methyl (2-(4-(4-chlorobenzoyl)-1H-pyrrol-3-yl)phenyl)carbamate | 1419177-17-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2-(4-(4-chlorobenzoyl)-1H-pyrrol-3-yl)phenyl)carbamate
• 英文别名: methyl N-[2-[4-(4-chlorobenzoyl)-1H-pyrrol-3-yl]phenyl]carbamate
• CAS: 1419177-17-5
• 化学式: C₁₉H₁₅ClN₂O₃
• 分子量: 354.793
• InChiKey: QYYOXDUQEZKJDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2-(4-(4-chlorobenzoyl)-1H-pyrrol-3-yl)phenyl)carbamate 在 三氯氧磷 作用下， 以 乙腈 为溶剂， 以69%的产率得到4-(4-chlorophenyl)-2H-pyrrolo[3,4-c]quinolone
  参考文献：
  名称：

  TFA-catalyzed C–N bond activation of enamides with indoles: efficient synthesis of 3,3-bisindolylpropanoates and other bisindolylalkanes

  摘要：

  An efficient TFA-catalyzed cleavage of C-N bonds in alkylation of indoles by tertiary enamides was described. A variety of bisindolylalkane derivatives, especially 3,3-bisindolylpropanoates, were expeditiously synthesized in good yields. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.098
• 作为产物：
  描述：

  甲醇 、 4-甲苯磺酰乙腈 、 3-[2-(4-chlorophenyl)-2-oxoethylidene]-1,3-dihydro-2H-indol-2-one 在 potassium tert-butylate 作用下， 反应 4.0h， 以71%的产率得到methyl (2-(4-(4-chlorobenzoyl)-1H-pyrrol-3-yl)phenyl)carbamate
  参考文献：
  名称：

  3-Phenacylideneoxindoles with tosylmethyl isocyanide and MeOH through C–C bond cleavage: facile synthesis of pyrrole and 2H-pyrrolo[3,4-c]quinoline derivatives

  摘要：

  A novel reaction of 3-phenacylideneoxindoles (1) with tosylmethyl isocyanide (2a) and MeOH through C-C bond cleavage has been developed. The reaction proceeded under mild conditions, providing a powerful synthetic tool for the construction of pyrrole derivatives (3) from easily accessible starting materials and synthesis of 2H-pyrrolo[3,4-c]quinolines (4) by further dehydration of 3. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.088

文献信息

• TFA-catalyzed C–N bond activation of enamides with indoles: efficient synthesis of 3,3-bisindolylpropanoates and other bisindolylalkanes
  作者：Hai-Yan Xu、You Zi、Xiao-Ping Xu、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1016/j.tet.2012.11.098

  日期：2013.2

  An efficient TFA-catalyzed cleavage of C-N bonds in alkylation of indoles by tertiary enamides was described. A variety of bisindolylalkane derivatives, especially 3,3-bisindolylpropanoates, were expeditiously synthesized in good yields. (c) 2012 Elsevier Ltd. All rights reserved.
• 3-Phenacylideneoxindoles with tosylmethyl isocyanide and MeOH through C–C bond cleavage: facile synthesis of pyrrole and 2H-pyrrolo[3,4-c]quinoline derivatives
  作者：Rong Wang、Xiao-Ping Xu、Hua Meng、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1016/j.tet.2012.11.088

  日期：2013.2

  A novel reaction of 3-phenacylideneoxindoles (1) with tosylmethyl isocyanide (2a) and MeOH through C-C bond cleavage has been developed. The reaction proceeded under mild conditions, providing a powerful synthetic tool for the construction of pyrrole derivatives (3) from easily accessible starting materials and synthesis of 2H-pyrrolo[3,4-c]quinolines (4) by further dehydration of 3. (C) 2012 Elsevier Ltd. All rights reserved.