N-(2-(1-methoxy-5-nitro-1H-indol-3-yl)phenyl)ethanamide | 1512869-13-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N-(2-(1-methoxy-5-nitro-1H-indol-3-yl)phenyl)ethanamide
• 英文别名: N-[2-(1-methoxy-5-nitroindol-3-yl)phenyl]acetamide
• CAS: 1512869-13-4
• 化学式: C₁₇H₁₅N₃O₄
• 分子量: 325.324
• InChiKey: QFGUVMMDCDBZGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  89.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-(1-methoxy-5-nitro-1H-indol-3-yl)phenyl)ethanamide 在 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以91%的产率得到6-methyl-7H-7-methoxy-10-nitro-indolo[2,3-c]quinoline
  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
• 作为产物：
  描述：

  1-硝基-4-亚硝基苯 、 N-(2-ethynylphenyl)acetamide 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以37%的产率得到N-(2-(1-methoxy-5-nitro-1H-indol-3-yl)phenyl)ethanamide
  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.