2-Cyano-3-(4-hydroxy-phenyl)-but-2-enedinitrile | 72971-39-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-Cyano-3-(4-hydroxy-phenyl)-but-2-enedinitrile
• 英文别名: 2-(4-Hydroxyphenyl)ethene-1,1,2-tricarbonitrile
• CAS: 72971-39-2
• 化学式: C₁₁H₅N₃O
• 分子量: 195.18
• InChiKey: WLAVFLAVEPPVJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丙二腈 、 对苯醌 在 吡啶 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以39%的产率得到7,7-dicyanobenzoquinone methide
  参考文献：
  名称：

  New electron acceptors: synthesis, electrochemistry, and radical anions of N,7,7-tricyanoquinomethanimines and x-ray crystal structures of the trimethyl and tetramethyl derivatives

  摘要：

  The reaction of a range of quinones 3 with malononitrile in the presence of titanium tetrachloride/pyridine yields dicyanoquinomethides 4, which on reaction with N,N'-bis(trimethylsilyl)carbodiimide are converted into the corresponding N,7,7-tricyanoquinomethanimines 6. The solution electrochemical redox properties of compounds 6 have been studied by cyclic voltammetry; they are strong acceptors which readily form radical anions and dianions. The radical anions of N,7,7-tricyanoquinodimethanimine 6a and the tetra-, tri- and dimethyl derivatives 6c, 6d, and 6e, respectively, have been studied by ESR and ENDOR spectroscopy. X-ray crystal structure analysis reveals that trimethyl derivative 6d is planar, whereas the tetramethyl derivative 6c is strongly deformed with the ring existing in a boat conformation, similar to that found previously for tetrasubstituted TCNQ derivatives.

  DOI：

  10.1021/jo00032a017

文献信息

• New electron acceptors: synthesis, electrochemistry, and radical anions of N,7,7-tricyanoquinomethanimines and x-ray crystal structures of the trimethyl and tetramethyl derivatives
  作者：Martin R. Bryce、Stephen R. Davies、Andrew M. Grainger、Michael B. Hursthouse、Mohammed Mazid、Rainer Bachmann、Fabian Gerson、Jonas Hellberg

  DOI：10.1021/jo00032a017

  日期：1992.3

  The reaction of a range of quinones 3 with malononitrile in the presence of titanium tetrachloride/pyridine yields dicyanoquinomethides 4, which on reaction with N,N'-bis(trimethylsilyl)carbodiimide are converted into the corresponding N,7,7-tricyanoquinomethanimines 6. The solution electrochemical redox properties of compounds 6 have been studied by cyclic voltammetry; they are strong acceptors which readily form radical anions and dianions. The radical anions of N,7,7-tricyanoquinodimethanimine 6a and the tetra-, tri- and dimethyl derivatives 6c, 6d, and 6e, respectively, have been studied by ESR and ENDOR spectroscopy. X-ray crystal structure analysis reveals that trimethyl derivative 6d is planar, whereas the tetramethyl derivative 6c is strongly deformed with the ring existing in a boat conformation, similar to that found previously for tetrasubstituted TCNQ derivatives.