(Z)-4-[(E)-1-Methyl-3-(2,6,6-trimethyl-cyclohex-1-enyl)-prop-2-en-(E)-ylidene]-cyclooct-2-enol | 148705-59-3

• 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: (Z)-4-[(E)-1-Methyl-3-(2,6,6-trimethyl-cyclohex-1-enyl)-prop-2-en-(E)-ylidene]-cyclooct-2-enol
• CAS: 148705-59-3
• 化学式: C₂₁H₃₂O
• 分子量: 300.484
• InChiKey: HFMGQJFOOXIYFW-CTJQYDGHSA-N

物化性质

• 沸点：
  438.4±24.0 °C(predicted)
• 密度：
  0.993±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.88
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (Z)-4-[(E)-1-Methyl-3-(2,6,6-trimethyl-cyclohex-1-enyl)-prop-2-en-(E)-ylidene]-cyclooct-2-enol 在 barium manganate 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以90%的产率得到(Z)-4-[(E)-1-Methyl-3-(2,6,6-trimethyl-cyclohex-1-enyl)-prop-2-en-(E)-ylidene]-cyclooct-2-enone
  参考文献：
  名称：

  Synthesis of retinals with eight- and nine-membered rings in the side chain. Models for rhodopsin photobleaching intermediates

  摘要：

  The triggering process of rhodopsin activation leading to visual transduction has remained a key problem in the chemistry of vision. In order to provide probes to explore this process, retinal analogs ret8 3 and ret9 4, with the 11-ene cis-locked by 8- and 9-membered rings, have been synthesized. These could lead to pigment analogs which might accomodate a transoid chromophore upon irradiation, thus providing unique models for rhodopsin activation studies. Enzyme assays and flash photolysis of rhodopsin analogs incorporating ret8 and other retinal analogs showed that the triggering process requires complete 11-cis to trans isomerization involving the entire polyene moiety. The syntheses of ret8 3 and ret9 4 double bond isomers are described.

  DOI：

  10.1021/jo00065a014
• 作为产物：
  描述：

  tert-Butyl-dimethyl-((Z)-(1R,2R)-2-phenylselanyl-cyclooct-3-enyloxy)-silane 在 重铬酸吡啶 、 potassium tert-butylate 、 四丁基氟化铵 、 双氧水 、 sodium hydride 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.58h， 生成 (Z)-4-[(E)-1-Methyl-3-(2,6,6-trimethyl-cyclohex-1-enyl)-prop-2-en-(E)-ylidene]-cyclooct-2-enol
  参考文献：
  名称：

  Synthesis of retinals with eight- and nine-membered rings in the side chain. Models for rhodopsin photobleaching intermediates

  摘要：

  The triggering process of rhodopsin activation leading to visual transduction has remained a key problem in the chemistry of vision. In order to provide probes to explore this process, retinal analogs ret8 3 and ret9 4, with the 11-ene cis-locked by 8- and 9-membered rings, have been synthesized. These could lead to pigment analogs which might accomodate a transoid chromophore upon irradiation, thus providing unique models for rhodopsin activation studies. Enzyme assays and flash photolysis of rhodopsin analogs incorporating ret8 and other retinal analogs showed that the triggering process requires complete 11-cis to trans isomerization involving the entire polyene moiety. The syntheses of ret8 3 and ret9 4 double bond isomers are described.

  DOI：

  10.1021/jo00065a014