Methyl 4-phenyl-2-(trichloromethyl)pyrimidine-5-carboxylate | 143034-44-0

• 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 4-phenyl-2-(trichloromethyl)pyrimidine-5-carboxylate
• CAS: 143034-44-0
• 化学式: C₁₃H₉Cl₃N₂O₂
• 分子量: 331.586
• InChiKey: KMIZIKVDCILZMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  苯丙炔酸甲酯 、 4-Dimethylamino-2-trichloromethyl-1,3-diazabutadiene 以 甲苯 为溶剂， 反应 30.0h， 以51%的产率得到Methyl 4-phenyl-2-(trichloromethyl)pyrimidine-5-carboxylate
  参考文献：
  名称：

  1,3-Diaza-1,3-butadienes. Synthesis and Conversion into Pyrimidines by [4π + 2π] Cycloaddition with Electron Deficient Acetylenes. Synthetic Utility of 2-(Trichloromethyl)pyrimidines¹

  摘要：

  Methods have been devised to generate 1H-1,3-diaza-1,3-butadienes bearing a leaving group at position-4 in latent, masked, and unprotected forms. A hallmark of these azadienes is that they undergo thermal [4 pi + 2 pi] cycloaddition reactions with electron deficient acetylenes to give adducts which are aromatized to pyrimidine derivatives under the reaction conditions. Thus, 1-(methoxycarbonyl)-3-acylamidines 17 on beating in solution are converted in situ into the 1,3-diaza-1,3-dienes 18 and/or 19 which react with dimethyl acetylenedicarboxylate (DMAD) to produce the pyrimidines 20. The 1-Boc-1,3-diaza-1,3-dienes 24 are masked forms of the LH-dienes inasmuch as they react with DMAD under relatively mild conditions to give the dihydropyrimidine adducts 25, which are easily detectable by H-1 NMR spectroscopy, and which aromatize to pyrimidines 26 at higher temperatures. The 4-methylthio compounds 31 and 33, and the 2-(trichloromethyl) compounds 37, are isolable, relatively stable, 1H-1,3-diaza-1,3-butadienes, These easily prepared compounds react with electron deficient acetylenes under mild conditions to provide the pyrimidines 20, 34, and 38, respectively, in fair to excellent yields. The 2-(trichloromethyl)pyrimidines 38 are very useful precursors of a wide variety of other 2-substituted pyrimidines 46-52.

  DOI：

  10.1021/jo952106w

文献信息

• New [4 + 2] Heterocycloaddition of Alkynyl Fischer Carbene Complexes. A Facile Access to Pyrimidyl Carbene Complexes
  作者：José Barluenga、Luis A. López、Silvia Martínez、Miguel Tomás

  DOI：10.1055/s-1999-2573

  日期：1999.2

  Pyrimidyl carbene complexes 4 have been obtained by [4 + 2] cycloaddition of 1,3-diazadiene derivative 1 and alkynyl carbene complexes 2, 3. Compounds 4 are precursors of some indeno[1,2-d]pyrimidine and quinazoline derivatives.

  通过 1,3-二氮二烯衍生物 1 和炔基碳络合物 2、3 的[4 + 2]环加成，得到了嘧啶基碳络合物 4。化合物 4 是一些茚并[1,2-d]嘧啶和喹唑啉衍生物的前体。
• Synthesis of pyrimidines from 2-trichloromethyl-4-dimethylamino-1,3-diaza-1,3-butadienes and electron deficient acetylenes
  作者：Angel Guzmán、Moisés Romero、Francisco X. Talamás、Joseph M. Muchowski

  DOI：10.1016/s0040-4039(00)92660-1

  日期：1992.6

  2-Trichloromethyl-4-dimethylamino-1,3-diaza-1,3-butadienes(3), prepared from trichloroacetamidine(1) and amide acetals 2, readily react with electron deficient acetylenes 4 to give 2-trichloromethylpyrimidines 5.