4-((3R,3aS,3bR,5R,5aS,6aS,9aR,10aR,10bS,12aS)-5-ethyl-5-(2-hydroxyethoxy)-1-((S)-1-hydroxypropan-2-yl)-8,8,10a,12a-tetramethyl-3a,3b,4,5,5a,6,6a,9a,10,10a,10b,11,12,12a-tetradecahydro-3H-cyclopenta[7,8]phenanthro[2,3-d][1,3]dioxol-3-yl)butyl benzoate | 1353113-40-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-((3R,3aS,3bR,5R,5aS,6aS,9aR,10aR,10bS,12aS)-5-ethyl-5-(2-hydroxyethoxy)-1-((S)-1-hydroxypropan-2-yl)-8,8,10a,12a-tetramethyl-3a,3b,4,5,5a,6,6a,9a,10,10a,10b,11,12,12a-tetradecahydro-3H-cyclopenta[7,8]phenanthro[2,3-d][1,3]dioxol-3-yl)butyl benzoate
• CAS: 1353113-40-2
• 化学式: C₄₀H₆₀O₇
• 分子量: 652.912
• InChiKey: KDSRIFSTERSMPL-IQRWOHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.34
• 重原子数：
  47.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  94.45
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-((3R,3aS,3bR,5R,5aS,6aS,9aR,10aR,10bS,12aS)-5-ethyl-5-(2-hydroxyethoxy)-1-((S)-1-hydroxypropan-2-yl)-8,8,10a,12a-tetramethyl-3a,3b,4,5,5a,6,6a,9a,10,10a,10b,11,12,12a-tetradecahydro-3H-cyclopenta[7,8]phenanthro[2,3-d][1,3]dioxol-3-yl)butyl benzoate 、 乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以60%的产率得到(6R,20S)-20-acetoxymethyl-6-(2-acetoxyethyloxy)-15β-(4-benzoyloxybutyl)-2α,3α-isopropylidendioxy-6-ethyl-5α-pregna-6-ene (XIIa)
  参考文献：
  名称：

  Steroids modified at C15. Synthesis and spectra-structure correlations

  摘要：

  A synthesis of 15-benzoyloxybutyl-20-hydroxymethylpregn-16-enes, the intermediates in the synthesis of brassino- and ecdysteroids modified in the D ring was performed starting with 2 alpha,3 alpha-isopropylidenedioxy-6,6-ethylenedyoxy-5 alpha-androst-15-ene-17-one and its 2 beta,3 beta-isomer through a sequence of reactions involving Michael addition, Wittig reaction and ene reaction. Structures of the compounds were proved by the methods of two-dimensional NMR spectroscopy.

  DOI：

  10.1134/s1070363211100185
• 作为产物：
  描述：

  2α,3α-isopropylidenedioxy-6,6-ethylenedioxy-5α-androst-15-en-17-one 在 copper(I) bromide dimethylsulfide complex 、 四丁基氟化铵 、 氯化二乙基铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 10.33h， 生成 4-((3R,3aS,3bR,5R,5aS,6aS,9aR,10aR,10bS,12aS)-5-ethyl-5-(2-hydroxyethoxy)-1-((S)-1-hydroxypropan-2-yl)-8,8,10a,12a-tetramethyl-3a,3b,4,5,5a,6,6a,9a,10,10a,10b,11,12,12a-tetradecahydro-3H-cyclopenta[7,8]phenanthro[2,3-d][1,3]dioxol-3-yl)butyl benzoate
  参考文献：
  名称：

  Steroids modified at C15. Synthesis and spectra-structure correlations

  摘要：

  A synthesis of 15-benzoyloxybutyl-20-hydroxymethylpregn-16-enes, the intermediates in the synthesis of brassino- and ecdysteroids modified in the D ring was performed starting with 2 alpha,3 alpha-isopropylidenedioxy-6,6-ethylenedyoxy-5 alpha-androst-15-ene-17-one and its 2 beta,3 beta-isomer through a sequence of reactions involving Michael addition, Wittig reaction and ene reaction. Structures of the compounds were proved by the methods of two-dimensional NMR spectroscopy.

  DOI：

  10.1134/s1070363211100185