2-cyclohex-1-enyl-5-nitro-1H-indol-7-ylamine | 1180556-91-5

• 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: 2-cyclohex-1-enyl-5-nitro-1H-indol-7-ylamine
• 英文别名: 2-(cyclohexen-1-yl)-5-nitro-1H-indol-7-amine
• CAS: 1180556-91-5
• 化学式: C₁₄H₁₅N₃O₂
• 分子量: 257.292
• InChiKey: KLXLCLRCLCPZKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  87.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-cyclohex-1-enyl-5-nitro-1H-indol-7-ylamine 、 碘甲烷 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以66%的产率得到(2-cyclohex-1-enyl-1-methyl-5-nitro-1H-indol-7-yl)-dimethylamine
  参考文献：
  名称：

  Straightforward selective preparation of nitro- or amino-indoles from 2-halonitroanilines and alkynes. First synthesis of 7-amino-5-nitroindoles

  摘要：

  A one-pot selective synthesis of 2-substituted C5-, C6-, and C7-nitro- or amino-indoles has been developed from 2-halonitroanilines. These two types of nitrogen-substituted indoles have been selectively obtained by only varying the solvent used in the tandem Sonogashira coupling/heteroannulation reaction. Moreover, from commercially available 2-bromo-4,6-dinitroaniline an unprecedented in situ selective reduction of one of the nitro groups has allowed the synthesis of new 7-amino-5-nitro-2-substituted indoles. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.05.027
• 作为产物：
  描述：

  1-乙炔基环己烷 、 2-溴-4,6-二硝基苯胺 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二乙胺 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以36%的产率得到2-cyclohex-1-enyl-5-nitro-1H-indol-7-ylamine
  参考文献：
  名称：

  Straightforward selective preparation of nitro- or amino-indoles from 2-halonitroanilines and alkynes. First synthesis of 7-amino-5-nitroindoles

  摘要：

  A one-pot selective synthesis of 2-substituted C5-, C6-, and C7-nitro- or amino-indoles has been developed from 2-halonitroanilines. These two types of nitrogen-substituted indoles have been selectively obtained by only varying the solvent used in the tandem Sonogashira coupling/heteroannulation reaction. Moreover, from commercially available 2-bromo-4,6-dinitroaniline an unprecedented in situ selective reduction of one of the nitro groups has allowed the synthesis of new 7-amino-5-nitro-2-substituted indoles. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.05.027

文献信息

• Straightforward selective preparation of nitro- or amino-indoles from 2-halonitroanilines and alkynes. First synthesis of 7-amino-5-nitroindoles
  作者：Roberto Sanz、Verónica Guilarte、Antonio Pérez

  DOI：10.1016/j.tetlet.2009.05.027

  日期：2009.8

  A one-pot selective synthesis of 2-substituted C5-, C6-, and C7-nitro- or amino-indoles has been developed from 2-halonitroanilines. These two types of nitrogen-substituted indoles have been selectively obtained by only varying the solvent used in the tandem Sonogashira coupling/heteroannulation reaction. Moreover, from commercially available 2-bromo-4,6-dinitroaniline an unprecedented in situ selective reduction of one of the nitro groups has allowed the synthesis of new 7-amino-5-nitro-2-substituted indoles. (C) 2009 Elsevier Ltd. All rights reserved.