5-[4-((1S,5S,6R)-6-Benzyloxycarbonyl-1-ethoxycarbonyl-5-methyl-4-oxo-2,3-diphenyl-bicyclo[3.1.0]hex-2-en-6-yl)-1-methyl-1H-imidazol-2-yl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 4-benzyl ester 2-ethyl ester | 131213-35-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-[4-((1S,5S,6R)-6-Benzyloxycarbonyl-1-ethoxycarbonyl-5-methyl-4-oxo-2,3-diphenyl-bicyclo[3.1.0]hex-2-en-6-yl)-1-methyl-1H-imidazol-2-yl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 4-benzyl ester 2-ethyl ester
• 英文别名: 4-O-benzyl 2-O-ethyl 5-[4-[(1S,5S,6R)-1-ethoxycarbonyl-5-methyl-4-oxo-2,3-diphenyl-6-phenylmethoxycarbonyl-6-bicyclo[3.1.0]hex-2-enyl]-1-methylimidazol-2-yl]-3-methyl-1H-pyrrole-2,4-dicarboxylate
• CAS: 131213-35-9
• 化学式: C₅₀H₄₅N₃O₉
• 分子量: 831.922
• InChiKey: IFJXJHXFNKNQMN-JYAKJWHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  62
• 可旋转键数：
  18
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  156
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5-[4-((1S,5S,6R)-6-Benzyloxycarbonyl-1-ethoxycarbonyl-5-methyl-4-oxo-2,3-diphenyl-bicyclo[3.1.0]hex-2-en-6-yl)-1-methyl-1H-imidazol-2-yl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 4-benzyl ester 2-ethyl ester 在 manganese(IV) oxide 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.75h， 生成 4-Formyl-5-[4-((3aR,3bR,4R,6aR)-4-hydroxy-3b-methyl-3-oxo-5,6-diphenyl-3b,4-dihydro-2-oxa-cyclopropadicyclopenten-3a-yl)-1-methyl-1H-imidazol-2-yl]-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Reaction of pyrrolo[1,2-c]imidazole mesomeric betaines with diphenylcyclopropenone derivatives

  摘要：

  The cyloaddition reactions of title mesomeric betaines to diphenylcyclopropenone and diphenylcyclopropenethione have been studied. Cycloadditions lead to either 2(1H)-pyridone, 2(1H)-pyridinethione, or bicyclo[3.1.0]hex-3-en-2-one derivatives. Formation of the bicyclo[3.1.0]hex-3-en-2-ones is highly stereoselective with exclusive formation of C-6 exo-alkoxycarbonyl or the exo-acetyl diastereoisomer. Diphenylcyclopropenone and its thione enriched with C-13 at both the 2- and 3-positions were prepared and used to determine the structures of the cycloaddition products. Possible mechanistic pathways for these reactions are considered and compared with previous postulated mechanisms for the cycloadditions of cyclopropenones to N-heterocycles and enamines.

  DOI：

  10.1021/jo00001a023
• 作为产物：
  描述：

  7-((benzyloxy)carbonyl)-3-(3-((benzyloxy)carbonyl)-5-(ethoxycarbonyl)-4-methyl-1H-pyrrol-2-yl)-5-(ethoxycarbonyl)-2,6-dimethyl-1H-pyrrolo[1,2-c]imidazol-2-ium-1-ide 、 二苯基环丙烯酮 以 苯 为溶剂， 反应 3.5h， 以83%的产率得到5-[4-((1S,5S,6R)-6-Benzyloxycarbonyl-1-ethoxycarbonyl-5-methyl-4-oxo-2,3-diphenyl-bicyclo[3.1.0]hex-2-en-6-yl)-1-methyl-1H-imidazol-2-yl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 4-benzyl ester 2-ethyl ester
  参考文献：
  名称：

  Reaction of pyrrolo[1,2-c]imidazole mesomeric betaines with diphenylcyclopropenone derivatives

  摘要：

  The cyloaddition reactions of title mesomeric betaines to diphenylcyclopropenone and diphenylcyclopropenethione have been studied. Cycloadditions lead to either 2(1H)-pyridone, 2(1H)-pyridinethione, or bicyclo[3.1.0]hex-3-en-2-one derivatives. Formation of the bicyclo[3.1.0]hex-3-en-2-ones is highly stereoselective with exclusive formation of C-6 exo-alkoxycarbonyl or the exo-acetyl diastereoisomer. Diphenylcyclopropenone and its thione enriched with C-13 at both the 2- and 3-positions were prepared and used to determine the structures of the cycloaddition products. Possible mechanistic pathways for these reactions are considered and compared with previous postulated mechanisms for the cycloadditions of cyclopropenones to N-heterocycles and enamines.

  DOI：

  10.1021/jo00001a023