3-Methyl-but-2-enoic acid 7-methoxy-2-oxo-2H-chromen-4-ylmethyl ester

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-Methyl-but-2-enoic acid 7-methoxy-2-oxo-2H-chromen-4-ylmethyl ester
• 英文别名: (7-Methoxy-2-oxochromen-4-yl)methyl 3-methylbut-2-enoate
• 化学式: C₁₆H₁₆O₅
• 分子量: 288.3
• InChiKey: ZEYDVNZPFXFEPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-甲氧基苯酚 在 硫酸 作用下， 以 乙腈 为溶剂， 反应 2.5h， 生成 3-Methyl-but-2-enoic acid 7-methoxy-2-oxo-2H-chromen-4-ylmethyl ester
  参考文献：
  名称：

  Preliminary Structure–Antiangiogenic Activity Relationships of 4-Senecioyloxymethyl-6,7-dimethoxycoumarin

  摘要：

  Through a systematic modification of the novel angiogenesis inhibitor 4-senecioyloxymethyl-6,7-dimethoxycoumarin (1) we found that a 6,7-dimethoxy moiety is important for bioactivity of 1. Replacement of the lactone functionality in coumarin 1 by an amide decreased its activity. By substitution of the senecioyl chain with various cinnamoyl groups we discovered 6d, bearing a 4-methoxycinnamoyl instead of senecioyl side chain, with inhibitory activity in HUVEC tube formation assay enhanced by one order of magnitude compared to 1. We have also synthesized compound 12, an analogue of 6d, with equipotency and improved water solubility. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00392-x

文献信息

• Photorelease of Incarcerated Caged Acids from Hydrophobic Coumaryl Esters into Aqueous Solution
  作者：Nareshbabu Kamatham、Débora C. Mendes、José P. Da Silva、Richard S. Givens、V. Ramamurthy

  DOI：10.1021/acs.orglett.6b02655

  日期：2016.11.4

  Photolysis of aqueous solutions of carboxylic acid esters of 7-(methoxycoumaryl)-4-methanol included within the capsule made up of two molecules of octaacid released the acids in water. The trigger 7-(methoxycoumaryl)-4-methyl chromophore remains within octaacid either as the alcohol or as an adduct with the host octaacid through a hydrogen abstraction process. The method established here offers a

  由两分子八酸组成的胶囊中包含的7-（甲氧基香豆基芳基）-4-甲醇的羧酸酯水溶液的光解将酸释放到水中。引发剂7-（甲氧基香豆基芳基）-4-甲基发色团以醇形式或通过氢提取过程与主体八酸的加合物形式保留在八酸中。在此建立的方法提供了一种程序，该程序可以及时地在光线下随意释放水中的疏水性酸分子。另外，该系统提供了意外的机会来探究当在疏水性环境中通过香豆基甲基酯光解生成时，同时表现出自由基和离子行为的双自由基类中间体的机械二分法。