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 | 187682-39-9

• 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,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
• 英文别名: 5-O-tert-butyl 12-O-methyl (4S,6R,7S,8R)-8-formyl-8-(hydroxymethyl)-10-phenylmethoxy-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),10,12-triene-5,12-dicarboxylate
• CAS: 187682-39-9
• 化学式: C₂₇H₃₀N₂O₇
• 分子量: 494.544
• InChiKey: RTGVNCYHRMRDSG-BHTAKDFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  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 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 乙酸酐 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 34.5h， 生成 methyl (1aS,8R,9S,9aS)-1,1a,2,8,9,9a-hexahydro-1-(tert-butyloxycarbonyl)-8-formyl-7,9-dihydroxy-8-(hydroxymethyl)-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)-8-(hydroxymethyl)-1-(tert-butyloxycarbonyl)azirino[2',3':3,4]pyrrolo[1,2-a]indole-5-carboxylate 在 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 2.75h， 生成 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
  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

文献信息

• Chiral Aziridinyl Radicals:  An Application to the Synthesis of the Core Nucleus of FR-900482
  作者：Frederick E. Ziegler、Makonen Belema

  DOI：10.1021/jo961992n

  日期：1997.2.1

  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.