methyl (1aS,8R,8aS,8bS)-1,1a,2,8,8a,8b-hexahydro-8-[(acetyloxy)methyl]-7-(benzyloxy)-1-(tert-butyloxycarbonyl)-8-formylazirino[2',3':3,4]pyrrolo[1,2-a]indole-5-carboxylate 3-oxide | 187682-44-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl (1aS,8R,8aS,8bS)-1,1a,2,8,8a,8b-hexahydro-8-[(acetyloxy)methyl]-7-(benzyloxy)-1-(tert-butyloxycarbonyl)-8-formylazirino[2',3':3,4]pyrrolo[1,2-a]indole-5-carboxylate 3-oxide
• 英文别名: 5-O-tert-butyl 12-O-methyl (4S,6S,7S,8R)-8-(acetyloxymethyl)-8-formyl-2-oxido-10-phenylmethoxy-5-aza-2-azoniatetracyclo[7.4.0.02,7.04,6]trideca-1(9),10,12-triene-5,12-dicarboxylate
• CAS: 187682-44-6
• 化学式: C₂₉H₃₂N₂O₉
• 分子量: 552.581
• InChiKey: JWGJKTBBVPNEAG-VOAJYBCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (1aS,8R,8aS,8bS)-1,1a,2,8,8a,8b-hexahydro-8-[(acetyloxy)methyl]-7-(benzyloxy)-1-(tert-butyloxycarbonyl)-8-formylazirino[2',3':3,4]pyrrolo[1,2-a]indole-5-carboxylate 3-oxide 在 乙酸酐 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 41.5h， 生成 methyl (1aS,8R,9S,9aS)-1,1a,2,8,9,9a-hexahydro-8-[(acetyloxy)methyl]-7-(benzyloxy)-1-(tert-butyloxycarbonyl)-8-formyl-9-hydroxy-3,9-epoxy-3H-azirino[2,3-c][1]benzazocin-5-carboxylate
  参考文献：
  名称：

  Chiral Aziridinyl Radicals:  An Application to the Synthesis of the Core Nucleus of FR-900482

  摘要：

  An asymmetric route to the core nucleus of the antitumor agent FR-900482 utilizes the cyclization of an aziridinyl radical into a functionalized indole nucleus. The route employs a selective Polonovski reaction and the Hootele-Dmitrienko rearrangement to install two oxygen atoms.

  DOI：

  10.1021/jo961992n
• 作为产物：
  描述：

  methyl (1aS,8R,8aS,8bR)-1,1a,2,8,8a,8b-hexahydro-7-(benzyloxy)-1-(tert-butyloxycarbonyl)-8-formyl-8-(hydroxymethyl)azirino[2',3':3,4]pyrrolo[1,2-a]indole-5-carboxylate 在 4-二甲氨基吡啶 、 间氯过氧苯甲酸 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 methyl (1aS,8R,8aS,8bS)-1,1a,2,8,8a,8b-hexahydro-8-[(acetyloxy)methyl]-7-(benzyloxy)-1-(tert-butyloxycarbonyl)-8-formylazirino[2',3':3,4]pyrrolo[1,2-a]indole-5-carboxylate 3-oxide
  参考文献：
  名称：

  Chiral Aziridinyl Radicals:  An Application to the Synthesis of the Core Nucleus of FR-900482

  摘要：

  An asymmetric route to the core nucleus of the antitumor agent FR-900482 utilizes the cyclization of an aziridinyl radical into a functionalized indole nucleus. The route employs a selective Polonovski reaction and the Hootele-Dmitrienko rearrangement to install two oxygen atoms.

  DOI：

  10.1021/jo961992n