(S)-2-chloro-3-(1-(N,N-dimethylsulfamoyl)-1H-imidazol-4-yl)propyl-1H-pyrrole-2-carboxylate | 1253796-22-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S)-2-chloro-3-(1-(N,N-dimethylsulfamoyl)-1H-imidazol-4-yl)propyl-1H-pyrrole-2-carboxylate
• 英文别名: [(2S)-2-chloro-3-[1-(dimethylsulfamoyl)imidazol-4-yl]propyl] 1H-pyrrole-2-carboxylate
• CAS: 1253796-22-3
• 化学式: C₁₃H₁₇ClN₄O₄S
• 分子量: 360.821
• InChiKey: WYESGBRRWOURQW-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-chloro-3-(1-(N,N-dimethylsulfamoyl)-1H-imidazol-4-yl)propyl-1H-pyrrole-2-carboxylate 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以52%的产率得到(R)-N,N-dimethyl-4-((1-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazin-4-yl)methyl)-1H-imidazole-1-sulfonamide
  参考文献：
  名称：

  Asymmetric Total Synthesis of ent-Cyclooroidin

  摘要：

  An enantiospecific total synthesis of the pyrrole-imidazole natural product cyclooroidin from histidine is described. The key N1-C9 bond is constructed through an intramolecular SN2-type of reaction of a chloro ester. Subsequent imidazole azidation at the 2-position, pyrrole bromination, azide reduction, and deprotection leads to the completion of the synthesis.

  DOI：

  10.1021/ol1020916
• 作为产物：
  描述：

  吡咯-2-羧酸氯 、 (S)-4-(2-chloro-3-hydroxypropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide 在 4-二甲氨基吡啶 、 D(+)-10-樟脑磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以58%的产率得到(S)-2-chloro-3-(1-(N,N-dimethylsulfamoyl)-1H-imidazol-4-yl)propyl-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Asymmetric Total Synthesis of ent-Cyclooroidin

  摘要：

  An enantiospecific total synthesis of the pyrrole-imidazole natural product cyclooroidin from histidine is described. The key N1-C9 bond is constructed through an intramolecular SN2-type of reaction of a chloro ester. Subsequent imidazole azidation at the 2-position, pyrrole bromination, azide reduction, and deprotection leads to the completion of the synthesis.

  DOI：

  10.1021/ol1020916

文献信息

• Asymmetric Total Synthesis of <i>ent</i>-Cyclooroidin
  作者：Sabuj Mukherjee、Rasapalli Sivappa、Muhammed Yousufuddin、Carl J. Lovely

  DOI：10.1021/ol1020916

  日期：2010.11.5

  An enantiospecific total synthesis of the pyrrole-imidazole natural product cyclooroidin from histidine is described. The key N1-C9 bond is constructed through an intramolecular SN2-type of reaction of a chloro ester. Subsequent imidazole azidation at the 2-position, pyrrole bromination, azide reduction, and deprotection leads to the completion of the synthesis.