4-Dicyanomethylene-2,6-dimethyl-2,5-cyclohexadiene-1-one | 95276-20-3

• 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: 4-Dicyanomethylene-2,6-dimethyl-2,5-cyclohexadiene-1-one
• 英文别名: 2-(3,5-Dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)propanedinitrile
• CAS: 95276-20-3
• 化学式: C₁₁H₈N₂O
• 分子量: 184.197
• InChiKey: ABPIJHRQNPPWPB-UHFFFAOYSA-N

物化性质

• 沸点：
  300.8±42.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Dicyanomethylene-2,6-dimethyl-2,5-cyclohexadiene-1-one 在 氢化钾 、 四氯化钛 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 40.0h， 生成
  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
• 作为产物：
  描述：

  2,6-dimethyl-4-(dicyanomethylene)cyclohexanone 在 吡啶 、 溴 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以59%的产率得到4-Dicyanomethylene-2,6-dimethyl-2,5-cyclohexadiene-1-one
  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

• N,7,7-tricyanoquinomethaneimines: new electron acceptors for organic metals
  作者：Martin R. Bryce、Stephen R. Davies

  DOI：10.1039/c39890000328

  日期：——

  Four derivatives of the title system, which is a new class of electron acceptor, have been synthesised; cyclic voltammetric data show that these compounds undergo one- and two-electron reductions.

  已经合成了标题系统的四种衍生物，这是一类新的电子受体。循环伏安数据表明，这些化合物经历了一电子和二电子还原。
• FACILE SYNTHESES OF<i>P</i>-(DICYANOMETHYLENE)BENZOQUINONES
  作者：Masato Nanasawa、Hiroshi Takahashi、Tetsuo Kuwabara

  DOI：10.1080/00304949809355264

  日期：1998.2
• 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.