ethyl 4-(N-n-butyl-N-methylamino)-3-(1-octynyl)benzoate | 874770-28-2

• 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 4-(N-n-butyl-N-methylamino)-3-(1-octynyl)benzoate
• 英文别名: Ethyl 4-[butyl(methyl)amino]-3-oct-1-ynylbenzoate
• CAS: 874770-28-2
• 化学式: C₂₂H₃₃NO₂
• 分子量: 343.51
• InChiKey: LNALNBBIESYMRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4-(N-n-butyl-N-methylamino)-3-(1-octynyl)benzoate 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 ethyl 2-n-hexyl-3-iodo-1-methylindole-5-carboxylate 、 ethyl 1-n-butyl-2-n-hexyl-3-iodoindole-5-carboxylate
  参考文献：
  名称：

  Synthesis of 3-Iodoindoles by the Pd/Cu-Catalyzed Coupling of N,N-Dialkyl-2-iodoanilines and Terminal Acetylenes, Followed by Electrophilic Cyclization

  摘要：

  3-lodoindoles have been prepared in excellent yields by coupling terminal acetylenes with N,N-dialkyl-o-iodoanilines in the presence of a Pd/Cu catalyst, followed by an electrophilic cyclization of the resulting N,N-dialkyl-o-(1-alkynyl)anilines using I-2 in CH2Cl2. Aryl-, vinylic-, alkyl-, and silyl-substituted terminal acetylenes undergo this process to produce excellent yields of 3-iodoindoles. The reactivity of the carbon-nitrogen bond cleavage during cyclization follows the following order: Me > n-Bu, Me > Ph, and cyclohexyl > Me. Subsequent palladium-catalyzed.Sonogashira, Suzuki, and Heck reactions of the resulting 3-iodoindoles proceed smoothly in good yields.

  DOI：

  10.1021/jo051549p
• 作为产物：
  描述：

  4-(丁基氨基)-3-碘苯甲酸乙酯 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 53.0h， 生成 ethyl 4-(N-n-butyl-N-methylamino)-3-(1-octynyl)benzoate
  参考文献：
  名称：

  Synthesis of 3-Iodoindoles by the Pd/Cu-Catalyzed Coupling of N,N-Dialkyl-2-iodoanilines and Terminal Acetylenes, Followed by Electrophilic Cyclization

  摘要：

  3-lodoindoles have been prepared in excellent yields by coupling terminal acetylenes with N,N-dialkyl-o-iodoanilines in the presence of a Pd/Cu catalyst, followed by an electrophilic cyclization of the resulting N,N-dialkyl-o-(1-alkynyl)anilines using I-2 in CH2Cl2. Aryl-, vinylic-, alkyl-, and silyl-substituted terminal acetylenes undergo this process to produce excellent yields of 3-iodoindoles. The reactivity of the carbon-nitrogen bond cleavage during cyclization follows the following order: Me > n-Bu, Me > Ph, and cyclohexyl > Me. Subsequent palladium-catalyzed.Sonogashira, Suzuki, and Heck reactions of the resulting 3-iodoindoles proceed smoothly in good yields.

  DOI：

  10.1021/jo051549p

文献信息

• Synthesis of 3-Iodoindoles by the Pd/Cu-Catalyzed Coupling of <i>N,N</i>-Dialkyl-2-iodoanilines and Terminal Acetylenes, Followed by Electrophilic Cyclization
  作者：Dawei Yue、Tuanli Yao、Richard C. Larock

  DOI：10.1021/jo051549p

  日期：2006.1.1

  3-lodoindoles have been prepared in excellent yields by coupling terminal acetylenes with N,N-dialkyl-o-iodoanilines in the presence of a Pd/Cu catalyst, followed by an electrophilic cyclization of the resulting N,N-dialkyl-o-(1-alkynyl)anilines using I-2 in CH2Cl2. Aryl-, vinylic-, alkyl-, and silyl-substituted terminal acetylenes undergo this process to produce excellent yields of 3-iodoindoles. The reactivity of the carbon-nitrogen bond cleavage during cyclization follows the following order: Me > n-Bu, Me > Ph, and cyclohexyl > Me. Subsequent palladium-catalyzed.Sonogashira, Suzuki, and Heck reactions of the resulting 3-iodoindoles proceed smoothly in good yields.