ethyl (E)-3-[2,5-bis(phenylmethoxy)phenyl]but-2-enoate | 131636-93-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl (E)-3-[2,5-bis(phenylmethoxy)phenyl]but-2-enoate
• CAS: 131636-93-6
• 化学式: C₂₆H₂₆O₄
• 分子量: 402.49
• InChiKey: LWIBPOCIMSZVBX-CAPFRKAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (E)-3-[2,5-bis(phenylmethoxy)phenyl]but-2-enoate 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 反应 36.0h， 以44%的产率得到(2R,3S)-3-(2,5-Bis-benzyloxy-phenyl)-2,3-dihydroxy-butyric acid ethyl ester
  参考文献：
  名称：

  A nitrone-based cycloaddition approach to the synthesis of the glycosyl system of nogalomycin, menogaril, and their congeners

  摘要：

  A series of model systems for the benzoxocin portion of nogalomycin was synthesized by cycloaddition of nitrone 8 with assorted dipolarophiles. Cycloaddition between nitrone 8 and vinyltrimethylsilane afforded isoxazolidines which were fragmented to produce either benzoxocins 21 and 23 or tricyclic isomer 27. Tricyclic systems 23 and 27 were produced also from the adduct of nitrone 8 and allyltrimethylsilane following fragmentation and oxidative cleavage of the resulting homoallylic amine derivative. Dipolar cycloaddition between nitrone 8 and vinylene carbonate yielded two diastereomeric isoxazolidines 40 and 41, both of which had the intact carbon skeleton of the glycosyl region of nogalomycin but which bore the incorrect relative configuration for transformation to menogaril analogue 5.

  DOI：

  10.1021/jo00004a008
• 作为产物：
  描述：

  2,5-二羟基苯乙酮 在 potassium tert-butylate 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 29.0h， 生成 ethyl (E)-3-[2,5-bis(phenylmethoxy)phenyl]but-2-enoate
  参考文献：
  名称：

  A nitrone-based cycloaddition approach to the synthesis of the glycosyl system of nogalomycin, menogaril, and their congeners

  摘要：

  A series of model systems for the benzoxocin portion of nogalomycin was synthesized by cycloaddition of nitrone 8 with assorted dipolarophiles. Cycloaddition between nitrone 8 and vinyltrimethylsilane afforded isoxazolidines which were fragmented to produce either benzoxocins 21 and 23 or tricyclic isomer 27. Tricyclic systems 23 and 27 were produced also from the adduct of nitrone 8 and allyltrimethylsilane following fragmentation and oxidative cleavage of the resulting homoallylic amine derivative. Dipolar cycloaddition between nitrone 8 and vinylene carbonate yielded two diastereomeric isoxazolidines 40 and 41, both of which had the intact carbon skeleton of the glycosyl region of nogalomycin but which bore the incorrect relative configuration for transformation to menogaril analogue 5.

  DOI：

  10.1021/jo00004a008

文献信息

• DESHONG, PHILIP;LI, WEI;KENNINGTON, JOHN W. (JR);AMMON, HERMAN L.;LEGINUS+, J. ORG. CHEM., 56,(1991) N, C. 1364-1373
  作者：DESHONG, PHILIP、LI, WEI、KENNINGTON, JOHN W. (JR)、AMMON, HERMAN L.、LEGINUS+

  DOI：——

  日期：——
• A nitrone-based cycloaddition approach to the synthesis of the glycosyl system of nogalomycin, menogaril, and their congeners
  作者：Philip DeShong、Wei Li、John W. Kennington、Herman L. Ammon、Joseph M. Leginvs

  DOI：10.1021/jo00004a008

  日期：1991.2

  A series of model systems for the benzoxocin portion of nogalomycin was synthesized by cycloaddition of nitrone 8 with assorted dipolarophiles. Cycloaddition between nitrone 8 and vinyltrimethylsilane afforded isoxazolidines which were fragmented to produce either benzoxocins 21 and 23 or tricyclic isomer 27. Tricyclic systems 23 and 27 were produced also from the adduct of nitrone 8 and allyltrimethylsilane following fragmentation and oxidative cleavage of the resulting homoallylic amine derivative. Dipolar cycloaddition between nitrone 8 and vinylene carbonate yielded two diastereomeric isoxazolidines 40 and 41, both of which had the intact carbon skeleton of the glycosyl region of nogalomycin but which bore the incorrect relative configuration for transformation to menogaril analogue 5.