChiKey: KCAUMDZVEARSJW-LEQCJQSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3α-acetoxy-5β-H-11-pregnen-20-one 在 4 A molecular sieve 、 三(二甲氨基)锍二氟三甲基硅酸 、 三氟甲烷磺酸亚铜(I)苯联合体 (2:1) 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 30.75h， 生成 [(1S,2S,4R,5S,6S,9S,10S,13R,15R,18S)-6-acetyl-3,5,18-trimethyl-3-azapentacyclo[8.8.0.02,4.05,9.013,18]octadecan-15-yl] acetate
  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：

  12α-hydroxy-3α-acetoxy-5β-pregnanone-(20) 在 吡啶 、 2,3,5-三甲基吡啶 作用下， 反应 150.0h， 生成 3α-acetoxy-5β-H-11-pregnen-20-one
  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

文献信息

• �ber Bestandteile der Nebennierenrinde und verwandte Stoffe. 68. Mitteilung. Pregnandiol-(3 ?, 11 ?)-on-(20) und Pregnandiol-(3 ?, 11 ?)-on-(20)
  作者：J. von Euw、A. Lardon、T. Reichstein

  DOI：10.1002/hlca.194402701107

  日期：——