(-)-3-O-acetyl-15-O-propionylcharaciol | 1160700-01-5

• 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: (-)-3-O-acetyl-15-O-propionylcharaciol
• CAS: 1160700-01-5
• 化学式: C₂₅H₃₆O₆
• 分子量: 432.557
• InChiKey: PVNLRPHTPFRTKN-LTVJXCNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  31.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  86.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (-)-3-O-acetyl-15-O-propionylcharaciol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 20.5h， 以95%的产率得到C₂₅H₃₆O₇
  参考文献：
  名称：

  Total Synthesis of Natural and Non-Natural Δ^5,6Δ^12,13-Jatrophane Diterpenes and Their Evaluation as MDR Modulators

  摘要：

  We report the details of the total synthesis of natural and non-natural jatropha-5,12-dienes. The successful tactic for the assembly of the strained trans-bicyclo[10.3.0]pentadecane scaffold employed a B-alkyl Suzuki-Miyaura cross-coupling for the formation of the C5/C6 double bond and a ring-closing metathesis for the construction of the C12/C13 double bond. The key step of the synthesis of the cyclopentane fragment, an uncatalyzed intramolecular carbonyl-ene reaction, was studied computationally by DFT calculations. The members of the ensemble of synthetic natural and non-natural jatrophanes were subsequently examined as modulators for the ABCB1, ABCG2, and ABCC1 efflux proteins, which are associated with multidrug resistance in cancer chemotherapy.

  DOI：

  10.1021/jo1019738
• 作为产物：
  描述：

  3-O-acetylcharaciol 、 丙酸酐 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以79%的产率得到(-)-3-O-acetyl-15-O-propionylcharaciol
  参考文献：
  名称：

  Total Synthesis of Jatrophane Diterpenes from Euphorbia characias

  摘要：

  The enantioselective total synthesis of the jatrophane diterpene (-)-15-O-acetyl-3-O-propionylcharaciol is described. Starting from an advanced cyclopentane building block, a B-alkyl Suzuki-Miyaura cross-coupling and carbonyl addition were utilized to assemble a fully functionalized triene, and a ring-closing metathesis was then employed to construct the rigid 12-membered ring. Twenty-five years after the original report on the isolation of the natural product, our total synthesis unambiguously corroborates the original tentative structural assignment.

  DOI：

  10.1021/ol900819u