(rac)-3-keto-α-ionylideneacetonitrile | 249306-13-6

• 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: (rac)-3-keto-α-ionylideneacetonitrile
• 英文别名: (4E)-3-methyl-5-(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)penta-2,4-dienenitrile
• CAS: 249306-13-6
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: WLVJUFWJOCVQKX-QCJYOOBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (rac)-3-keto-α-ionylideneacetonitrile 在 二异丁基氢化铝 作用下， 以 甲醇 为溶剂， 生成 (2E,4E)-5-(4-Methoxy-2,6,6-trimethyl-cyclohexa-1,3-dienyl)-3-methyl-penta-2,4-dienal
  参考文献：
  名称：

  Probing for the Threshold Energy for Visual Transduction: Red-Shifted Visual Pigment Analogs from 3-Methoxy-3-Dehydroretinal and Related Compounds

  摘要：

  Abstract— While azulenic retinal analogs failed to yield a red‐shifted visual pigment analog, the 9‐cis isomers of the push‐pull polyenals 3‐methoxy‐3‐dehydroretinal and 14F‐3‐me‐thoxy‐3‐dehydroretinal yielded iodopsin pigment analogs with absorption maxima at, respectively, 663 and 720 nm. The former gave a relatively stable batho product (700 nm) and was able to activate transducin. A lower activity was observed for the latter. One possible explanation for the combined results is that the excitation energies of these red‐shifted pigments are approaching the threshold energy for visual transduction (although at this time we cannot rigorously exclude a role of the added F‐atom in reducing the transducin activity).

  DOI：

  10.1111/j.1751-1097.1999.tb01956.x
• 作为产物：
  描述：

  氰甲基磷酸二乙酯 、 3-氧代-a-紫罗兰酮 在 sodium hydride 作用下， 以86%的产率得到(rac)-3-keto-α-ionylideneacetonitrile
  参考文献：
  名称：

  Probing for the Threshold Energy for Visual Transduction: Red-Shifted Visual Pigment Analogs from 3-Methoxy-3-Dehydroretinal and Related Compounds

  摘要：

  Abstract— While azulenic retinal analogs failed to yield a red‐shifted visual pigment analog, the 9‐cis isomers of the push‐pull polyenals 3‐methoxy‐3‐dehydroretinal and 14F‐3‐me‐thoxy‐3‐dehydroretinal yielded iodopsin pigment analogs with absorption maxima at, respectively, 663 and 720 nm. The former gave a relatively stable batho product (700 nm) and was able to activate transducin. A lower activity was observed for the latter. One possible explanation for the combined results is that the excitation energies of these red‐shifted pigments are approaching the threshold energy for visual transduction (although at this time we cannot rigorously exclude a role of the added F‐atom in reducing the transducin activity).

  DOI：

  10.1111/j.1751-1097.1999.tb01956.x