5-chloro-4-trifluoromethyl-2,6-diphenylpyrimidine | 960161-31-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-chloro-4-trifluoromethyl-2,6-diphenylpyrimidine
• 英文别名: 5-Chloro-2,4-diphenyl-6-(trifluoromethyl)pyrimidine
• CAS: 960161-31-3
• 化学式: C₁₇H₁₀ClF₃N₂
• 分子量: 334.728
• InChiKey: KTALNXPLLNPFHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-chloro-4-trifluoromethyl-2,6-diphenylpyrimidine 、 三丁基-[4-(三氟甲基)苯基]锡烷 在 四(三苯基膦)钯 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以98%的产率得到
  参考文献：
  名称：

  One pot synthesis of novel α,β-dichloro-β-trifluoromethylated enones and their application to the synthesis of trifluoromethylated heterocycles

  摘要：

  Trifluoropropynyllithium was reacted with 1 equiv of Weinreb benzamides in THF at -78 to 0 degrees C followed by treatment with 4 equiv of trifluoromethanesulfonyl chloride to give alpha,beta-dichloro-beta-trifluoromethylated enones 1 in 61-68% yield. The reactions of 1a with substituted amidines or hydrazines in refluxing 1,4-dioxane-CH3CN afforded trifluoromethylated chloropyrimidines 3 and chloropyrazoles 6 in 58-98% yields. The microwave-assisted coupling reactions of 3 with substituted phenylstannane and allylstannane in refluxing CH3CN in the presence of Pd(PPh3)(4) provided the corresponding phenyl and allyl substituted pyrimidines 4 in 89-98% yields. (c) 2006 Published by Elsevier B.V.

  DOI：

  10.1016/j.jfluchem.2006.11.003
• 作为产物：
  描述：

  2,3-dichloro-4,4,4-trifluoro-1-phenyl-2-buten-1-one 、 苄脒盐酸盐 在 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 12.0h， 以95%的产率得到5-chloro-4-trifluoromethyl-2,6-diphenylpyrimidine
  参考文献：
  名称：

  One pot synthesis of novel α,β-dichloro-β-trifluoromethylated enones and their application to the synthesis of trifluoromethylated heterocycles

  摘要：

  Trifluoropropynyllithium was reacted with 1 equiv of Weinreb benzamides in THF at -78 to 0 degrees C followed by treatment with 4 equiv of trifluoromethanesulfonyl chloride to give alpha,beta-dichloro-beta-trifluoromethylated enones 1 in 61-68% yield. The reactions of 1a with substituted amidines or hydrazines in refluxing 1,4-dioxane-CH3CN afforded trifluoromethylated chloropyrimidines 3 and chloropyrazoles 6 in 58-98% yields. The microwave-assisted coupling reactions of 3 with substituted phenylstannane and allylstannane in refluxing CH3CN in the presence of Pd(PPh3)(4) provided the corresponding phenyl and allyl substituted pyrimidines 4 in 89-98% yields. (c) 2006 Published by Elsevier B.V.

  DOI：

  10.1016/j.jfluchem.2006.11.003