5-fluoro-6-(p-toluenesulphonyl)pyrimidin-4(3H)-one | 118988-01-5

• 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: 5-fluoro-6-(p-toluenesulphonyl)pyrimidin-4(3H)-one
• 英文别名: 5-fluoro-4-(4-methylphenyl)sulfonyl-1H-pyrimidin-6-one
• CAS: 118988-01-5
• 化学式: C₁₁H₉FN₂O₃S
• 分子量: 268.268
• InChiKey: VWWGKXWYENPISY-UHFFFAOYSA-N

物化性质

• 沸点：
  402.6±55.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  84
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-甲苯磺酰氰 、 isopropyl N-((Z)-1-((tert-butyldimethylsilyl)oxy)-2-fluorovinyl)formimidate 以 苯 为溶剂， 反应 1.0h， 以59%的产率得到5-fluoro-6-(p-toluenesulphonyl)pyrimidin-4(3H)-one
  参考文献：
  名称：

  A highly efficient multicomponent synthesis of pyridones and pyrimidones by a [2+2+2] strategy

  摘要：

  :The reaction of N-silylated iminoethers with 2-substituted acetyl chlorides yields activated 2-azadienes. These were shown to react with electron-deficient acetylenic dienophiles to yield pyridones. They also react with quinones to give the corresponding aromatized cycloadducts in good yields. The reaction of a-azadienes with activated nitriles provided a very practical route towards polysubstituted pyrimidones. A multicomponent protocol is reported which combines a N-t-butyldimethylsilyl iminoether, an acetyl chloride derivative and a dienophile in the presence of triethylamine without isolation of any intermediate. This provides an extremely practical and versatile route to various mono- and polycyclic azaaromatics with a predictable substitution pattern. Yields ranged from 43 % to 94 % for the complete sequence. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01149-1

文献信息

• A Diels-Alder route towards pyrimidin-4-ones
  作者：Ph. Bayard、F. Sainte、R. Beaudegnies、L. Ghosez

  DOI：10.1016/s0040-4039(00)82118-8

  日期：1988.1

  N-acylimidates are readily silylated with t-butyldimethylsilyl triflate in the presence of triethylamine to give 2-aza-1,3-dienes . These react with activated nitriles to yield pyrimidin-4-ones .

  在三乙胺的存在下，N-酰基酰亚胺易于用三氟甲磺酸叔丁基二甲基甲硅烷基硅烷基化，得到2-氮杂-1,3-二烯。它们与活化的腈反应生成嘧啶-4-酮。
• BAYARD, PH.;SAINTE, F.;BEAUDEGNIES, R.;GHOSEZ, L., TETRAHEDRON LETT., 29,(1988) N 31, C. 3799-3802
  作者：BAYARD, PH.、SAINTE, F.、BEAUDEGNIES, R.、GHOSEZ, L.

  DOI：——

  日期：——