ethyl 3-iodo-1-methyl-2-phenylindole-5-carboxylate | 681259-71-2

• 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 3-iodo-1-methyl-2-phenylindole-5-carboxylate
• 英文别名: 1H-Indole-5-carboxylic acid, 3-iodo-1-methyl-2-phenyl-, ethyl ester
• CAS: 681259-71-2
• 化学式: C₁₈H₁₆INO₂
• 分子量: 405.235
• InChiKey: SFVHSLFBMBBLFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ethyl 4-(N,N-dimethylamino)-3-(2-phenylethynyl)benzoate 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 ethyl 3-iodo-1-methyl-2-phenylindole-5-carboxylate
  参考文献：
  名称：

  Friedel-Crafts Arylation形成C ？C键：从芳基三氮烯到不对称和功能化的多环芳烃的途径

  摘要：

  环，环，环：实现了由芳基三氮烯合成多环芳烃的Friedel-Crafts分子内芳基化反应。可以使用此方法制备由五元，六元和七元环组成的多环芳族化合物。

  DOI：

  10.1002/anie.201206578

文献信息

• Synthesis of 3-Iodoindoles by Electrophilic Cyclization of <i>N</i>,<i>N</i>-Dialkyl-2-(1-alkynyl)anilines
  作者：Dawei Yue、Richard C. Larock

  DOI：10.1021/ol0498996

  日期：2004.3.1

  A wide variety of N-alkyl-3-iodoindoles are readily prepared under very mild reaction conditions by the palladium/copper-catalyzed cross-coupling of N,N-dialkyl-o-iodoanilines and terminal alkynes, followed by electrophilic cyclization by I-2. Alkyl-, aryl-, and vinylic-substituted alkynes all undergo iodocyclization in excellent yields.
• 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.
• Friedel-Crafts Arylation for the Formation of C sp 2C sp 2 Bonds: A Route to Unsymmetrical and Functionalized Polycyclic Aromatic Hydrocarbons from Aryl Triazenes
  作者：Jun Zhou、Weijun Yang、Binjie Wang、Hongjun Ren

  DOI：10.1002/anie.201206578

  日期：2012.12.3

  Rings, rings, rings: A Friedel–Crafts intramolecular arylation for the synthesis of polycyclic aromatic hydrocarbons from aryl triazenes has been achieved. Polycyclic aromatic compounds consisting of five‐, six‐, and seven‐membered rings can be prepared using this method.

  环，环，环：实现了由芳基三氮烯合成多环芳烃的Friedel-Crafts分子内芳基化反应。可以使用此方法制备由五元，六元和七元环组成的多环芳族化合物。