2,2'-bis(chlorocyanomethyl)biphenyl | 289673-79-6

• 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: 2,2'-bis(chlorocyanomethyl)biphenyl
• 英文别名: 2-Chloro-2-[2-[2-[chloro(dicyano)methyl]phenyl]phenyl]propanedinitrile
• CAS: 289673-79-6
• 化学式: C₁₈H₈Cl₂N₄
• 分子量: 351.194
• InChiKey: ADZLPHYDPHDWOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  95.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2'-bis(chlorocyanomethyl)biphenyl 在 锌 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以70%的产率得到9,9,10,10-tetracyano-9,10-dihydrophenanthrene
  参考文献：
  名称：

  Preparation and Molecular Structures of 9,10-Dihydrophenanthrenes:  Substituent Effects on the Long Bond Length

  摘要：

  9,10-Dihydrophenanthrene derivatives 1-3 with electron-donating and/or -accepting groups at their 9,10-positions were prepared, and their precise molecular structures were determined by X-ray analyses at 203 K. The long C-9-C-10 bond [1.646(4) Angstrom] in the hexaarylethane-type compound 1 with four electron-donating groups is mainly caused by steric interaction. Push-pull type substitution does not induce the elongation of the central bond in the present system; the corresponding distance in 9,9-bis(4-dimethylaminophenyl)-10,10-dicyano derivative 2 [1.599(4) Angstrom] is intermediate between those of 1 and the tetracyano compound 3 [1.587(2) Angstrom].

  DOI：

  10.1021/jo0003697
• 作为产物：
  描述：

  2,2-二碘代联苯 在 N-氯代丁二酰亚胺 、 四(三苯基膦)钯 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 83.0h， 生成 2,2'-bis(chlorocyanomethyl)biphenyl
  参考文献：
  名称：

  Preparation and Molecular Structures of 9,10-Dihydrophenanthrenes:  Substituent Effects on the Long Bond Length

  摘要：

  9,10-Dihydrophenanthrene derivatives 1-3 with electron-donating and/or -accepting groups at their 9,10-positions were prepared, and their precise molecular structures were determined by X-ray analyses at 203 K. The long C-9-C-10 bond [1.646(4) Angstrom] in the hexaarylethane-type compound 1 with four electron-donating groups is mainly caused by steric interaction. Push-pull type substitution does not induce the elongation of the central bond in the present system; the corresponding distance in 9,9-bis(4-dimethylaminophenyl)-10,10-dicyano derivative 2 [1.599(4) Angstrom] is intermediate between those of 1 and the tetracyano compound 3 [1.587(2) Angstrom].

  DOI：

  10.1021/jo0003697

文献信息

• Preparation and Molecular Structures of 9,10-Dihydrophenanthrenes:  Substituent Effects on the Long Bond Length
  作者：Takanori Suzuki、Kazunori Ono、Jun-ichi Nishida、Hyou Takahashi、Takashi Tsuji

  DOI：10.1021/jo0003697

  日期：2000.8.1

  9,10-Dihydrophenanthrene derivatives 1-3 with electron-donating and/or -accepting groups at their 9,10-positions were prepared, and their precise molecular structures were determined by X-ray analyses at 203 K. The long C-9-C-10 bond [1.646(4) Angstrom] in the hexaarylethane-type compound 1 with four electron-donating groups is mainly caused by steric interaction. Push-pull type substitution does not induce the elongation of the central bond in the present system; the corresponding distance in 9,9-bis(4-dimethylaminophenyl)-10,10-dicyano derivative 2 [1.599(4) Angstrom] is intermediate between those of 1 and the tetracyano compound 3 [1.587(2) Angstrom].