methyl (1aS,9R,9aS)-4,7-bis(benzyloxy)-9-hydroxy-6-methoxy-5-methyl-8-methylene-1a,2,3,8,9,9a-hexahydro-1H-azirino[2,3-f]benzo[b]azocine-1-carboxylate | 1175522-80-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl (1aS,9R,9aS)-4,7-bis(benzyloxy)-9-hydroxy-6-methoxy-5-methyl-8-methylene-1a,2,3,8,9,9a-hexahydro-1H-azirino[2,3-f]benzo[b]azocine-1-carboxylate
• 英文别名: methyl (4S,6S,7R)-7-hydroxy-11-methoxy-12-methyl-8-methylidene-10,13-bis(phenylmethoxy)-2,5-diazatricyclo[7.4.0.04,6]trideca-1(9),10,12-triene-5-carboxylate
• CAS: 1175522-80-1
• 化学式: C₃₀H₃₂N₂O₆
• 分子量: 516.594
• InChiKey: ZEYJUFILARTTMA-KONZJBAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  89.3
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl (2S,3R)-2-((R)-2-(2,5-bis(benzyloxy)-3-methoxy-4-methyl-6-nitrophenyl)-1-hydroxyallyl)-3-((methylsulfonyloxy)methyl)aziridine-1-carboxylate 在 氯化铵 、 锌 作用下， 以 水 、 丙酮 为溶剂， 反应 3.0h， 以99%的产率得到methyl (1aS,9R,9aS)-4,7-bis(benzyloxy)-9-hydroxy-6-methoxy-5-methyl-8-methylene-1a,2,3,8,9,9a-hexahydro-1H-azirino[2,3-f]benzo[b]azocine-1-carboxylate
  参考文献：
  名称：

  Synthetic studies toward the mitomycins: construction of the tetracyclic core via a reductive aminocyclization reaction

  摘要：

  The tetracyclic core of the mitomycin family of natural products has been formed in one step from an acyclic precursor via a reductive aminocyclization reaction. Additionally, the eight-membered benzazocine can be prepared without the need for prior activation of the aniline. Construction of a mitomycin K analogue lacking the C9a methoxy moiety is also reported herein. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.05.004

文献信息

• Synthetic studies toward the mitomycins: construction of the tetracyclic core via a reductive aminocyclization reaction
  作者：Daniel A. Gubler、Robert M. Williams

  DOI：10.1016/j.tetlet.2009.05.004

  日期：2009.7

  The tetracyclic core of the mitomycin family of natural products has been formed in one step from an acyclic precursor via a reductive aminocyclization reaction. Additionally, the eight-membered benzazocine can be prepared without the need for prior activation of the aniline. Construction of a mitomycin K analogue lacking the C9a methoxy moiety is also reported herein. (C) 2009 Elsevier Ltd. All rights reserved.