ethyl 2-[(ethoxycarbonyl)amino]-1H-indole-1-carboxylate | 1262587-65-4

• 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-[(ethoxycarbonyl)amino]-1H-indole-1-carboxylate
• 英文别名: Ethyl 2-(ethoxycarbonylamino)indole-1-carboxylate
• CAS: 1262587-65-4
• 化学式: C₁₄H₁₆N₂O₄
• 分子量: 276.292
• InChiKey: DPYGYVNOJWECMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(ethoxycarbonyl)amino]-1H-indole-1-carboxylate 、 1-(4-chlorophenyl)-3-phenylprop-2-yn-1-ol 在 碘 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以93%的产率得到ethyl 2-[(ethoxycarbonyl)amino]-3-[1-(4-chlorophenyl)-3-phenylprop-2-ynyl]-1H-indole-1-carboxylate
  参考文献：
  名称：

  Three component tandem reactions involving protected 2-amino indoles, disubstituted propargyl alcohols, and I2/ICl: iodo-reactant controlled synthesis of dihydro-α-carbolines and α-carbolines via iodo-cyclization/iodo-cycloelimination

  摘要：

  Two simple, highly efficient three component tandem reactions for the synthesis of diversified N-a N-b dicarbamate-4,9-dihydro-3-iodo-alpha-carbolines and N-a-carbamate-3-iodo-alpha-carbolines have been described. The strategy involves one-pot condensation of bis-carbamate protected 2-amino indoles with disubstituted propargyl alcohols and I-2/ICl. The salient feature of the reaction involves iodocyclo-elimination of N-b-linked carbamate under mild condition in the final step. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.147
• 作为产物：
  描述：

  氯甲酸乙酯 、 1H-吲哚-2-胺盐酸盐 在 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以78%的产率得到ethyl 2-[(ethoxycarbonyl)amino]-1H-indole-1-carboxylate
  参考文献：
  名称：

  Three component tandem reactions involving protected 2-amino indoles, disubstituted propargyl alcohols, and I2/ICl: iodo-reactant controlled synthesis of dihydro-α-carbolines and α-carbolines via iodo-cyclization/iodo-cycloelimination

  摘要：

  Two simple, highly efficient three component tandem reactions for the synthesis of diversified N-a N-b dicarbamate-4,9-dihydro-3-iodo-alpha-carbolines and N-a-carbamate-3-iodo-alpha-carbolines have been described. The strategy involves one-pot condensation of bis-carbamate protected 2-amino indoles with disubstituted propargyl alcohols and I-2/ICl. The salient feature of the reaction involves iodocyclo-elimination of N-b-linked carbamate under mild condition in the final step. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.147

文献信息

• Three component tandem reactions involving protected 2-amino indoles, disubstituted propargyl alcohols, and I2/ICl: iodo-reactant controlled synthesis of dihydro-α-carbolines and α-carbolines via iodo-cyclization/iodo-cycloelimination
  作者：Sudhir K. Sharma、Sahaj Gupta、Mohammad Saifuddin、Anil K. Mandadapu、Piyush K. Agarwal、Harsh M. Gauniyal、Bijoy Kundu

  DOI：10.1016/j.tetlet.2010.10.147

  日期：2011.1

  Two simple, highly efficient three component tandem reactions for the synthesis of diversified N-a N-b dicarbamate-4,9-dihydro-3-iodo-alpha-carbolines and N-a-carbamate-3-iodo-alpha-carbolines have been described. The strategy involves one-pot condensation of bis-carbamate protected 2-amino indoles with disubstituted propargyl alcohols and I-2/ICl. The salient feature of the reaction involves iodocyclo-elimination of N-b-linked carbamate under mild condition in the final step. (C) 2010 Elsevier Ltd. All rights reserved.