methyl 2-(cyclohexenylethynyl)-4-methyl-6-phenylpyrimidine-5-carboxylate | 1227077-11-3

• 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: methyl 2-(cyclohexenylethynyl)-4-methyl-6-phenylpyrimidine-5-carboxylate
• 英文别名: Methyl 2-[2-(cyclohexen-1-yl)ethynyl]-4-methyl-6-phenylpyrimidine-5-carboxylate；methyl 2-[2-(cyclohexen-1-yl)ethynyl]-4-methyl-6-phenylpyrimidine-5-carboxylate
• CAS: 1227077-11-3
• 化学式: C₂₁H₂₀N₂O₂
• 分子量: 332.402
• InChiKey: WWJWSMFDFORCMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-甲基-2-氧代-4-苯基-1,2-二氢嘧啶-5-羧酸甲酯 、 1-乙炔基环己烷 在 三乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 、 双(乙腈)氯化钯(II) 、 caesium carbonate 、 2-(二环己基膦基)联苯 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以76%的产率得到methyl 2-(cyclohexenylethynyl)-4-methyl-6-phenylpyrimidine-5-carboxylate
  参考文献：
  名称：

  Efficient Pd-Catalyzed Coupling of Tautomerizable Heterocycles with Terminal Alkynes via C−OH Bond Activation Using PyBrOP

  摘要：

  The direct alkynylation of tautomerizable heterocycles is described via a two-step process involving in situ C OH activation with bromotripyrrolidinophosphonium hexafluorophosphate (PyBrOP) followed by Sonogashira coupling with a wide range of alkyl or aryl terminal alkynes using a copper-free system employing PdCl2(CH3CN)(2) and 2-(dicyclohexylphosphino)biphenyl.

  DOI：

  10.1021/ol100657n

文献信息

• Efficient Pd-Catalyzed Coupling of Tautomerizable Heterocycles with Terminal Alkynes via C−OH Bond Activation Using PyBrOP
  作者：Ce Shi、Courtney C. Aldrich

  DOI：10.1021/ol100657n

  日期：2010.5.21

  The direct alkynylation of tautomerizable heterocycles is described via a two-step process involving in situ C OH activation with bromotripyrrolidinophosphonium hexafluorophosphate (PyBrOP) followed by Sonogashira coupling with a wide range of alkyl or aryl terminal alkynes using a copper-free system employing PdCl2(CH3CN)(2) and 2-(dicyclohexylphosphino)biphenyl.