5-cyano-6-phenyl-1,2,4-triazine | 190711-23-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 5-cyano-6-phenyl-1,2,4-triazine
• 英文别名: 6-Phenyl-1,2,4-triazine-5-carbonitrile
• CAS: 190711-23-0
• 化学式: C₁₀H₆N₄
• 分子量: 182.184
• InChiKey: WSHBFNUXENESLI-UHFFFAOYSA-N

物化性质

• 沸点：
  447.6±47.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• 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：

  5-cyano-6-phenyl-1,2,4-triazine 在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 2,4-diacetyl-3-(1H-indol-3-yl)-6-phenyl-3,4-dihydro-2H-[1,2,4]triazin-5-one
  参考文献：
  名称：

  吖嗪酮与 C-亲核试剂反应中的不对称诱导

  摘要：

  研究了酰化剂对 C-亲核试剂添加到 1,2,4-和 1,3,5-三嗪酮以及喹喔啉-2(1H)-one 过程中的影响。获得了一系列新的吖嗪酮衍生物。提出了一种在 N-Ts-L-氨基酸酰氯存在下制备吲哚到 1,2,4-三嗪酮和喹喔啉-2(1H)-one 的非对映异构纯加成产物的方法。

  DOI：

  10.1007/s11172-010-0195-z
• 作为产物：
  描述：

  丙酮氰醇 、 6-Phenyl-1,2,4-triazine N-oxide 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以75%的产率得到5-cyano-6-phenyl-1,2,4-triazine
  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

文献信息

• The amidine rearrangement in 5-amino-6-aryl-1,2,4-triazine-4-oxides initiated by hydroxylamine
  作者：Oleg N Chupakhin、Valery N Kozhevnikov、Anton M Prokhorov、Dmitry N Kozhevnikov、Vladimir L Rusinov

  DOI：10.1016/s0040-4039(00)01245-4

  日期：2000.9

  Addition of hydroxylamine at the 3 position of 6-aryl-5-amino-1,2,4-triazine-4-oxides initiates the amidine rearrangement resulting in 6-aryl-5-hydroxylamine-1,2,4-triazines, as confirmed by an experiment with N-15-labeling. (C) 2000 Published by Elsevier Science Ltd.
• ——
  作者：D. N. Kozhevnikov、V. N. Kozhevnikov、I. S. Kovalev、V. L. Rusinov、O. N. Chupakhin、G. G. Aleksandrov

  DOI：10.1023/a:1019631610505

  日期：——

  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.
• Asymmetric induction in the reactions of azinones with C-nucleophiles
  作者：O. N. Chupakhin、I. N. Egorov、V. L. Rusinov、P. A. Slepukhin

  DOI：10.1007/s11172-010-0195-z

  日期：2010.5

  acylating agents on the course of addition of C-nucleophiles to 1,2,4- and 1,3,5-triazinones, as well as to quinoxalin-2(1H)-one, was studied. A series of new azinone derivatives was obtained. A method for the preparation of diastereomerically pure addition products of indoles to 1,2,4-triazinones and quinoxalin-2(1H)-one in the presence of N-Ts-L-amino acid acyl chlorides was suggested.

  研究了酰化剂对 C-亲核试剂添加到 1,2,4-和 1,3,5-三嗪酮以及喹喔啉-2(1H)-one 过程中的影响。获得了一系列新的吖嗪酮衍生物。提出了一种在 N-Ts-L-氨基酸酰氯存在下制备吲哚到 1,2,4-三嗪酮和喹喔啉-2(1H)-one 的非对映异构纯加成产物的方法。