((5-[4-(dimethylamino)phenyl]-2H-1,2,3-triazol-4-yl)methylidene)propanedinitrile | 1039827-28-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ((5-[4-(dimethylamino)phenyl]-2H-1,2,3-triazol-4-yl)methylidene)propanedinitrile
• CAS: 1039827-28-5
• 化学式: C₁₄H₁₂N₆
• 分子量: 264.289
• InChiKey: ONJXOGNGRWKWDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  92.39
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-(3-(4-(dimethylamino)phenyl)prop-2-yn-1-ylidene)malononitrile 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以61%的产率得到((5-[4-(dimethylamino)phenyl]-2H-1,2,3-triazol-4-yl)methylidene)propanedinitrile
  参考文献：
  名称：

  1,2,3-Triazoles as Conjugative π-Linkers in Push−Pull Chromophores: Importance of Substituent Positioning on Intramolecular Charge-Transfer

  摘要：

  Isomeric charge-transfer chromophores using 1,2,3-triazol-diyl as linker have been studied experimentally and computationally. The instability of the polarized reactants precluded the use of the Huisgen reaction and alternative synthetic methodologies were employed. Charge-transfer absorptions between an N,N-dimethylanilino and a dicyanovinyl group are modest to strong, with maxima from lambda(max) = 400 to 453 nm depending on substituent positioning. TD-B3LYP/6-31G(d) calculations are within 0.6 eV of experiment and assign these bands as HOMO-LUMO transitions.

  DOI：

  10.1021/ol801253z