jatrophadiketone | 1357352-91-0

• 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: jatrophadiketone
• 英文别名: (4aR,4bR,8S,8aR,10aS)-10a-hydroxy-3,10-dimethyl-5-methylidene-8-prop-1-en-2-yl-4a,4b,6,7,8,8a-hexahydrophenanthrene-1,4-dione
• CAS: 1357352-91-0
• 化学式: C₂₀H₂₄O₃
• 分子量: 312.409
• InChiKey: DXRLKDVUUVHSLL-RLPRXVRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  jatrophadiketone 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以95%的产率得到5-O-acetyljatrophadiketone
  参考文献：
  名称：

  Three new diterpenes from Jatropha curcas

  摘要：

  Jatrophalactone (1) and jatrophalone (2), together with jatrophadiketone (3), a 6/6/6 tricyclic diterpene transformed from rhamnofolane skeleton, have been isolated from the methanolic extract of Jatropha curcas. The structures were established on the basis of extensive spectroscopic methods and further confirmed by X-ray crystallographic analysis. The cytotoxicity against selected cell lines was evaluated. Among them, compound 1 displayed cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW480 cell lines with IC50 values of 8.5, 20.6, 19.7, 20.1, and 19.2 mu M, respectively. The possible biosynthetic pathways for 1 and 3 are proposed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.006