3-(4-Chloro-phenyl)-6-phenyl-[1,2,4]triazine-5-carbonitrile | 292850-42-1

• 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: 3-(4-Chloro-phenyl)-6-phenyl-[1,2,4]triazine-5-carbonitrile
• 英文别名: 3-(4-Chlorophenyl)-6-phenyl-1,2,4-triazine-5-carbonitrile
• CAS: 292850-42-1
• 化学式: C₁₆H₉ClN₄
• 分子量: 292.727
• InChiKey: VALRTBJSJCFYEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  丙二腈 、 3-(4-Chloro-phenyl)-6-phenyl-[1,2,4]triazine-5-carbonitrile 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.25h， 生成 3-(4-chlorophenyl)-5-dicyanomethylene-6-phenyl-4,5-dihydro-1,2,4-triazine
  参考文献：
  名称：

  摘要：

  Nucleophilic substitution of hydrogen in pyrazine N-oxides under the action of CH-active compounds requires activation with acylating agents. This activation facilitates aromatization of intermediate sigma(H) adducts via elimination of the acid residue to form substituted pyrazines. More electrophilic 1,2.4-triazine 4-oxides react with carbanions derived from CH-active compounds without additional activation according to a scheme, which has previously been unknown for azine N-oxides. This scheme involves aromatization of a H adducts through elimination of water by the E1cb mechanism. The reaction products occur in DMSO-d(6) Solutions predominantly as 6-methylene-1,6-dihydropyrazines and 5-methylene-4,5-dihydro-1,2,4-triazines.

  DOI：

  10.1023/a:1025601311393
• 作为产物：
  描述：

  丙酮氰醇 、 3-(4-chlorophenyl)-6-phenyl-1,2,4-triazin-4-ium-4-olate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以97%的产率得到3-(4-Chloro-phenyl)-6-phenyl-[1,2,4]triazine-5-carbonitrile
  参考文献：
  名称：

  摘要：

  The scope of functionalization of 1,2,4-triazines can be considerably extended via successive nucleophilic substitution of hydrogen (S-N(H)) and ipso-substitution. A convenient procedure has been developed for direct cyanation of 1,2,4-triazine 4-oxides with acetone cyanohydrin in the presence of triethylamine. The cyano group in the resulting 5-cyano-1,2,4-triazines is readily replaced by reactions with various aliphatic alcohols and amines.

  DOI：

  10.1023/a:1019631610505