ethyl 3-(2-aminophenyl)-2-propynoate | 116659-85-9

• 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: ethyl 3-(2-aminophenyl)-2-propynoate
• 英文别名: (2-amino-phenyl)-propiolic acid ethyl ester；(2-Amino-phenyl)-propiolsaeure-aethylester；(2-Amino-phenyl)-propionsaeure-aethylester；Ethyl 3-(2-aminophenyl)-2-propynoate；ethyl 3-(2-aminophenyl)prop-2-ynoate
• CAS: 116659-85-9
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: MMQDXNQRRYVTJQ-UHFFFAOYSA-N

物化性质

• 熔点：
  54-55 °C
• 沸点：
  326.2±25.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-(2-aminophenyl)-2-propynoate 在 sodium hydroxide 、 乙醚 作用下， 生成 2,4-喹啉二醇
  参考文献：
  名称：

  A Study of the Camps Synthesis of 4-Hydroxy-3-quinolinecarboxylic Acid

  摘要：

  DOI：

  10.1021/ja01639a048
• 作为产物：
  描述：

  靛红 在 三氟化硼乙醚 、 二乙胺 作用下， 以 乙醇 为溶剂， 反应 72.5h， 生成 ethyl 3-(2-aminophenyl)-2-propynoate
  参考文献：
  名称：

  Exploring the Synthetic Versatility of the Lewis Acid Induced Decomposition Reaction of α-Diazo-β-hydroxy Esters. The Case of Ethyl Diazo(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate

  摘要：

  Ethyl diazo(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate was prepared by aldol-type condensation of ethyl diazoacetate with isatin. A systematic and mechanistic study on the Lewis acid induced decomposition reaction of this valuable diazo precursor was carried out with the aim to gain new insights into the mechanistic aspects of the reaction as well as to further understand the factors and experimental conditions which affect the relative product distribution. The reaction, which may proceed via cationic and noncationic mechanisms, was found to be significantly influenced by the reaction environment determined by the characteristics of the Lewis acid employed, by the ability of the Lewis acid to form a complex with the alcohol functionality of the alpha-diazo-beta-hydroxy ester, and by the polarity and nucleophilicity of the solvent used.

  DOI：

  10.1021/jo201205u

文献信息

• TMSOTf-Catalyzed [4 + 2] Annulation of Ynamides and β-(2-Aminophenyl)-α,β-ynones for the Synthesis 2-Aminoquinolines
  作者：Chaofan Qi、Xiaoxiao Shen、Wozheng Fang、Junbiao Chang、Xiao-Na Wang

  DOI：10.1021/acs.orglett.4c00763

  日期：2024.5.3

  A metal-free TMSOTf-catalyzed [4 + 2] annulation of ynamides with β-(2-aminophenyl)-α,β-ynones enables the regiospecific and facile assembly of 2-aminoquinoline frameworks. The catalyst TMSOTf presented a remarkable advancement compared to previously reported transition-metal catalysts. A wide range of 3-aryl/alkyl-substituted 2-aminoquinolines were generated in moderate to excellent yields due to

  无金属 TMSOTf 催化的 ynamides 与 β-(2-氨基苯基)-α,β-ynones 的 [4 + 2] 环化能够实现 2-氨基喹啉框架的区域特异性和轻松组装。与之前报道的过渡金属催化剂相比，催化剂 TMSOTf 呈现出显着的进步。由于条件温和，可以以中等至优异的产率生成多种 3-芳基/烷基取代的 2-氨基喹啉。
• Baeyer; Bloem, Chemische Berichte, 1882, vol. 15, p. 2149
  作者：Baeyer、Bloem

  DOI：——

  日期：——