2-(4-Chlorophenyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid

• 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: 2-(4-Chlorophenyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid
• 化学式: C₁₆H₁₃ClO₄
• 分子量: 304.73
• InChiKey: TYMGHKPVWLZIHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-Chlorophenyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid 在 N-甲基咪唑 、 碳酸氢钠 作用下， 反应 0.33h， 以78%的产率得到(E)-4'-chloro-4-hydroxy-3-methoxystilbene
  参考文献：
  名称：

  Remarkable synergism in methylimidazole-promoted decarboxylation of substituted cinnamic acid derivatives in basic water medium under microwave irradiation: a clean synthesis of hydroxylated (E)-stilbenes

  摘要：

  A metal-free protocol for decarboxylation of substituted alpha-phenylcinnamic acid derivatives in aqueous media is developed, wherein a remarkable synergism between methylimidazole and aq NaHCO3 in polyethylene glycol under microwave furnished the corresponding para/ortho hydroxylated (E)-stilbenes in a mild and efficient manner. The critical role of water in facilitating the decarboxylation imparts an interesting facet to the synthetic utility of water mediated organic transformations. The developed protocol provides a clean alternative to the hitherto indispensable multistep approaches involving toxic quinoline and a copper salt combination as the common decarboxylating agent. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.046

文献信息

• Divergent Reactivity in Cu^II-Catalyzed Oxidative Coupling between Indole/Tryptamine Derivatives and β-Arylacrylic Acids
  作者：Wei Cao、Jinbao Fan、Linyang Yan、Guangyao Zeng、Jinjin Ma、Yajing Wang、Yingjun Zhou、Xu Deng

  DOI：10.1021/acs.orglett.9b03697

  日期：2019.12.6

  Condition-controlled divergent oxidative coupling reactions between indole/tryptamine derivatives and β-arylacrylic acids with the catalysis of copper(II) have been developed. Specifically, a formal Michael addition/dehydration sequence between indoles and β-arylacrylic acids occurred in the presence of catalytic CuBr2 in CH3CN under air, thus affording highly functionalized 2,3-dihydro-1H-pyrrolo[1

  已经开发出条件控制的吲哚/色胺衍生物与β-芳基丙烯酸之间的氧化偶联反应，其催化铜（II）。具体而言，在空气中CH 3 CN中存在催化CuBr 2时，吲哚与β-芳基丙烯酸之间存在正式的迈克尔加成/脱水序列，从而提供了高度官能化的2,3-二氢-1 H-吡咯并[1,2- a ]吲哚。相反，在将氧化剂改变为t BuOOH，将溶剂改变为DCM时，反应过程切换到空前的氧化偶合/环化级联反应，从而选择性地得到四环吡咯并[2,3- b ]二氢吲哚。
• Remarkable synergism in methylimidazole-promoted decarboxylation of substituted cinnamic acid derivatives in basic water medium under microwave irradiation: a clean synthesis of hydroxylated (E)-stilbenes
  作者：Vinod Kumar、Abhishek Sharma、Anuj Sharma、Arun K. Sinha

  DOI：10.1016/j.tet.2007.05.046

  日期：2007.8

  A metal-free protocol for decarboxylation of substituted alpha-phenylcinnamic acid derivatives in aqueous media is developed, wherein a remarkable synergism between methylimidazole and aq NaHCO3 in polyethylene glycol under microwave furnished the corresponding para/ortho hydroxylated (E)-stilbenes in a mild and efficient manner. The critical role of water in facilitating the decarboxylation imparts an interesting facet to the synthetic utility of water mediated organic transformations. The developed protocol provides a clean alternative to the hitherto indispensable multistep approaches involving toxic quinoline and a copper salt combination as the common decarboxylating agent. (C) 2007 Elsevier Ltd. All rights reserved.