2-Cyano-3-(10-hydroxy-2,3,7,8-tetrahydro-benzo[1,2-b;4,5-b']bis[1,4]dithiin-5-yl)-but-2-enedinitrile | 138385-51-0

• 英文名称: 2-Cyano-3-(10-hydroxy-2,3,7,8-tetrahydro-benzo[1,2-b;4,5-b']bis[1,4]dithiin-5-yl)-but-2-enedinitrile
• CAS: 138385-51-0
• 化学式: C₁₅H₉N₃OS₄
• 分子量: 375.52
• InChiKey: KXGOMZDNVULTTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  91.6
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  2,3,7,8-tetrahydrobenzo[1,2-b:4,5-b']bis[1,4]dithiin-5,10-dione 、 丙二腈 在 吡啶 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以34%的产率得到2-(10-Oxo-2,3,7,8-tetrahydro-10H-benzo[1,2-b;4,5-b']bis[1,4]dithiin-5-ylidene)-malononitrile
  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