1-(3-chlorophenyl)-4-phenylpiperazine | 14960-88-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-(3-chlorophenyl)-4-phenylpiperazine
• 英文别名: 1-(3-chloro-phenyl)-4-phenyl-piperazine
• CAS: 14960-88-4
• 化学式: C₁₆H₁₇ClN₂
• 分子量: 272.777
• InChiKey: MEPOEZPIJLMXCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  氯苯 、 1-(3-氯苯基)哌嗪 在 tris-(dibenzylideneacetone)dipalladium(0) 、 di(dicyclohexylamino)phenylphosphine 、 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以67%的产率得到1-(3-chlorophenyl)-4-phenylpiperazine
  参考文献：
  名称：

  Efficient palladium-catalyzed amination of aryl chlorides using di(dicyclohexylamino)phenylphosphine as a PN2 ligand

  摘要：

  The palladium-catalyzed amination of a variety of aryl chlorides has been accomplished by using di(dicyclohexylamino)phenylphosphine (1) as a bulky electron-rich monoaryl phosphine ligand. The optimized condition for the palladium-catalyzed amination of aryl chloride is the followings: aniline (3.0 mmol, 1.0 equiv), chlorobenzene (3.15 mmol, 1.05 equiv), ligand 1 (1 mol %, 0.03 mmol), (KOBu)-Bu-t (4.5 mmol, 1.5 equiv), Pd-2(dba)(3) (1 mol %, 0.03 mmol), and toluene as solvent at reflux temperature. We report on couplings of various amines or chloroamines with chlorobenzenes and heteroaryl chloride. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.059

文献信息

• N -(Pyridin-2-yl)benzamide: efficient ligand for the nickel catalyzed Chan–Lam cross-coupling reaction
  作者：Srinivas Keesara

  DOI：10.1016/j.tetlet.2015.10.047

  日期：2015.12

  An efficient protocol for the Chan–Lam cross-coupling reactions of arylboronic acids with aryl or alkyl amines has been developed by employing simple N-(pyridin-2-yl)benzamide ligand with Ni(OAc)2·4H2O in the presence of TMG base. The reaction proceeded well with high yields by employing various N-nucleophiles at low catalytic loadings.

  通过使用简单的N-（吡啶-2-基）苯甲酰胺配体与Ni（OAc）2 ·4H 2 O的存在，已开发出一种有效的方案，用于芳基硼酸与芳基或烷基胺的Chan–Lam交叉偶联反应TMG基地。通过在低催化负荷下使用各种N-亲核试剂，反应以高收率顺利进行。
• US5084456A
  申请人：——

  公开号：US5084456A

  公开（公告）日：1992-01-28
• Efficient palladium-catalyzed amination of aryl chlorides using di(dicyclohexylamino)phenylphosphine as a PN2 ligand
  作者：Bo Ram Kim、Su-Dong Cho、Eun Jung Kim、In-Hye Lee、Gi Hyeon Sung、Jeum-Jong Kim、Sang-Gyeong Lee、Yong-Jin Yoon

  DOI：10.1016/j.tet.2011.10.059

  日期：2012.1

  The palladium-catalyzed amination of a variety of aryl chlorides has been accomplished by using di(dicyclohexylamino)phenylphosphine (1) as a bulky electron-rich monoaryl phosphine ligand. The optimized condition for the palladium-catalyzed amination of aryl chloride is the followings: aniline (3.0 mmol, 1.0 equiv), chlorobenzene (3.15 mmol, 1.05 equiv), ligand 1 (1 mol %, 0.03 mmol), (KOBu)-Bu-t (4.5 mmol, 1.5 equiv), Pd-2(dba)(3) (1 mol %, 0.03 mmol), and toluene as solvent at reflux temperature. We report on couplings of various amines or chloroamines with chlorobenzenes and heteroaryl chloride. (C) 2011 Elsevier Ltd. All rights reserved.