2-chlorobenzoic acid 4-chlorophenyl ester | 55372-42-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 2-chlorobenzoic acid 4-chlorophenyl ester
• 英文别名: 2-Chlorobenzoic acid, 4-chlorophenyl ester；(4-chlorophenyl) 2-chlorobenzoate
• CAS: 55372-42-4
• 化学式: C₁₃H₈Cl₂O₂
• 分子量: 267.111
• InChiKey: FAWUTQLFEATJSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  3
• 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
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯乙醇 、 2-chlorobenzoic acid 4-chlorophenyl ester 在 tetrabutylammonium tricarbonylnitrosylferrate 作用下， 以 正己烷 为溶剂， 以84%的产率得到2-chloro-benzoic acid 2-phenylethyl ester
  参考文献：
  名称：

  Nucleophilic Iron Catalysis in Transesterifications: Scope and Limitations

  摘要：

  The ester bond is one of the most common structural motifs found in nature. Apart from the condensation between an acid and an alcohol, transesterifications represent another mechanistic alternative for the preparation of this compound class. The present paper summarizes our most recent investigations in this field, using nucleophilic iron complexes as catalysts for transesterifications under neutral conditions. This new type of metal catalyst complements the existing methodologies, which rely on Lewis acidic metal complexes. Investigations on scope and limitations, stereochemical course, and chemoselectivities will be presented.

  DOI：

  10.1021/jo1004636
• 作为产物：
  描述：

  2-氯苯甲酸 在 Sodium thiosulfate pentahydrate 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 2-chlorobenzoic acid 4-chlorophenyl ester
  参考文献：
  名称：

  通过硫代硫酸钠催化的硫代酸替代物介导的苯酚的位点选择性酰化

  摘要：

  硫代硫酸钠用作硫源，与酸酐反应生成酰基-邦特盐，然后引发与酚类的反应。该协议可用于在存在其他醇基的情况下对酚羟基进行位点选择性酰化。这种酰化方法的优点是操作简单、效率高、使用无味、毒性低的试剂。

  DOI：

  10.1021/acs.orglett.2c01467

文献信息

• Fe-Catalyzed Thioesterification of Carboxylic Esters
  作者：Silja Magens、Bernd Plietker

  DOI：10.1002/chem.201101073

  日期：2011.8.1

  shelf‐stable aryl esters and thiols, a variety of carboxylic acid esters were transformed into the corresponding thioesters with no racemization of labile stereocenters (see scheme). The method was successfully applied in a native chemical‐ligation‐type peptide formation, which suggests that the thiol may act as a co‐catalyst for future 1,2‐additions of pronucleophiles to carboxylic esters.

  第二性质：从稳定的芳基酯和硫醇开始，各种羧酸酯被转化为相应的硫酯，而没有外消旋的立体中心（见方案）。该方法已成功地用于天然化学连接型肽的形成，这表明硫醇可能会作为亲核试剂将来向羧酸酯中添加1,2的助催化剂。
• 一种杂多酸催化酚的芳酯化的合成方法
  申请人：杭州师范大学

  公开号：CN104086344B

  公开（公告）日：2016-02-03

  本发明公开一种杂多酸催化酚的芳酯化的合成方法。在装有温度计、分水器和搅拌器的反应容器中加入脂肪酸取代苯酚酯Ⅰ、取代苯甲酸Ⅱ、反应溶剂和杂多酸，在110～170℃温度下反应0.5～10h，反应过程采用TLC监控反应进程；反应完毕后反应液离心处理，取上清液洗涤脱溶，粗品经重结晶或柱层析得所述的芳香酯类化合物Ⅲ。本方法以杂多酸作为催化剂，和传统的酯化反应相比，后处理简单，也没有用到大量的酸，污染少，对环境友好。所用的杂多酸为固体酸，反应完成后通过过滤可重复套用。采用了酯交换酚的芳酯化反应，避免了反应中取代苯酚容易氧化而带来的副反应，使得操作更简单，产率得到提高。
• Nucleophilic Iron Catalysis in Transesterifications: Scope and Limitations
  作者：Silja Magens、Bernd Plietker

  DOI：10.1021/jo1004636

  日期：2010.6.4

  The ester bond is one of the most common structural motifs found in nature. Apart from the condensation between an acid and an alcohol, transesterifications represent another mechanistic alternative for the preparation of this compound class. The present paper summarizes our most recent investigations in this field, using nucleophilic iron complexes as catalysts for transesterifications under neutral conditions. This new type of metal catalyst complements the existing methodologies, which rely on Lewis acidic metal complexes. Investigations on scope and limitations, stereochemical course, and chemoselectivities will be presented.
• Site-Selective Acylation of Phenols Mediated by a Thioacid Surrogate through Sodium Thiosulfate Catalysis
  作者：Wei-Jr Liao、Sih-Yu Lin、Yu-Shan Kuo、Chien-Fu Liang

  DOI：10.1021/acs.orglett.2c01467

  日期：2022.6.17

  Sodium thiosulfate was used as the sulfur source that reacts with anhydrides to generate acyl-Bunte salts, after which a reaction with phenols was induced. This protocol can be applied for the site-selective acylation of the phenolic hydroxyl group in the presence of other alcoholic groups. The advantages of this acylation method are operational simplicity, high efficiency, and the use of odorless

  硫代硫酸钠用作硫源，与酸酐反应生成酰基-邦特盐，然后引发与酚类的反应。该协议可用于在存在其他醇基的情况下对酚羟基进行位点选择性酰化。这种酰化方法的优点是操作简单、效率高、使用无味、毒性低的试剂。