(S,E)-4-(2-((1S,2S,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyloctahydro-1H-spiro[naphthalene-2,2'-oxiran]-1-yl)ethylidene)-5-oxotetrahydrofuran-3-yl 3-(3,4-dimethoxyphenyl)acrylate | 848125-91-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (S,E)-4-(2-((1S,2S,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyloctahydro-1H-spiro[naphthalene-2,2'-oxiran]-1-yl)ethylidene)-5-oxotetrahydrofuran-3-yl 3-(3,4-dimethoxyphenyl)acrylate
• CAS: 848125-91-7
• 化学式: C₃₁H₄₀O₉
• 分子量: 556.653
• InChiKey: IQQYYPZZIPUDIV-HWEBPZQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  124.05
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  丙酸酐 、 (S,E)-4-(2-((1S,2S,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyloctahydro-1H-spiro[naphthalene-2,2'-oxiran]-1-yl)ethylidene)-5-oxotetrahydrofuran-3-yl 3-(3,4-dimethoxyphenyl)acrylate 反应 0.5h， 生成
  参考文献：
  名称：

  Synthesis and structure–activity relationships of andrographolide analogues as novel cytotoxic agents

  摘要：

  Andrographolide 1, the cytotoxic agent of the plant Androgrophis paniculata was subjected to semi-synthetic studies leading to the preparation of a number of potent and novel analogues. Of the analogues synthesized, while 8,17-epoxy andrographolide 6 retained the cytotoxic activity of 1, ester derivatives of 6 exhibited considerable improvement in activity. Lower activity was observed when the epoxy moiety in the triacetate 9, derived from 6 was modified. Synthesis and structure-activity relationships are discussed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.090
• 作为产物：
  描述：

  3,4-二甲氧基肉桂酸 在 氯甲酸乙酯 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 (S,E)-4-(2-((1S,2S,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyloctahydro-1H-spiro[naphthalene-2,2'-oxiran]-1-yl)ethylidene)-5-oxotetrahydrofuran-3-yl 3-(3,4-dimethoxyphenyl)acrylate
  参考文献：
  名称：

  Synthesis and structure–activity relationships of andrographolide analogues as novel cytotoxic agents

  摘要：

  Andrographolide 1, the cytotoxic agent of the plant Androgrophis paniculata was subjected to semi-synthetic studies leading to the preparation of a number of potent and novel analogues. Of the analogues synthesized, while 8,17-epoxy andrographolide 6 retained the cytotoxic activity of 1, ester derivatives of 6 exhibited considerable improvement in activity. Lower activity was observed when the epoxy moiety in the triacetate 9, derived from 6 was modified. Synthesis and structure-activity relationships are discussed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.090