methyl 4-amino-3-(1H-pyrrol-1-yl)benzoate | 1176666-79-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl 4-amino-3-(1H-pyrrol-1-yl)benzoate
• 英文别名: Methyl 4-amino-3-pyrrol-1-ylbenzoate
• CAS: 1176666-79-7
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: ZFZCGFAQYNYCKT-UHFFFAOYSA-N

物化性质

• 熔点：
  131-133 °C
• 沸点：
  412.5±35.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-戊炔-1-醇 、 methyl 4-amino-3-(1H-pyrrol-1-yl)benzoate 在 platinum(II) bromde 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以98%的产率得到methyl 4,5-dihydro-4-(3-hydroxypropyl)-4-methylpyrrolo[1,2-a]quinoxaline-8-carboxylate
  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：

  吡咯 、 4-氨基-3-碘苯甲酸甲酯 在 potassium phosphate 、 copper(l) iodide 、 N,N'-二甲基乙二胺 作用下， 反应 24.0h， 以44%的产率得到methyl 4-amino-3-(1H-pyrrol-1-yl)benzoate
  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

• Facile Assembly of Fused Isoquinolines by Gold(I)-Catalyzed Coupling-Cyclization Reactions between o-Alkynylbenzaldehydes and Aromatic Amines Containing Tethered Nucleophiles
  作者：Nitin T. Patil、Anil Kumar Mutyala、Pediredla G. V. V. Lakshmi、Penmatcha V. K. Raju、Balasubramanian Sridhar

  DOI：10.1002/ejoc.200901364

  日期：2010.4

  A gold(I)-catalyzed, operationally simple coupling-cyclization technique was developed for the synthesis of isoquinoline-fused polycyclic compounds. The reaction makes use of two coupling partners such as o-alkynylbenzaldehydes and aromatic amines having tethered nucleophiles. The reaction is easy to perform, broad in scope, and allows the generation of a number of biologically important heterocyclic

  开发了一种金 (I) 催化、操作简单的偶联环化技术，用于合成异喹啉稠合多环化合物。该反应利用两个偶联伙伴，例如邻炔基苯甲醛和具有系链亲核试剂的芳香胺。该反应易于进行，范围广泛，并允许从容易获得的起始材料中产生许多生物学上重要的杂环基序。讨论了反应机理。
• Acetic Acid Catalysed One-Pot Synthesis of Pyrrolo[1,2-a]quinoxaline Derivatives
  作者：Pia N. M. Allan、Martyna I. Ostrowska、Bhaven Patel

  DOI：10.1055/s-0039-1690724

  日期：2019.12

  An efficient acetic acid catalysed reaction has been developed for the synthesis of 4-aryl substituted pyrrolo[1,2-a]quinoxalines from readily available starting materials. A range of structures have been synthesised in very good to excellent yields. The one-pot reaction proceeds through imine formation, cyclisation followed by air oxidation.

  已经开发了一种有效的乙酸催化反应，用于从容易获得的起始材料合成 4-芳基取代的吡咯并 [1,2-a] 喹喔啉。已经以非常好到极好的产率合成了一系列结构。一锅反应通过亚胺形成、环化和空气氧化进行。
• 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.