3β-hydroxy-allopregn-9(11)-en-20-one 3-acetate | 6618-29-7

• 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: 3β-hydroxy-allopregn-9(11)-en-20-one 3-acetate
• 英文别名: 3β-acetoxy-5α-pregn-9(11)-en-20-one；3β-Acetoxy-5α-pregn-9(11)-en-20-on；3β-Acetoxy-5α-Δ⁹⁽¹¹⁾-pregnen-20-on；3β-Acetoxy-20-oxo-5α-pregn-9(11)-en
• CAS: 6618-29-7
• 化学式: C₂₃H₃₄O₃
• 分子量: 358.521
• InChiKey: RWGWCMSZRIAUME-SZKCUPFNSA-N

物化性质

• 熔点：
  125-126 °C
• 沸点：
  452.9±45.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3β-hydroxy-allopregn-9(11)-en-20-one 3-acetate 生成 3β,6α-dihydroxy-5α-pregn-9(11)-en-20-one
  参考文献：
  名称：

  Steroidal Sapogenins. XI. Experiments in the Hecogenin Series (Part 2)

  摘要：

  DOI：

  10.1021/jo50002a015
• 作为产物：
  描述：

  3Β-乙酰氧基孕甾-9(11),16-二烯-20-酮 在 Raney nickel 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以86%的产率得到3β-hydroxy-allopregn-9(11)-en-20-one 3-acetate
  参考文献：
  名称：

  Synthesis of cytotoxic novel 9,11-secosterol analogs: Structure/activity studies

  摘要：

  In an effort to determine the pharmaceutical utility and the structural requirements for activity against tumor cell lines, 30 novel 9,11-secosterol analogues with different side chains and degrees of oxidation at C-9 were synthesized starting from hecogenin. Evaluation of the synthesized compounds for cytotoxicity against KB, HeLa and MCF-7 cell lines revealed that some important structural features are required for activity. The presence of a cholesterol-type side chain, which appears to play a major role in determining the biological activity, the existence of a ketone functional at C-9 is also crucial for anticancer activity whereas hydroxyl/ketone function at C-22 on the side chain did not increase cytotoxicity. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.05.003

文献信息

• Hydroxy-steroids. Part IV. The preparation and spectra of steroid olefins
  作者：G. M. L. Cragg、C. W. Davey、D. N. Hall、G. D. Meakins、E. E. Richards、T. L. Whateley

  DOI：10.1039/j39660001266

  日期：——

  Convenient preparations have been developed for a series of steroidal mono-olefins free from oxygenated substituents: this Series includes representatives of all but one of the possible endocyclic olefins. The infrared, nuclear magnetic resonance, and ultraviolet spectra of the compounds were examined with particular attention to the relative power and scope of the different techniques in structural

  已经开发了一系列不含氧化取代基的甾族单烯烃的简便制剂：该系列包括所有可能的内环烯烃中的一种，但仅其中一种代表。检查了化合物的红外光谱，核磁共振光谱和紫外光谱，并特别注意了结构诊断中不同技术的相对功效和范围。
• The addition of nitrosyl fluoride to steroid 9(11)-olefins (1)
  作者：Joan P. Gratz、David Rosenthal

  DOI：10.1016/s0039-128x(69)80080-2

  日期：1969.12