3-<(1R,S)-<(3E,7E)-10-(2,6,6-trimethyl-1-cyclohexen-1-yl)-8-methyl-4-hydroxymethyl-1-hydroxy>-3,7-decadien-1-yl>furan | 160084-21-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-<(1R,S)-<(3E,7E)-10-(2,6,6-trimethyl-1-cyclohexen-1-yl)-8-methyl-4-hydroxymethyl-1-hydroxy>-3,7-decadien-1-yl>furan
• 英文别名: (E)-5-(furan-3-yl)-2-[(E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hex-3-enyl]pent-2-ene-1,5-diol
• CAS: 160084-21-9
• 化学式: C₂₅H₃₈O₃
• 分子量: 386.575
• InChiKey: QUOGWFXSTXSXMF-KRDHTCMFSA-N

物化性质

• 沸点：
  459.6±45.0 °C(predicted)
• 密度：
  1.009±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  53.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-<(1R,S)-<(3E,7E)-10-(2,6,6-trimethyl-1-cyclohexen-1-yl)-8-methyl-4-hydroxymethyl-1-hydroxy>-3,7-decadien-1-yl>furan 在 四丙基高钌酸铵 、 3 A molecular sieve 、 氧气 、 rose bengal 、 N-甲基吗啉氧化物 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 8.0h， 生成 5-Hydroxy-4-{6-hydroxy-5-[(E)-4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hex-3-enyl]-3,6-dihydro-2H-pyran-2-yl}-5H-furan-2-one
  参考文献：
  名称：

  Two syntheses of manoalide via heteroatom-assisted alkyne carbometallation

  摘要：

  Two approaches to the sesterterpenoid phospholipase A(2) inhibitors seco-manoalide (3) and manoalide (1) are described based on carbometallation of propargylic alcohols to generate the functionalised C6-C7 trisubstituted alkene. Both syntheses also deploy the photooxidation of a furan in order to generate a 4-substituted-5-hydroxy-2(5H)-furanone moiety.

  DOI：

  10.1016/s0040-4020(01)85353-9
• 作为产物：
  描述：

  3-糠醛 在 正丁基锂 、 乙基溴化镁 、 ammonium chloride 作用下， 以 四氢呋喃 、 乙醚 、 异丙醚 、 苯 为溶剂， 反应 123.0h， 生成 3-<(1R,S)-<(3E,7E)-10-(2,6,6-trimethyl-1-cyclohexen-1-yl)-8-methyl-4-hydroxymethyl-1-hydroxy>-3,7-decadien-1-yl>furan
  参考文献：
  名称：

  Two syntheses of manoalide via heteroatom-assisted alkyne carbometallation

  摘要：

  Two approaches to the sesterterpenoid phospholipase A(2) inhibitors seco-manoalide (3) and manoalide (1) are described based on carbometallation of propargylic alcohols to generate the functionalised C6-C7 trisubstituted alkene. Both syntheses also deploy the photooxidation of a furan in order to generate a 4-substituted-5-hydroxy-2(5H)-furanone moiety.

  DOI：

  10.1016/s0040-4020(01)85353-9

文献信息

• Two syntheses of manoalide via heteroatom-assisted alkyne carbometallation
  作者：Paul Bury、Georges Hareau、Philip Kocieński、Dashyant Dhanak

  DOI：10.1016/s0040-4020(01)85353-9

  日期：1994.1

  Two approaches to the sesterterpenoid phospholipase A(2) inhibitors seco-manoalide (3) and manoalide (1) are described based on carbometallation of propargylic alcohols to generate the functionalised C6-C7 trisubstituted alkene. Both syntheses also deploy the photooxidation of a furan in order to generate a 4-substituted-5-hydroxy-2(5H)-furanone moiety.