3-Hydroxysoraphen-2-ene

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: 3-Hydroxysoraphen-2-ene
• 英文别名: (3Z,5R,6S,7R,9S,10E,12R,13S,18S)-4,6,8-trihydroxy-5,12,13-trimethoxy-3,7,9-trimethyl-18-phenyl-1-oxacyclooctadeca-3,10-dien-2-one
• 化学式: C₂₉H₄₄O₈
• 分子量: 520.664
• InChiKey: FFLUEGLBLXLKOC-XRDGMINISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-methoxybenzenediazonium tetrafluoroborate 、 3-Hydroxysoraphen-2-ene 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 以100%的产率得到2,3-Dioxo-2,3-seco-soraphen-2-(4'-methoxyphenyl)hydrazone
  参考文献：
  名称：

  Synthesis of Southern-Part Models of Soraphen A

  摘要：

  A number of model compounds corresponding to substructures of the fungicidal macrolide soraphen A were prepared from the lactone 3. This lactone was obtained degradatively from soraphen A using the mild Japp-Klingemann variant of the retro-aldol reaction and ozonolysis of the double bond. Addition of ester enolates,ta the lactone 3 led to the isolation of unstable hemiacetals which were converted to their anomerically stabilized tautomers on chromatography or prolonged standing in solution. Because of the unusual stability of the initially formed hemiacetals it was possible to define the structures of the transition states of the addition of enolates to a lactone in unprecedented detail.

  DOI：

  10.1021/jo00109a028
• 作为产物：
  描述：

  3,5,7-O-Tris(trimethylsilyl)soraphen-2-ene 在 草酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以98%的产率得到3-Hydroxysoraphen-2-ene
  参考文献：
  名称：

  Synthesis of Southern-Part Models of Soraphen A

  摘要：

  A number of model compounds corresponding to substructures of the fungicidal macrolide soraphen A were prepared from the lactone 3. This lactone was obtained degradatively from soraphen A using the mild Japp-Klingemann variant of the retro-aldol reaction and ozonolysis of the double bond. Addition of ester enolates,ta the lactone 3 led to the isolation of unstable hemiacetals which were converted to their anomerically stabilized tautomers on chromatography or prolonged standing in solution. Because of the unusual stability of the initially formed hemiacetals it was possible to define the structures of the transition states of the addition of enolates to a lactone in unprecedented detail.

  DOI：

  10.1021/jo00109a028

文献信息

• Synthesis of Southern-Part Models of Soraphen A
  作者：Bernard Loubinoux、Jean-Luc Sinnes、Anthony C. O'Sullivan、Tammo Winkler

  DOI：10.1021/jo00109a028

  日期：1995.2

  A number of model compounds corresponding to substructures of the fungicidal macrolide soraphen A were prepared from the lactone 3. This lactone was obtained degradatively from soraphen A using the mild Japp-Klingemann variant of the retro-aldol reaction and ozonolysis of the double bond. Addition of ester enolates,ta the lactone 3 led to the isolation of unstable hemiacetals which were converted to their anomerically stabilized tautomers on chromatography or prolonged standing in solution. Because of the unusual stability of the initially formed hemiacetals it was possible to define the structures of the transition states of the addition of enolates to a lactone in unprecedented detail.