(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Tris-allyloxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester | 756483-00-8

• 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: (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Tris-allyloxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester
• CAS: 756483-00-8
• 化学式: C₃₄H₅₄O₅
• 分子量: 542.8
• InChiKey: PCJGPPDEPRPQTD-ISMULCGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.17
• 重原子数：
  39.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Tris-allyloxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-10,13-Dimethyl-3,7,12-tris-oxiranylmethoxy-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester
  参考文献：
  名称：

  Environmentally Responsive Molecular Baskets:  Unimolecular Mimics of Both Micelles and Reversed Micelles

  摘要：

  When four facially amphiphilic cholate derivatives are attached to a tetraaminocalixarene scaffold, the resulting molecule responds to environmental changes by rotation of the cholate units. In polar solvents, the molecule adopts a micellelike conformation with the hydrophilic alpha-faces of the cholates pointing outward. In nonpolar solvents, it turns inside out, assuming a reversed micellelike conformation with the hydrophobic beta-faces pointing outward. Switching between the two conformations is driven by solvophobic interactions and is fully reversible.

  DOI：

  10.1021/ol048679p
• 作为产物：
  描述：

  胆酸 在 硫酸 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 生成 (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Tris-allyloxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester
  参考文献：
  名称：

  Environmentally Responsive Molecular Baskets:  Unimolecular Mimics of Both Micelles and Reversed Micelles

  摘要：

  When four facially amphiphilic cholate derivatives are attached to a tetraaminocalixarene scaffold, the resulting molecule responds to environmental changes by rotation of the cholate units. In polar solvents, the molecule adopts a micellelike conformation with the hydrophilic alpha-faces of the cholates pointing outward. In nonpolar solvents, it turns inside out, assuming a reversed micellelike conformation with the hydrophobic beta-faces pointing outward. Switching between the two conformations is driven by solvophobic interactions and is fully reversible.

  DOI：

  10.1021/ol048679p