1-(5-(1-(1H-indol-3-yl)-2-nitroethyl)-2-aminophenyl)ethanone | 1554471-96-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(5-(1-(1H-indol-3-yl)-2-nitroethyl)-2-aminophenyl)ethanone
• 英文别名: 1-[2-amino-5-[1-(1H-indol-3-yl)-2-nitroethyl]phenyl]ethanone
• CAS: 1554471-96-3
• 化学式: C₁₈H₁₇N₃O₃
• 分子量: 323.351
• InChiKey: NWQCXZUQOSKIEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 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：
  105
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(5-(1-(1H-indol-3-yl)-2-nitroethyl)-2-aminophenyl)ethanone 、 苯乙酮 在 indium(III) chloride 作用下， 以 neat (no solvent) 为溶剂， 反应 22.0h， 以86%的产率得到6-(1-(1H-indol-3-yl)-2-nitroethyl)-4-methyl-2-phenylquinoline
  参考文献：
  名称：

  FeCl₃ Catalyzed Regioselective C-Alkylation of Indolylnitroalkenes with Amino Group Substituted Arenes

  摘要：

  An efficient FeCl3 catalyzed protocol for the synthesis of amino functionalized indolylnitroalkanes from easily available precursor indolylnitroalkenes and substituted amines has been developed. Regioselective C-alkylation in the presence of free amino substituted arenes occurred. The scope of this methodology shows good functional group tolerance, and further, this protocol was used to prepare indolylquinoline derivatives.

  DOI：

  10.1021/jo4025368
• 作为产物：
  描述：

  邻氨基苯乙酮 、 3-(2-硝基乙烯基)吲哚 在 iron(III) chloride 作用下， 以 1,2-二溴乙烷 为溶剂， 反应 10.0h， 以83%的产率得到1-(5-(1-(1H-indol-3-yl)-2-nitroethyl)-2-aminophenyl)ethanone
  参考文献：
  名称：

  FeCl₃ Catalyzed Regioselective C-Alkylation of Indolylnitroalkenes with Amino Group Substituted Arenes

  摘要：

  An efficient FeCl3 catalyzed protocol for the synthesis of amino functionalized indolylnitroalkanes from easily available precursor indolylnitroalkenes and substituted amines has been developed. Regioselective C-alkylation in the presence of free amino substituted arenes occurred. The scope of this methodology shows good functional group tolerance, and further, this protocol was used to prepare indolylquinoline derivatives.

  DOI：

  10.1021/jo4025368

文献信息

• FeCl₃ Catalyzed Regioselective <i>C</i>-Alkylation of Indolylnitroalkenes with Amino Group Substituted Arenes
  作者：Manoj R. Zanwar、Veerababurao Kavala、Sachin D. Gawande、Chun-Wei Kuo、Wen-Chang Huang、Ting-Shen Kuo、Hsiu-Ni Huang、Chiu-Hui He、Ching-Fa Yao

  DOI：10.1021/jo4025368

  日期：2014.2.21

  An efficient FeCl3 catalyzed protocol for the synthesis of amino functionalized indolylnitroalkanes from easily available precursor indolylnitroalkenes and substituted amines has been developed. Regioselective C-alkylation in the presence of free amino substituted arenes occurred. The scope of this methodology shows good functional group tolerance, and further, this protocol was used to prepare indolylquinoline derivatives.