4α,14α-Dimethyl-5α-cholest-9(11)-ene-3,7-dione | 173690-88-5

• 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: 4α,14α-Dimethyl-5α-cholest-9(11)-ene-3,7-dione
• 英文别名: (4S,5S,8S,10S,13R,14S,17R)-4,10,13,14-tetramethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,4,5,6,8,12,15,16,17-decahydrocyclopenta[a]phenanthrene-3,7-dione
• CAS: 173690-88-5
• 化学式: C₂₉H₄₆O₂
• 分子量: 426.683
• InChiKey: RCKWTKDGAYHKLU-HPLIBHEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4α,14α-Dimethyl-5α-cholest-9(11)-ene-3,7-dione 在 吡啶 、 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 62.0h， 生成 3,7-Dioxo-31-nor-5α-cucurbit-1-en-11β-yl acetate
  参考文献：
  名称：

  Tetracyclic triterpenes. Part 16. Synthesis of 31-norcucurbitane and fusidane derivatives in the skeletal rearrangements of 9,11-epoxy-4β-demethyl-5α-lanostanes

  摘要：

  The BF3 . Et(2)O-catalysed rearrangement of 9 beta,11 beta-epoxy-4 beta-demethyl-5 alpha-lanostan-7-one derivatives 11 and 12 in acetic anhydride resulted in formation of 19(10-->9 beta)abeo compounds (31-norcucurbitanes) 20-22 or 23 and 24, respectively. The extent of a rearrangement was dependent on the substituent at position 3 of the steroid. Reaction of the 9 alpha,11 alpha-epoxide 17 under similar conditions gave fusidenone 25 (31-norprotostane) in high yield which had the carbon skeleton characteristic of the steroidal antibiotic, fusidic acid.

  DOI：

  10.1039/p19960000201
• 作为产物：
  描述：

  oxo-3 dimethyl-4α,14α cholesta-5α ene-8 在 吡啶 、 chromium(VI) oxide 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 氯仿 、 溶剂黄146 为溶剂， 反应 2.0h， 生成 4α,14α-Dimethyl-5α-cholest-9(11)-ene-3,7-dione
  参考文献：
  名称：

  Tetracyclic triterpenes. Part 16. Synthesis of 31-norcucurbitane and fusidane derivatives in the skeletal rearrangements of 9,11-epoxy-4β-demethyl-5α-lanostanes

  摘要：

  The BF3 . Et(2)O-catalysed rearrangement of 9 beta,11 beta-epoxy-4 beta-demethyl-5 alpha-lanostan-7-one derivatives 11 and 12 in acetic anhydride resulted in formation of 19(10-->9 beta)abeo compounds (31-norcucurbitanes) 20-22 or 23 and 24, respectively. The extent of a rearrangement was dependent on the substituent at position 3 of the steroid. Reaction of the 9 alpha,11 alpha-epoxide 17 under similar conditions gave fusidenone 25 (31-norprotostane) in high yield which had the carbon skeleton characteristic of the steroidal antibiotic, fusidic acid.

  DOI：

  10.1039/p19960000201

文献信息

• Tetracyclic triterpenes. Part 16. Synthesis of 31-norcucurbitane and fusidane derivatives in the skeletal rearrangements of 9,11-epoxy-4β-demethyl-5α-lanostanes
  作者：Zdzisław Paryzek、Jacek Martynow

  DOI：10.1039/p19960000201

  日期：——

  The BF3 . Et(2)O-catalysed rearrangement of 9 beta,11 beta-epoxy-4 beta-demethyl-5 alpha-lanostan-7-one derivatives 11 and 12 in acetic anhydride resulted in formation of 19(10-->9 beta)abeo compounds (31-norcucurbitanes) 20-22 or 23 and 24, respectively. The extent of a rearrangement was dependent on the substituent at position 3 of the steroid. Reaction of the 9 alpha,11 alpha-epoxide 17 under similar conditions gave fusidenone 25 (31-norprotostane) in high yield which had the carbon skeleton characteristic of the steroidal antibiotic, fusidic acid.