4-[4-(2,6-diphenyl-pyran-4-ylidenemethyl)-phenylethynyl]-benzonitrile | 1450722-33-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[4-(2,6-diphenyl-pyran-4-ylidenemethyl)-phenylethynyl]-benzonitrile
• 英文别名: 4-[2-[4-[(2,6-Diphenylpyran-4-ylidene)methyl]phenyl]ethynyl]benzonitrile
• CAS: 1450722-33-4
• 化学式: C₃₃H₂₁NO
• 分子量: 447.536
• InChiKey: DKMGICLHYCVBQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[4-(2,6-diphenyl-pyran-4-ylidenemethyl)-phenylethynyl]-benzonitrile 在 碘 作用下， 以 二氯甲烷 为溶剂， 以45%的产率得到C₆₆H₄₀N₂O₂
  参考文献：
  名称：

  Methylenepyran based dipolar and quadrupolar dyes: synthesis, electrochemical and photochemical properties

  摘要：

  This paper presents the synthesis of a series of push-pull and quadrupolar pi-conjugated structures incorporating pro-aromatic methylenepyran electron-donor groups and various electron-attracting groups. Some of the methylenepyran derivatives were oxidized by I-2 to give, after reduction by Na2S2O3, bismethylenepyran compounds via successive steps.The electrochemical redox properties of methylenepyrans 5-9 and extended bismethylenepyrans 10, 14, and 15 determined by cyclic voltammetry indicate the formation of redox bistable systems with high bistability. Oxidation of the dimers obtained from 5 to 9 was also described. All compounds are colored and slightly fluorescent (except some bismethylenepyran derivatives). Some compound second-order nonlinear optical properties were investigated, and large positive values of mu beta were obtained. A positive dimer effect was also observed for bispyran derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.066
• 作为产物：
  描述：

  2,6-diphenyl-4H-pyran-4-yl triphenylphosphonium tetrafluoroborate salt 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 potassium carbonate 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 正戊烷 为溶剂， 反应 0.25h， 生成 4-[4-(2,6-diphenyl-pyran-4-ylidenemethyl)-phenylethynyl]-benzonitrile
  参考文献：
  名称：

  Methylenepyran based dipolar and quadrupolar dyes: synthesis, electrochemical and photochemical properties

  摘要：

  This paper presents the synthesis of a series of push-pull and quadrupolar pi-conjugated structures incorporating pro-aromatic methylenepyran electron-donor groups and various electron-attracting groups. Some of the methylenepyran derivatives were oxidized by I-2 to give, after reduction by Na2S2O3, bismethylenepyran compounds via successive steps.The electrochemical redox properties of methylenepyrans 5-9 and extended bismethylenepyrans 10, 14, and 15 determined by cyclic voltammetry indicate the formation of redox bistable systems with high bistability. Oxidation of the dimers obtained from 5 to 9 was also described. All compounds are colored and slightly fluorescent (except some bismethylenepyran derivatives). Some compound second-order nonlinear optical properties were investigated, and large positive values of mu beta were obtained. A positive dimer effect was also observed for bispyran derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.066