1-methoxy-5-nitro-3-(4-nitrophenyl)-1H-indole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-methoxy-5-nitro-3-(4-nitrophenyl)-1H-indole
• 化学式: C₁₅H₁₁N₃O₅
• 分子量: 313.269
• InChiKey: OLLUKTKDEPWIKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  100.44
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  1-乙炔基-4-硝基苯 、 1-硝基-4-亚硝基苯 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以91%的产率得到1-methoxy-5-nitro-3-(4-nitrophenyl)-1H-indole
  参考文献：
  名称：

  A simple, efficient, regioselective and one-pot preparation of N-hydroxy- and N–O-protected hydroxyindoles via cycloaddition of nitrosoarenes with alkynes. Synthetic scope, applications and novel by-products

  摘要：

  The thermal reaction between nitrosoarenes and alkynes under alkylating conditions produces N-alkoxyindoles as the major products in moderate to good yields and excellent regioselectivity. Various electrophiles are used affording different N-O-protected hydroxyindoles in a multi-component fashion. Privileged acetylenic substrates used in reactions with substituted nitrosoarenes are arylalkynes or propiolates. Potentially bioactive compounds and other classes of highly functionalizable indole products were prepared. Reactions between D-carbomethoxy-nitrosoarenes and arylacetylenes provided tricyclic compounds containing an acylaziridine indoline skeleton. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.072

文献信息

• A simple, efficient, regioselective and one-pot preparation of N-hydroxy- and N–O-protected hydroxyindoles via cycloaddition of nitrosoarenes with alkynes. Synthetic scope, applications and novel by-products
  作者：Gabriella Ieronimo、Alessandro Mondelli、Francesco Tibiletti、Angelo Maspero、Giovanni Palmisano、Simona Galli、Stefano Tollari、Norberto Masciocchi、Kenneth M. Nicholas、Silvia Tagliapietra、Giancarlo Cravotto、Andrea Penoni

  DOI：10.1016/j.tet.2013.10.072

  日期：2013.12

  The thermal reaction between nitrosoarenes and alkynes under alkylating conditions produces N-alkoxyindoles as the major products in moderate to good yields and excellent regioselectivity. Various electrophiles are used affording different N-O-protected hydroxyindoles in a multi-component fashion. Privileged acetylenic substrates used in reactions with substituted nitrosoarenes are arylalkynes or propiolates. Potentially bioactive compounds and other classes of highly functionalizable indole products were prepared. Reactions between D-carbomethoxy-nitrosoarenes and arylacetylenes provided tricyclic compounds containing an acylaziridine indoline skeleton. (C) 2013 Elsevier Ltd. All rights reserved.