E-2,4’-dihydroxy-3-methoxystilbene

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: E-2,4’-dihydroxy-3-methoxystilbene
• 英文别名: 2-[(E)-2-(4-hydroxyphenyl)ethenyl]-6-methoxyphenol
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: IUDMJQLUJWAYCS-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  8-methoxy-3-(4’-hydroxyphenyl)coumarin 在 potassium hydroxide 作用下， 以 1,2-丙二醇 为溶剂， 反应 0.5h， 以75%的产率得到E-2,4’-dihydroxy-3-methoxystilbene
  参考文献：
  名称：

  α，β-不饱和芳族内酯的脱羧作用：由3-芳基香豆素或异金龙酮合成E-邻-羟基对苯二酚

  摘要：

  已经建立了一种简单且对环境友好的策略，用于合成E-邻-羟基对苯二酚。两种α，β不饱和芳族内酯，的即3-arylcoumarins和isoaurones，既可以容易地进行在KOH的存在下水解级联/脱羧反应在乙二醇，得到期望的E-邻-hydroxystilbenes在中度至高产。

  DOI：

  10.1039/c7gc02994b

文献信息

• Synthesis and antiproliferative evaluation of 2-hydroxylated (E)-stilbenes
  作者：Yan Zhang、Mingyun Shen、Sunliang Cui、Tingjun Hou

  DOI：10.1016/j.bmcl.2014.10.009

  日期：2014.12

  A simple synthesis of 2-hydroxylated (E)-stilbenes was accomplished in good yields via oxidative coupling of 2-hydroxystyrenes and arylboronic acids, with Rh(III)-catalyst and Cu(OAc)(2) as oxidant. The antiproliferative evaluation of all the synthesized compounds were assessed on four different human cancer cell lines (Colo-205, MDA-468, HT29, and MGC80-3), and the results showed that several compounds exhibit strong antiproliferative activities (up to IC50 = 35 nM for MGC80-3). (C) 2014 Elsevier Ltd. All rights reserved.
• Decarboxylation of α,β-unsaturated aromatic lactones: synthesis of<i>E-ortho</i>-hydroxystilbenes from 3-arylcoumarins or isoaurones
  作者：Xihua Huang、Jie Liu、Jianfei Sheng、Xianheng Song、Zhibo Du、Mingkang Li、Xuejing Zhang、Yong Zou

  DOI：10.1039/c7gc02994b

  日期：——

  A simple and environmentally friendly strategy for the synthesis of E-ortho-hydroxystilbenes has been established. Two kinds of α,β-unsaturated aromatic lactones, i.e. the 3-arylcoumarins and the isoaurones, could both readily undergo a cascade hydrolyzation/decarboxylation reaction in the presence of KOH in ethylene glycol to afford the desired E-ortho-hydroxystilbenes in moderate to high yields.

  已经建立了一种简单且对环境友好的策略，用于合成E-邻-羟基对苯二酚。两种α，β不饱和芳族内酯，的即3-arylcoumarins和isoaurones，既可以容易地进行在KOH的存在下水解级联/脱羧反应在乙二醇，得到期望的E-邻-hydroxystilbenes在中度至高产。