Ethyl 2-(3-chloropropyl)-9-oxo-1-azatricyclo[6.3.1.04,12]dodeca-2,4(12),5,7,10-pentaene-10-carboxylate | 1173282-60-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: Ethyl 2-(3-chloropropyl)-9-oxo-1-azatricyclo[6.3.1.04,12]dodeca-2,4(12),5,7,10-pentaene-10-carboxylate
• 英文别名: ethyl 2-(3-chloropropyl)-9-oxo-1-azatricyclo[6.3.1.04,12]dodeca-2,4(12),5,7,10-pentaene-10-carboxylate
• CAS: 1173282-60-4
• 化学式: C₁₇H₁₆ClNO₃
• 分子量: 317.772
• InChiKey: GYQWJYHVHWUWST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  吗啉 、 Ethyl 2-(3-chloropropyl)-9-oxo-1-azatricyclo[6.3.1.04,12]dodeca-2,4(12),5,7,10-pentaene-10-carboxylate 以 二氯甲烷 为溶剂， 反应 24.0h， 以36%的产率得到Ethyl 2-(3-morpholin-4-ylpropyl)-9-oxo-1-azatricyclo[6.3.1.04,12]dodeca-2,4(12),5,7,10-pentaene-10-carboxylate
  参考文献：
  名称：

  Pd/C–Cu in coupling-cyclization process: a general synthesis of 2-substituted 6-oxopyrrolo[3,2,1-ij]quinoline derivatives

  摘要：

  A general and practical synthesis of 2-substituted 6-oxopyrrolo[3,2,1-ij]quinolines has been achieved following a single-step Pd/C-mediated coupling-cyclization strategy. The methodology involves the reaction of 8-iodo-4-oxo-1,4-dihydro quinoline-3-carboxylic acid ethyl ester with a variety of terminal alkynes in the presence of 10% Pd/C-PPh3-CuI as a catalyst system in EtOH. The reaction mechanism and utility of the methodology have been discussed. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.048
• 作为产物：
  描述：

  5-氯戊炔 、 4-羟基-8-碘-3-喹啉羧酸乙酯 在 copper(l) iodide 、 palladium 10% on activated carbon 、 三乙胺 、 三苯基膦 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以45%的产率得到Ethyl 2-(3-chloropropyl)-9-oxo-1-azatricyclo[6.3.1.04,12]dodeca-2,4(12),5,7,10-pentaene-10-carboxylate
  参考文献：
  名称：

  Pd/C–Cu in coupling-cyclization process: a general synthesis of 2-substituted 6-oxopyrrolo[3,2,1-ij]quinoline derivatives

  摘要：

  A general and practical synthesis of 2-substituted 6-oxopyrrolo[3,2,1-ij]quinolines has been achieved following a single-step Pd/C-mediated coupling-cyclization strategy. The methodology involves the reaction of 8-iodo-4-oxo-1,4-dihydro quinoline-3-carboxylic acid ethyl ester with a variety of terminal alkynes in the presence of 10% Pd/C-PPh3-CuI as a catalyst system in EtOH. The reaction mechanism and utility of the methodology have been discussed. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.048

文献信息

• Pd/C–Cu in coupling-cyclization process: a general synthesis of 2-substituted 6-oxopyrrolo[3,2,1-ij]quinoline derivatives
  作者：Mohosin Layek、Vikas Gajare、Dipak Kalita、Aminul Islam、K. Mukkanti、Manojit Pal

  DOI：10.1016/j.tetlet.2009.04.048

  日期：2009.7

  A general and practical synthesis of 2-substituted 6-oxopyrrolo[3,2,1-ij]quinolines has been achieved following a single-step Pd/C-mediated coupling-cyclization strategy. The methodology involves the reaction of 8-iodo-4-oxo-1,4-dihydro quinoline-3-carboxylic acid ethyl ester with a variety of terminal alkynes in the presence of 10% Pd/C-PPh3-CuI as a catalyst system in EtOH. The reaction mechanism and utility of the methodology have been discussed. (c) 2009 Elsevier Ltd. All rights reserved.