Acetyl benzoyloxy prasterone | 307976-92-7

• 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: Acetyl benzoyloxy prasterone
• 英文别名: [(3S,7S,8R,9S,10R,13S,14S)-3-acetyloxy-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-7-yl] benzoate
• CAS: 307976-92-7
• 化学式: C₂₈H₃₄O₅
• 分子量: 450.575
• InChiKey: MEODRVPTUXZOCM-PVPHLPABSA-N

物化性质

• 熔点：
  100 °C
• 沸点：
  558.6±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)
• LogP：
  5.469 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Acetyl benzoyloxy prasterone 在 sodium hydroxide 作用下， 以81%的产率得到7-羟基去氢表雄酮
  参考文献：
  名称：

  New efficient and totally stereoselective copper allylic benzoyloxylation of sterol derivatives

  摘要：

  A new efficient and totally stereoselective copper allylic benzoyloxylation of sterol derivatives has been developed. This methodology has been successfully applied to the synthesis of 7 alpha-hydroxy DHEA and 7 alpha-hydroxy cholesterol in a two-step synthesis with high chemical yields (77% and 61% overall yield, respectively). A mechanistic rationale justifying the total stereoselectivity encountered has been proposed. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.024
• 作为产物：
  描述：

  过氧化苯甲酸叔丁酯 、 醋酸去氢表雄酮 在 copper(I) bromide 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以95%的产率得到Acetyl benzoyloxy prasterone
  参考文献：
  名称：

  New efficient and totally stereoselective copper allylic benzoyloxylation of sterol derivatives

  摘要：

  A new efficient and totally stereoselective copper allylic benzoyloxylation of sterol derivatives has been developed. This methodology has been successfully applied to the synthesis of 7 alpha-hydroxy DHEA and 7 alpha-hydroxy cholesterol in a two-step synthesis with high chemical yields (77% and 61% overall yield, respectively). A mechanistic rationale justifying the total stereoselectivity encountered has been proposed. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.024

文献信息

• New efficient and totally stereoselective copper allylic benzoyloxylation of sterol derivatives
  作者：Jean Michel Brunel、Ludovic Billottet、Yves Letourneux

  DOI：10.1016/j.tetasy.2005.08.024

  日期：2005.9

  A new efficient and totally stereoselective copper allylic benzoyloxylation of sterol derivatives has been developed. This methodology has been successfully applied to the synthesis of 7 alpha-hydroxy DHEA and 7 alpha-hydroxy cholesterol in a two-step synthesis with high chemical yields (77% and 61% overall yield, respectively). A mechanistic rationale justifying the total stereoselectivity encountered has been proposed. (C) 2005 Elsevier Ltd. All rights reserved.