2-{3-[(E)-2-(1H-Indol-3-yl)-vinyl]-5,5-dimethyl-cyclohex-2-enylidene}-malononitrile | 27334-35-6

• 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: 2-{3-[(E)-2-(1H-Indol-3-yl)-vinyl]-5,5-dimethyl-cyclohex-2-enylidene}-malononitrile
• CAS: 27334-35-6
• 化学式: C₂₁H₁₉N₃
• 分子量: 313.402
• InChiKey: ZZILRZBEJDJEPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  63.37
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  3-吲哚甲醛 、 (3,5,5-三甲基环己-2-烯亚基)丙二腈 在 哌啶 作用下， 以 丙醇 为溶剂， 反应 10.0h， 以60%的产率得到2-{3-[(E)-2-(1H-Indol-3-yl)-vinyl]-5,5-dimethyl-cyclohex-2-enylidene}-malononitrile
  参考文献：
  名称：

  The synthesis and spectral properties of a stimuli-responsive D-π-A charge transfer dye

  摘要：

  A new donor-pi-acceptor (D-pi-A) type isophorone dye was synthesized by the condensation reaction between 2-(3,5,5-trimethylcyclohex-2-enylidene)-malononitrile and indole-3-carboxaldehyde. The chemical structure of the dye was characterized by H-1 NMR, EA and MS. A novel, chromogenic, fluorescent dye based on indol as donor unit and isophorone as acceptor unit displayed marked UV-visible absorption changes and highly selective fluorescence quenching in the presence of fluoride ion. The dye also exhibited sizeable colour changes when used as a pH-induced molecular switch and as a detector for volatile organic compounds. The absorption and fluorescent intensity of the dye can be reversibly selected by protonation/deprotonation of the amine moiety via control of intramolecular charge transfer (ICT), leading to a molecular switch with "on" and "off" states. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2010.09.027