2-benzoyl-3-chloro-benzoic acid ethyl ester | 960069-38-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-benzoyl-3-chloro-benzoic acid ethyl ester
• 英文别名: ethyl 2-benzoyl-3-chlorobenzoate；Ethyl 2-benzoyl-3-chlorobenzoate
• CAS: 960069-38-9
• 化学式: C₁₆H₁₃ClO₃
• 分子量: 288.73
• InChiKey: HVTNZISHILGZNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氯苯甲酸乙酯 、 苯甲酰氯 在 TMPMgCl*LiCl 、 copper(I) cyanide di(lithium chloride) 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 以86%的产率得到2-benzoyl-3-chloro-benzoic acid ethyl ester
  参考文献：
  名称：

  Scaleable Preparation of Functionalized Organometallics via Directed Ortho Metalation Using Mg- and Zn-Amide Bases

  摘要：

  A range of aryl and heteroaryl organometallics are efficiently prepared in THF via directed ortho metalation by using the previously reported amide bases tmpMgCl center dot LiCl (tmp = 2,2,6,6-tetramethylpiperidyl), tmp(2)Mg center dot 2LiCl and tmp(2)Zn center dot 2MgCl(2)center dot 2LiCl. These metalation reactions are carried out at 80-100 mmol scale. The unsaturated organometallic compounds undergo smooth reactions with various electrophiles, e.g. additions to carbonyl groups, Pd-catalyzed cross-coupling reactions or Cu-catalyzed acylations. In all cases, the metalation rates have been compared with corresponding small-scale reactions (1-2 mmol). Moreover, a procedure for the recovery of the valuable tmp-H from the aqueous layer is reported.

  DOI：

  10.1021/op9002888

文献信息

• (tmp)2Zn⋅2 MgCl2⋅2 LiCl: A Chemoselective Base for the Directed Zincation of Sensitive Arenes and Heteroarenes
  作者：Stefan H. Wunderlich、Paul Knochel

  DOI：10.1002/anie.200701984

  日期：2007.10.8
• Scaleable Preparation of Functionalized Organometallics <i>via</i> Directed Ortho Metalation Using Mg- and Zn-Amide Bases
  作者：Stefan H. Wunderlich、Christoph J. Rohbogner、Andreas Unsinn、Paul Knochel

  DOI：10.1021/op9002888

  日期：2010.3.19

  A range of aryl and heteroaryl organometallics are efficiently prepared in THF via directed ortho metalation by using the previously reported amide bases tmpMgCl center dot LiCl (tmp = 2,2,6,6-tetramethylpiperidyl), tmp(2)Mg center dot 2LiCl and tmp(2)Zn center dot 2MgCl(2)center dot 2LiCl. These metalation reactions are carried out at 80-100 mmol scale. The unsaturated organometallic compounds undergo smooth reactions with various electrophiles, e.g. additions to carbonyl groups, Pd-catalyzed cross-coupling reactions or Cu-catalyzed acylations. In all cases, the metalation rates have been compared with corresponding small-scale reactions (1-2 mmol). Moreover, a procedure for the recovery of the valuable tmp-H from the aqueous layer is reported.