(1S,2S,6S,12S,14R)-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradec-9-en-4-one | 157751-04-7

• 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: (1S,2S,6S,12S,14R)-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradec-9-en-4-one
• CAS: 157751-04-7
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: QXJYIGSXUBOSID-CLPVKGIJSA-N

物化性质

• 沸点：
  406.5±45.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  parthenolide 在 吡啶 、 对甲苯磺酸 、 间氯过氧苯甲酸 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 59.0h， 生成 Mesatlantin C, CAS#137624-14-7, 天然产物Mesatlantin C 、 (1S,2S,6S,12S,14R)-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradec-9-en-4-one 、 小白菊
  参考文献：
  名称：

  Biomimetic Semisynthesis of Arglabin from Parthenolide

  摘要：

  The semisynthesis of arglabin, an anticancer drug in clinical application, is developed from abundant natural product parthenolide via three steps. Each step in this sequence is highly stereoselective, and the substrate-dependent stereoselectivity in the epoxidation step can be explained by computational calculations. The success of chemical semisynthesis of arglabin suggests that the biosynthesis of arglabin might proceed in a similar pathway.

  DOI：

  10.1021/jo300888s

文献信息

• Biomimetic Semisynthesis of Arglabin from Parthenolide
  作者：Jia-Dai Zhai、Dongmei Li、Jing Long、Hao-Liang Zhang、Jian-Ping Lin、Chuan-Jiang Qiu、Quan Zhang、Yue Chen

  DOI：10.1021/jo300888s

  日期：2012.8.17

  The semisynthesis of arglabin, an anticancer drug in clinical application, is developed from abundant natural product parthenolide via three steps. Each step in this sequence is highly stereoselective, and the substrate-dependent stereoselectivity in the epoxidation step can be explained by computational calculations. The success of chemical semisynthesis of arglabin suggests that the biosynthesis of arglabin might proceed in a similar pathway.