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 | 187682-53-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 1-羟基氨基，4-未取代的苯类化合物
• 英文名称: 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
• 英文别名: 11-O-tert-butyl 4-O-methyl (8R,9S,10S,12S)-8-formyl-6,9-dihydroxy-8-(hydroxymethyl)-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2(7),3,5-triene-4,11-dicarboxylate
• CAS: 187682-53-7
• 化学式: C₂₀H₂₄N₂O₉
• 分子量: 436.419
• InChiKey: CMFHZTPACHGRCP-RCJNOXTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  146
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  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 在 Wilkinson's catalyst 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 xylene 为溶剂， 反应 4.08h， 生成 methyl (4aR,10aS,11aS,11bS)-4,4a,10,10a,11,11b-hexahydro-11-(tert-butyloxycarbonyl)-5-hydroxy-2,2-dimethyl-9,11b-epoxyazirino[2,3-c]-1,3-dioxino[4,5-e][1]benzazocine-7-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 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

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.