Acetic acid (4aS,4bR,8aS,9R,10aS)-4b,8,8,10a-tetramethyl-2-((R)-4-methyl-2,5-dioxo-cyclohex-3-enyl)-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-phenanthren-9-yl ester | 169477-50-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (4aS,4bR,8aS,9R,10aS)-4b,8,8,10a-tetramethyl-2-((R)-4-methyl-2,5-dioxo-cyclohex-3-enyl)-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-phenanthren-9-yl ester
• 英文别名: [(4aS,4bR,8aS,9R,10aS)-4b,8,8,10a-tetramethyl-2-[(1R)-4-methyl-2,5-dioxocyclohex-3-en-1-yl]-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-9-yl] acetate
• CAS: 169477-50-3
• 化学式: C₂₇H₃₈O₄
• 分子量: 426.596
• InChiKey: IBALXIBJVMUSQI-VAIOSVBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Acetic acid (4aS,4bR,8aS,9R,10aS)-4b,8,8,10a-tetramethyl-2-((R)-4-methyl-2,5-dioxo-cyclohex-3-enyl)-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-phenanthren-9-yl ester 在 盐酸 、 三甲基氯硅烷 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 生成 Suberiquinol
  参考文献：
  名称：

  Suberitenones A and B: Sesterterpenoids of an unprecedented skeletal class from the Antarctic sponge Suberites sp.

  摘要：

  Suberitenones A (1) and B (2), sesterterpenoids of an unprecedented skeletal class, have been isolated from the Antarctic sponge Suberites sp. Structures of these compounds have been determined by combined spectral and chemical studies. Absolute stereochemistry has been assigned on the basis of a combination of the Kusumi and Kakisawa modification of Mosher's method and CD measurement, Suberitenone B inhibited the cholesteryl ester transfer protein (CETP), which mediates the transfer of cholesteryl ester and triglyceride between high-density lipoproteins and low-density lipoproteins, In addition, suberitenone A has been chemically transformed to suberiquinol (10), a hydroquinone derivative.

  DOI：

  10.1021/jo00128a034
• 作为产物：
  描述：

  suberitenone B 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以78%的产率得到Acetic acid (4aS,4bR,8aS,9R,10aS)-4b,8,8,10a-tetramethyl-2-((R)-4-methyl-2,5-dioxo-cyclohex-3-enyl)-3,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-phenanthren-9-yl ester
  参考文献：
  名称：

  Suberitenones A and B: Sesterterpenoids of an unprecedented skeletal class from the Antarctic sponge Suberites sp.

  摘要：

  Suberitenones A (1) and B (2), sesterterpenoids of an unprecedented skeletal class, have been isolated from the Antarctic sponge Suberites sp. Structures of these compounds have been determined by combined spectral and chemical studies. Absolute stereochemistry has been assigned on the basis of a combination of the Kusumi and Kakisawa modification of Mosher's method and CD measurement, Suberitenone B inhibited the cholesteryl ester transfer protein (CETP), which mediates the transfer of cholesteryl ester and triglyceride between high-density lipoproteins and low-density lipoproteins, In addition, suberitenone A has been chemically transformed to suberiquinol (10), a hydroquinone derivative.

  DOI：

  10.1021/jo00128a034