4-chloro-2-(5-chloro-1H-indol-2-yl)benzenamine | 1176666-81-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-chloro-2-(5-chloro-1H-indol-2-yl)benzenamine
• 英文别名: 4-chloro-2-(5-chloro-1H-indol-2-yl)aniline
• CAS: 1176666-81-1
• 化学式: C₁₄H₁₀Cl₂N₂
• 分子量: 277.153
• InChiKey: WLQNTPKLXLXMHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-戊炔-1-醇 、 4-chloro-2-(5-chloro-1H-indol-2-yl)benzenamine 在 platinum(II) bromde 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以89%的产率得到3-(2,8-dichloro-6,11-dihydro-6-methyl-5H-indolo[3,2-c]quinolin-6-yl)propan-1-ol
  参考文献：
  名称：

  Platinum-Catalyzed Formal Markownikoff’s Hydroamination/Hydroarylation Cascade of Terminal Alkynes Assisted by Tethered Hydroxyl Groups

  摘要：

  An efficient method for Markownikoff's hydroamination-hydroarylation of alkynols using PtBr2 as catalyst has been developed. The platinum-catalyzed reactions of alkynols with amino group containing aromatics were achieved in methanol over a reaction time of 6-24 h and temperature ranging from rt to 80 degrees C. This method works well for a variety of alkynols and aromatic amino compounds to give substituted pyrrolo[1,2-a]quinoxalines and indolo[3,2-c]quinolines in good to excellent yields.

  DOI：

  10.1021/jo901200j
• 作为产物：
  描述：

  在 水 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以89%的产率得到4-chloro-2-(5-chloro-1H-indol-2-yl)benzenamine
  参考文献：
  名称：

  Platinum-Catalyzed Formal Markownikoff’s Hydroamination/Hydroarylation Cascade of Terminal Alkynes Assisted by Tethered Hydroxyl Groups

  摘要：

  An efficient method for Markownikoff's hydroamination-hydroarylation of alkynols using PtBr2 as catalyst has been developed. The platinum-catalyzed reactions of alkynols with amino group containing aromatics were achieved in methanol over a reaction time of 6-24 h and temperature ranging from rt to 80 degrees C. This method works well for a variety of alkynols and aromatic amino compounds to give substituted pyrrolo[1,2-a]quinoxalines and indolo[3,2-c]quinolines in good to excellent yields.

  DOI：

  10.1021/jo901200j

文献信息

• Pt(IV)-Catalyzed Hydroamination Triggered Cyclization: A Strategy to Fused Pyrrolo[1,2-<i>a</i>]quinoxalines, Indolo[1,2-<i>a</i>]quinoxalines, and Indolo[3,2-<i>c</i>]quinolines
  作者：Nitin T. Patil、Rahul D. Kavthe、Valmik S. Shinde、Balasubramanian Sridhar

  DOI：10.1021/jo100373w

  日期：2010.5.21

  A PtCl4-catalyzed hydroamination-triggered cyclization strategy to access biologically interesting N-containing heterocycles such as pyrrolo[1,2-a]quinoxalines, indolo[1,2-a]quinoxalines, and indolo[3,2-c]quinolines is described. The reaction makes use of aminoaromatics such as 1-(2-aminophenyl)pyrroles, N-(2-aminophenyl)indoles, 2-(2-aminophenyl)indoles, and alkynes having a tethered hydroxyl group

  一种PtCl 4催化的加氢胺触发的环化策略，以获取生物学上有趣的含N杂环，如吡咯并[1,2- a ]喹喔啉，吲哚[1,2- a ]喹喔啉和吲哚[3,2- c ]喹啉描述。该反应利用氨基芳族化合物，例如1-（2-氨基苯基）吲哚，N-（2-氨基苯基）吲哚，2-（2-氨基苯基）吲哚和具有束缚羟基的炔烃。从机理上讲，该反应非常吸引人，因为它涉及由单一金属催化剂PtCl 4催化的多个催化循环。当反应在微波辅助条件下进行时，我们观察到了速率的显着提高。
• AuI-Catalyzed Direct Hydroamination/Hydroarylation and Double Hydroamination of Terminal Alkynes
  作者：Nitin T. Patil、Pediredla G. V. V. Lakshmi、Vipender Singh

  DOI：10.1002/ejoc.201000389

  日期：2010.8

  An efficient method for formal Markownikoff hydroamination/hydroarylation and double hydroamination of terminal alkynes has been developed. For example, treatment of terminal alkynes with amino-aromatics or diamines in the presence of 2-5 mol-% of Ph 3 PAuNTf 2 in toluene at 100 °C gave the corresponding products in excellent yields. The method was shown to be applicable to a broad range of substrates

  已经开发了一种用于正式 Markownikoff 加氢胺化/加氢芳基化和末端炔烃双加氢胺化的有效方法。例如，在 2-5 mol-% Ph 3 PAuNTf 2 的甲苯溶液存在下，在 100 °C 下，用氨基芳烃或二胺处理末端炔烃，以优异的产率得到相应的产物。该方法被证明适用于广泛的底物，更重要的是，与我们之前报道的方法不同，炔烃中的羟基不是必需的。还讨论了反应机理。
• Platinum-Catalyzed Formal Markownikoff’s Hydroamination/Hydroarylation Cascade of Terminal Alkynes Assisted by Tethered Hydroxyl Groups
  作者：Nitin T. Patil、Rahul D. Kavthe、Vivek S. Raut、Vaddu V. N. Reddy

  DOI：10.1021/jo901200j

  日期：2009.8.21

  An efficient method for Markownikoff's hydroamination-hydroarylation of alkynols using PtBr2 as catalyst has been developed. The platinum-catalyzed reactions of alkynols with amino group containing aromatics were achieved in methanol over a reaction time of 6-24 h and temperature ranging from rt to 80 degrees C. This method works well for a variety of alkynols and aromatic amino compounds to give substituted pyrrolo[1,2-a]quinoxalines and indolo[3,2-c]quinolines in good to excellent yields.