2-氯乙基3-甲基苯甲酸酯 | 6639-18-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氯乙基3-甲基苯甲酸酯
• 英文名称: 2-chloroethyl 3-methylbenzoate
• 英文别名: 3-Methyl-benzoesaeure-(2'-chlorethyl)-ester
• CAS: 6639-18-5
• 化学式: C₁₀H₁₁ClO₂
• 分子量: 198.649
• InChiKey: AQYGUKUFDLTLIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,2-二氯乙烷 、 间甲基苯甲酰氯 在 4-二甲氨基吡啶 、 caesium carbonate 作用下， 反应 24.0h， 以91%的产率得到2-氯乙基3-甲基苯甲酸酯
  参考文献：
  名称：

  An Effective Method for the Construction of Esters Using Cs₂CO₃ as Oxygen Source

  摘要：

  An effective method for the construction of esters from acyl chloride and halohydrocarbon using Cs2CO3 as an oxygen source was achieved for the first time. The methodology has a wide scope of substrates and can be scaled up. The study of a preliminary reaction mechanism demonstrated that the 0 in the products comes from Cs2CO3 and this esterification proceeds through a free radical reaction. It was also found that CO2 can also be used in this esterification reaction as an oxygen source.

  DOI：

  10.1021/acs.orglett.5b02479

文献信息

• Palladium(II)-Catalyzed<i>ortho</i>Alkylation of Benzoic Acids with Alkyl Halides
  作者：Yang-Hui Zhang、Bing-Feng Shi、Jin-Quan Yu

  DOI：10.1002/anie.200902262

  日期：2009.8.3

  Outsmarting the competition: In the PdII‐catalyzed reaction of benzoates with alkyl halides, an aryl CH bond is activated before the competitive alkylation of the carboxylate anion can takes place. The alkylation reaction was followed by an intramolecular lactonization to give broadly useful γ‐ and δ‐benzolactones (see scheme).

  战胜竞争：在 Pd II催化的苯甲酸盐与卤代烷的反应中，芳基 C  H 键在羧酸根阴离子的竞争性烷基化发生之前被激活。烷基化反应后进行分子内内酯化，得到广泛有用的 γ- 和 δ-苯内酯（参见方案）。
• An Effective Method for the Construction of Esters Using Cs₂CO₃ as Oxygen Source
  作者：Lanhui Ren、Lianyue Wang、Ying Lv、Guosong Li、Shuang Gao

  DOI：10.1021/acs.orglett.5b02479

  日期：2015.11.6

  An effective method for the construction of esters from acyl chloride and halohydrocarbon using Cs2CO3 as an oxygen source was achieved for the first time. The methodology has a wide scope of substrates and can be scaled up. The study of a preliminary reaction mechanism demonstrated that the 0 in the products comes from Cs2CO3 and this esterification proceeds through a free radical reaction. It was also found that CO2 can also be used in this esterification reaction as an oxygen source.