(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 | 1253796-23-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (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
• 英文别名: N,N-dimethyl-4-[[(4R)-1-oxo-3,4-dihydropyrrolo[2,1-c][1,4]oxazin-4-yl]methyl]imidazole-1-sulfonamide
• CAS: 1253796-23-4
• 化学式: C₁₃H₁₆N₄O₄S
• 分子量: 324.36
• InChiKey: FNNQBEXIZGHDSF-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  94.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (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 、 sodium methylate 以 甲醇 为溶剂， 反应 8.0h， 以35%的产率得到(R)-methyl 1-(1-(1-(N,N-dimethylsulfamoyl)-1H-imidazol-4-yl)-3-hydroxypropan-2-yl)-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
• 作为产物：
  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