ethyl 2-amino-5-methyl-1H-indole-3-carboxylate | 365547-96-2

• 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: ethyl 2-amino-5-methyl-1H-indole-3-carboxylate
• CAS: 365547-96-2
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: JSPKRYYAXVBOQB-UHFFFAOYSA-N

物化性质

• 熔点：
  208-209 °C
• 沸点：
  412.3±40.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  68.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-amino-5-methyl-1H-indole-3-carboxylate 、 1-(4-methoxyphenyl)-3-(p-tolyl)prop-2-yn-1-one 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 ethyl 2-(4-methoxyphenyl)-8-methyl-4-(4-methylphenyl)pyrimido-[1,2-a]indole-10-carboxylate
  参考文献：
  名称：

  Three-component tandem reaction involving acid chlorides, terminal alkynes, and ethyl 2-amino-1H-indole-3-carboxylates: synthesis of highly diversified pyrimido[1,2-a]indoles via sequential Sonogashira and [3+3] cyclocondensation reactions

  摘要：

  A simple, highly efficient three-component reaction involving acid chlorides, terminal alkynes, and ethyl 2-amino-1H-indole-3-carboxylates, for the synthesis of highly diversified pyrimido[1,2-a]indoles has been described. The salient feature of the reaction involves sequential Sonogashira and [3+3] cyclocondensation reactions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.06.021
• 作为产物：
  描述：

  N-(2-bromo-4-methylphenyl)-2,2,2-trifluoroacetamide 、 氰乙酸乙酯 在 potassium carbonate 、 L-脯氨酸 、 copper(l) iodide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 12.25h， 以73%的产率得到ethyl 2-amino-5-methyl-1H-indole-3-carboxylate
  参考文献：
  名称：

  A Simple Copper-Catalyzed Cascade Synthesis of 2-Amino-1H-indole-3-carboxylate Derivatives

  摘要：

  AbstractWe have developed a simple and efficient copper‐catalyzed method for the synthesis of 2‐amino‐1H‐indole‐3‐carboxylate derivatives via cascade reactions of substituted N‐(2‐halophenyl)‐2,2,2‐trifluoroacetamide with alkyl 2‐cyanoacetate or malononitrile under mild conditions, and the method is of wide practical application.

  DOI：

  10.1002/adsc.200900887

文献信息

• Diversity-Oriented Synthesis of Polycyclic Indoles: Brønsted or Lewis Acid Catalyzed Three-Component Reaction for the Synthesis of α-Carbolines and Pyrimidoindoles
  作者：Rajesh K. Arigela、Ravi Kumar、Srinivas Samala、Sahaj Gupta、Bijoy Kundu

  DOI：10.1002/ejoc.201402633

  日期：2014.9

  diversity-oriented synthesis of pyrido- and pyrimido-indoles from an acid-catalyzed three component (3C) reaction involving ethyl 2-amino-1H-indole-3-carboxylates, arylaldehydes, and terminal alkynes. In the presence of a Bronsted acid such as trifluoroacetic acid (TFA), the 3C reaction furnished a mixture of pyrido- and pyrimido-indoles, whereas when catalyzed by Yb(OTf)3 as a Lewis acid, pyrimidoindoles

  我们报告了从涉及 2-氨基-1H-吲哚-3-羧酸乙酯、芳醛和末端炔烃的酸催化三组分 (3C) 反应中合成吡啶和嘧啶并吲哚的多样性。在布朗斯台德酸如三氟乙酸 (TFA) 的存在下，3C 反应提供了吡啶和嘧啶并吲哚的混合物，而当由 Yb(OTf)3 作为路易斯酸催化时，得到嘧啶吲哚作为单一产物. 这些发现证明了通过改变酸催化剂来控制反应产物的能力。TFA 催化的 3C 反应的显着特征是炔丙胺形成后在一个锅中遵循两种不同的途径。
• Lewis-Acid-Catalyzed Decarboxylative Annulation of 2-Aminoindole-3-Carboxylate with Ynals Involving [3 + 2] Spirocycloaddition and 2,3-Aza Migration
  作者：Manda Rajesh、Ravi Kumar、Surendra Puri、Jagadeesh Babu Nanubolu、Maddi Sridhar Reddy

  DOI：10.1021/acs.orglett.9b04626

  日期：2020.2.7

  2-Aminoindole-3-carboxylates undergo a Lewis-acid-catalyzed decarboxylative annulation with ynals to afford dihydro-chromeno-fused delta-carbolines through a 2,3-aza migration, via a spirocyclic intermediate generated from an initial [3 + 2] spirocycloaddition. Bronsted acid interference changes the path from a [3 + 2] to a [4 + 2] addition. 2-Aminoindoles without an ester functional group at C3 underwent a different condensation, followed by hetero-Diels Alder reaction to generate chromeno-fused alpha-carbolines.