Ethyl 6-quinolin-7-ylhex-5-ynoate | 1182846-76-9

• 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 6-quinolin-7-ylhex-5-ynoate
• 英文别名: ethyl 6-quinolin-7-ylhex-5-ynoate
• CAS: 1182846-76-9
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: UGBNAHJDCIEFPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  7-氯喹啉 、 5-己炔酸乙酯 在 dicyclohexyl (2’,4’,6-triisopropyl-[1,1’-biphenyl]-2-yl)phosphine 、 palladium diacetate 、 sodium carbonate 作用下， 以 甲苯 为溶剂， 反应 22.0h， 以39%的产率得到Ethyl 6-quinolin-7-ylhex-5-ynoate
  参考文献：
  名称：

  7-Chloroquinoline: a versatile intermediate for the synthesis of 7-substituted quinolines

  摘要：

  A practical synthesis of 7-mono-substituted quinolines has been achieved. Selective reduction of the inexpensive commercial reagent 4,7-dichloroquinoline affords 7-chloroquinoline, which has been converted into more complex 7-mono-substituted quinolines through a series of Pd-catalyzed cross coupling reactions. These studies include the first examples of Suzuki reactions for the preparation of 7-mono-substituted quinolines as well as the first application of the Sonagashira reaction for the synthesis of 7-substituted quinolines. This strategy has been extended to the preparation of 2,7-di-substituted quinolines. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.077

文献信息

• 7-Chloroquinoline: a versatile intermediate for the synthesis of 7-substituted quinolines
  作者：Joshua J. Hirner、Michael J. Zacuto

  DOI：10.1016/j.tetlet.2009.06.077

  日期：2009.9

  A practical synthesis of 7-mono-substituted quinolines has been achieved. Selective reduction of the inexpensive commercial reagent 4,7-dichloroquinoline affords 7-chloroquinoline, which has been converted into more complex 7-mono-substituted quinolines through a series of Pd-catalyzed cross coupling reactions. These studies include the first examples of Suzuki reactions for the preparation of 7-mono-substituted quinolines as well as the first application of the Sonagashira reaction for the synthesis of 7-substituted quinolines. This strategy has been extended to the preparation of 2,7-di-substituted quinolines. (C) 2009 Elsevier Ltd. All rights reserved.