3β-acetoxy-16α-hydroxy-23,24-dinor-5α,17βH-cholan-22-oic acid-lactone | 216572-43-9

• 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: 3β-acetoxy-16α-hydroxy-23,24-dinor-5α,17βH-cholan-22-oic acid-lactone
• 英文别名: 3β-Acetoxy-16α-hydroxy-23,24-dinor-5α,17βH-cholan-22-saeure-lacton；[(1R,2S,4R,7S,8S,9S,12S,13S,16S,18S)-7,9,13-trimethyl-6-oxo-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosan-16-yl] acetate
• CAS: 216572-43-9
• 化学式: C₂₄H₃₆O₄
• 分子量: 388.547
• InChiKey: HUESGZPZXJYYMK-FRVHHDRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  28.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-16α-hydroxy-23,24-dinor-5α,17βH-cholan-22-oic acid-lactone 在 chromium(VI) oxide 、 氢氧化钾 、 lithium aluminium tetrahydride 作用下， 生成 3,16-dioxo-23,24-dinor-5α-cholan-22-oic acid methyl ester
  参考文献：
  名称：

  The Synthesis of the Steroidal Sapogenins^1,2

  摘要：

  DOI：

  10.1021/ja01507a028
• 作为产物：
  描述：

  tert-butyl 2-[(3S,8R,9S,10R,13S,14S,16S,17R)-3,16-diacetyloxy-17-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl]propanoate 在 palladium on activated charcoal 盐酸 、 氢气 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 乙酸乙酯 、 甲苯 为溶剂， 反应 0.5h， 生成 3β-acetoxy-16α-hydroxy-23,24-dinor-5α,17βH-cholan-22-oic acid-lactone
  参考文献：
  名称：

  Mechanistic studies of the rearrangements of steroidal 16,17-ketols and syntheses of 20→16-cis-γ-carbolactones

  摘要：

  Utilization of 17-keto-androstanes as starting materials for the synthesis of alpha- or beta-oriented steroidal 20-->16-gamma-carbolactones has been explored following two different strategies. A highly efficient, stereospecific protocol has been developed for the beta-oriented cis-gamma-lactone. A different approach, involving prior attachment of a 3-carbon side chain on C-17 of a 17-oxo-16 beta-acetoxyandrostane led to the epimeric, cc-oriented lactone. The mechanism of the rearrangement of epimeric 16 beta- or 16 alpha-hydroxy-17-ketoandrostanes to 17 beta-hydroxy-16-keto-androstanes was studied by C-13 NMR spectroscopy. The former occurs through a 1,2-sigmatropic H-shift, while the latter is likely to take place by simple enolization-reprotonation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00042-5

文献信息

• Stereospecific Synthesis of Steroidal 20,16-γ-Carbolactones
  作者：Andrea C. Bruttomesso、Darío Doller、Eduardo G Gros

  DOI：10.1080/00397919808004965

  日期：1998.11

  Abstract Two strategies have been explored for the synthesis of steroidal 20,16-γ-carbolactones from the corresponding 17-ketoandrostane. A highly efficient, stereospecific protocol has been developed for the β-oriented cis-γ-lactone, based on a Michael addition of cyanide to a conjugated ketone. A different approach, involving prior attachment of a 3-carbon side chain on C-17 of a 17-oxo-16β-acetoxy-androstane

  摘要 已经探索了从相应的 17-酮雄甾烷合成甾体 20,16-γ-碳内酯的两种策略。基于氰化物与共轭酮的迈克尔加成，已经为 β 取向的顺式-γ-内酯开发了一种高效的立体特异性方案。一种不同的方法，包括在 17-oxo-16β-乙酰氧基-雄烷的 C-17 上预先连接 3-碳侧链，导致差向异构、α 取向的内酯。
• Danieli et al., Chemistry and industry, 1958, p. 1724
  作者：Danieli et al.

  DOI：——

  日期：——
• Danieli et al., Chemistry and industry, 1958, p. 1725
  作者：Danieli et al.

  DOI：——

  日期：——