4-fluoro-phenyl cinnamate | 2648-03-5

• 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: 4-fluoro-phenyl cinnamate
• 英文别名: 4-fluorophenyl cinnamate；(4-Fluor-phenyl)-cinnamat
• CAS: 2648-03-5
• 化学式: C₁₅H₁₁FO₂
• 分子量: 242.25
• InChiKey: BZDLWEZWQMSQBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  4-氟苯酚 、 肉桂醛 在 iron(III) chloride 、 potassium carbonate 、 1,3-双-(2,6-二异丙基苯基)咪唑鎓氯化物 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以90%的产率得到4-fluoro-phenyl cinnamate
  参考文献：
  名称：

  NHC /铁协同催化：醛与酚的需氧氧化酯化† ‡

  摘要：

  NHC /铁协同催化系统介导醛与酚的需氧氧化酯化。等摩尔量的反应物的使用导致酯的良好至优异的分离产率。

  DOI：

  10.1039/c1ob05151b

文献信息

• Solvent-free synthesis of 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling of phenols with cinnamic acid catalyzed by molecular iodine
  作者：Durga P. Kamat、Santosh G. Tilve、Vijayendra P. Kamat

  DOI：10.1016/j.tetlet.2012.06.069

  日期：2012.8

  Molecular iodine was used as a catalyst in the [3+3] cyclocoupling of phenols and cinnamic acids which proceeds via a tandem esterification–hydroarylation process at 120–130 °C under solvent-free conditions. Substituted 4-aryl-3,4-dihydrobenzopyran-2-ones were obtained in good yields.

  分子碘被用作苯酚和肉桂酸的[3 + 3]环偶联反应的催化剂，该过程在无溶剂条件下通过串联酯化-氢芳基化过程在120-130°C下进行。以高收率获得了取代的4-芳基-3,4-二氢苯并吡喃-2-酮。
• Molecular iodine catalyst promoted synthesis of chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling
  作者：Mayuri M. Naik、Durga P. Kamat、Santosh G. Tilve、Vijayendra P. Kamat

  DOI：10.1016/j.tet.2014.05.093

  日期：2014.8

  Molecular iodine as an inexpensive catalyst is described in the construction of 2-substituted or 2,2-disubstituted chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling. For the synthesis of chromans, phenols and allylic alcohols were refluxed in chloroform in presence of 20 mol % I-2 while [3+3] cyclocoupling of phenols and cinnamic acids proceeded to give 4-aryl-3,4-dihydrobenzopyran-2-ones using 30 mol % I-2. Later reaction occurs via a tandem hydroarylation-esterification process at 120-130 degrees C under solvent free conditions. Chromans were obtained in 20-92% yields and substituted 4-aryl-3,4-dihydrobenzopyran-2-ones were obtained in 5-85% yields. (C) 2014 Elsevier Ltd. All rights reserved.
• NHC/Iron cooperative catalysis: aerobic oxidative esterification of aldehydes with phenols
  作者：R. Sudarshan Reddy、João N. Rosa、Luís F. Veiros、Stephen Caddick、Pedro M. P. Gois

  DOI：10.1039/c1ob05151b

  日期：——

  An NHC/iron cooperative catalytic system mediates the aerobic oxidative esterification of aldehydes with phenols. The use of equimolar amounts of reactants led to good to excellent isolated yields of esters.

  NHC /铁协同催化系统介导醛与酚的需氧氧化酯化。等摩尔量的反应物的使用导致酯的良好至优异的分离产率。