2-cyano-N-(2,6-dimethoxypyrimidin-4-yl)acetamide | 1067232-87-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-cyano-N-(2,6-dimethoxypyrimidin-4-yl)acetamide
• CAS: 1067232-87-4
• 化学式: C₉H₁₀N₄O₃
• 分子量: 222.203
• InChiKey: JVTQSFWZVSHACT-UHFFFAOYSA-N

物化性质

• 熔点：
  209-211 °C(Solvent: Ethanol)
• 密度：
  1.331±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  97.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-cyano-N-(2,6-dimethoxypyrimidin-4-yl)acetamide 、 对甲基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以82%的产率得到2-cyano-N-(2,6-dimethoxypyrimidin-4-yl)-3-(p-tolyl)acrylamide
  参考文献：
  名称：

  5-Cyanoacetylpyrimidines as intermediates for 7-aryl-6-cyanopyrido[2,3-d]pyrimidin-5-ones

  摘要：

  The reactions of N-4- and 5-cyanoacetyl derivates of 4-aminopyrimidines with aromatic aldehydes have yielded the N-(pyrimidin-4-yl)-3-arylacrylamides and the dihydropyrido[2,3-d]pyrimidines, respectively. The first reaction was a Claisen-Schmidt reaction catalysed by base, and the second one proceeded via thermal cyclocondensation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.08.070
• 作为产物：
  描述：

  4-氨基-2,6-二甲氧基嘧啶 、 氰乙酸 在 乙酸酐 作用下， 反应 0.17h， 以80%的产率得到2-cyano-N-(2,6-dimethoxypyrimidin-4-yl)acetamide
  参考文献：
  名称：

  用氰基乙酸和乙酸酐对6-氨基嘧啶进行C-和N-氰基乙酰化

  摘要：

  用氰基乙酸和乙酸酐的混合物将一系列6-氨基嘧啶氰基乙酰化。当使用嘧啶-4（3 H）-1作为底物时，取代发生在C-5，但是，当底物在C-2和C-4处被取代的嘧啶时，氰基乙酰化发生在环外氨基上。

  DOI：

  10.1016/j.tetlet.2008.07.084

文献信息

• 2-Cyano-<i>N</i>-(2,6-dimethoxypyrimidin-4-yl)-3-[4-(dimethylamino)phenyl]acrylamide and dimethylammonium 6-cyano-1,3-dimethyl-2,4,5-trioxo-1,2,3,4,5,8-hexahydropyrido[2,3-<i>d</i>]pyrimidin-8-ide: a π-stacked dimer and a hydrogen-bonded ribbon containing three types of ring
  作者：Jairo Quiroga、Jaime Gálvez、Michael B. Hursthouse、Justo Cobo、Christopher Glidewell

  DOI：10.1107/s0108270109053785

  日期：2010.1.15

  The bond distances in 2-cyano-N-(2,6-dimethoxypyrimidin-4-yl)-3-[4-(dimethylamino)phenyl]acrylamide, C18H19N5O3, (I), and in the anionic component of the salt dimethylammonium 6-cyano-1,3-dimethyl-2,4,5-trioxo-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidin-8-ide, C2H8N2+center dot C10H7N4O3-, (II), provide evidence for the occurrence of electronic polarization. There are no hydrogen bonds in the structure of (I), instead pairs of molecules are linked into centrosymmetric dimers by a single pi-pi stacking interaction. In (II), a combination of a two-centre N-H center dot center dot center dot O hydrogen bond, a three-centre N-H center dot center dot center dot(O)(2) hydrogen bond, together utilizing all three O atoms, and a two-centre C-H center dot center dot center dot N hydrogen bond, link the components into a ribbon containing R-1(2)(6), R-2(2)(10) and R-6(6)(30) rings.
• C- and N-cyanoacetylation of 6-aminopyrimidines with cyanoacetic acid and acetic anhydride
  作者：Jairo Quiroga、Jorge Trilleras、Jaime Gálvez、Braulio Insuasty、Rodrigo Abonía、Manuel Nogueras、Justo Cobo、Antonio Marchal

  DOI：10.1016/j.tetlet.2008.07.084

  日期：2008.9

  A series of 6-aminopyrimidines are cyanoacetylated with a mixture of cyanoacetic acid and acetic anhydride. When pyrimidin-4(3H)-ones are used as substrates, the substitution occurs at C-5, however, when the substrates are substituted pyrimidines at the C-2 and C-4, the cyanoacetylation takes place at the exocyclic amino group.

  用氰基乙酸和乙酸酐的混合物将一系列6-氨基嘧啶氰基乙酰化。当使用嘧啶-4（3 H）-1作为底物时，取代发生在C-5，但是，当底物在C-2和C-4处被取代的嘧啶时，氰基乙酰化发生在环外氨基上。
• 5-Cyanoacetylpyrimidines as intermediates for 7-aryl-6-cyanopyrido[2,3-d]pyrimidin-5-ones
  作者：Jairo Quiroga、Jorge Trilleras、Jaime Gálvez、Braulio Insuasty、Rodrigo Abonía、Manuel Nogueras、Justo Cobo

  DOI：10.1016/j.tetlet.2009.08.070

  日期：2009.11

  The reactions of N-4- and 5-cyanoacetyl derivates of 4-aminopyrimidines with aromatic aldehydes have yielded the N-(pyrimidin-4-yl)-3-arylacrylamides and the dihydropyrido[2,3-d]pyrimidines, respectively. The first reaction was a Claisen-Schmidt reaction catalysed by base, and the second one proceeded via thermal cyclocondensation. (C) 2009 Elsevier Ltd. All rights reserved.