5-(2,4,6-trimethylbenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione | 1393602-66-8

• 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-(2,4,6-trimethylbenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
• CAS: 1393602-66-8
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: MZQYQKMONKQQAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  75.27
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-(2,4,6-trimethylbenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以59%的产率得到2,4,6-trimethylbenzaldehyde-¹⁸O
  参考文献：
  名称：

  A Cost-Effective Way to Produce Gram-Scale ¹⁸O-Labeled Aromatic Aldehydes

  摘要：

  DOI：

  10.1021/acs.orglett.2c01637
• 作为产物：
  描述：

  巴比妥酸 、 C-mesityl-N-methylnitrone 以 二氯甲烷 为溶剂， 反应 12.0h， 以76%的产率得到5-(2,4,6-trimethylbenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
  参考文献：
  名称：

  Solvent-dependent reactivities of acyclic nitrones with β-diketones: catalyst-free syntheses of endiones and enones

  摘要：

  Reactions of the nitrones -O+N(Me)=C(H)Ar 1 (Ar=phenyl 1a, 4-methylphenyl 1b, 2,4,6-trimethylphenyl 1c, and anthracen-9-yl 1d) with the cyclic beta-diketones 1,3-indandione 2 or barbituric acid 3 in CH2Cl2, afford the corresponding endiones 2'a-2'd or 3'a-3'd. In contrast, dimedone 4 reacts with 1a or 1b to give the endione 4'a or 4'b and the bis-adduct 4 '' a or 4 '' h. Nevertheless, reaction of 4 with 1c or 1d in CH2Cl2 furnishes only the endione adducts 4'c or 4'd. However, the reaction of 4 with 1a or 1b in methanol gives only 4 '' a or 4 '' b, respectively. Among acyclic beta-diketones only malonic acid 7 reacts with 1a-1c. Reaction of 7 with 1a in CH2Cl2 forms cinnamic acid 7 '' a, whereas in the case of 1b, the endione 7'b and (E)-3-p-tolylacrylic acid 7 '' b are obtained. The nitrone 1c reacts with 7 in CH2Cl2 to afford the endione 7'c or with acetone yielding (E)-4-mesitylbut-3-en-2-one 8. X-ray analyses are reported for 4'c, 5, and 7 '' b. In addition, the calculated acidity of the hydrogen at the alpha-C atom is shown to correlate with the reactivity of the beta-diketones with nitrones. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.086