5-(propan-2-ylidene)pyrimidine-2,4,6(1H,3H,5H)-trione | 446878-62-2

• 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-(propan-2-ylidene)pyrimidine-2,4,6(1H,3H,5H)-trione
• 英文别名: 5-Propan-2-ylidene-1,3-diazinane-2,4,6-trione
• CAS: 446878-62-2
• 化学式: C₇H₈N₂O₃
• 分子量: 168.152
• InChiKey: CXXWNPXLWUFMAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  75.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  巴比妥酸 、 丙酮 反应 12.0h， 以87%的产率得到5-(propan-2-ylidene)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

文献信息

• Medicinal drug with activity against gram positive bacteria, mycobacteria and fungi
  申请人：Levina Elizabeth

  公开号：US10265318B2

  公开（公告）日：2019-04-23

  A medicinal drug is provided with activity against gram positive bacteria, mycobacteria and fungi characterized in that it is a compound of the class of pyrimidine derivatives of salicylic aldehyde and perhydropyrimidine-2,4,6-triones selected from a group consisting of tautomeric forms, salt forms, and a cyclic form of pyrylium salts, and with the general formula: where X1, X3 are selected from the group containing: H, halogen; NO2; X2, X4 are selected from the group containing: H, halogen; Z is selected from the group containing: O, NNH2, NOH, perhydropyrimidine-5-ylidene-2,4.6-trione, perhydropyrimidine-5-ylidene-2,4.6-trione, substituted at the nitrogen atom with alkyl, aryl or aralkyl group; Y is selected from the group containing: H, Na, Li, K. Further, methods for treating infections, tonsillitis, pneumonia, or wound infections caused by Gram-positive bacteria, mycobacteria and fungi are provided using a therapeutically effective amount of the compound.

  提供了一种对革兰氏阳性菌、分枝杆菌和真菌具有活性的药物，其特征在于它是一种水杨醛和过氢嘧啶-2,4,6-三酮的嘧啶衍生物类化合物，该化合物从同分异构体、盐类和环状嘧啶盐组成的组中选出，通式为 其中 X1、X3 选自以下组别H、卤素 X2、X4 选自包含以下物质的组H、卤素； Z 选自包含以下物质的组O、NNH2、NOH、全氢嘧啶-5-亚基-2,4.6-三酮、全氢嘧啶-5-亚基-2,4.6-三酮，在氮原子上被烷基、芳基或芳烷基取代； Y 选自以下组别H、Na、Li、K。 此外，还提供了使用治疗有效量的化合物治疗革兰氏阳性菌、分枝杆菌和真菌引起的感染、扁桃体炎、肺炎或伤口感染的方法。
• ULTRAVIOLET ABSORBENT COMPOSITION
  申请人：Furukawa Kazushi

  公开号：US20110155976A1

  公开（公告）日：2011-06-30

  An ultraviolet absorbent composition, having ultraviolet absorbent A and a silicon compound, in which the ultraviolet absorbent A has a maximum absorption wavelength from 350 nm to 400 nm, a half value width of 55 nm or less, and the molar extinction coefficient of 20000 or more at the maximum absorption wavelength.
• Medicinal Drug with Activity against Gram Positive Bacteria, Mycobacteria and Fungi
  申请人：Levina Elizabeth

  公开号：US20170035758A1

  公开（公告）日：2017-02-09

  A medicinal drug is provided with activity against gram positive bacteria, mycobacteria and fungi characterized in that it is a compound of the class of pyrimidine derivatives of salicylic aldehyde and perhydropyrimidine-2,4,6-triones selected from a group consisting of tautomeric forms, salt forms, and a cyclic form of pyrylium salts, and with the general formula: where X1, X3 are selected from the group containing: H, halogen; NO 2 ; X2, X4 are selected from the group containing: H, halogen; Z is selected from the group containing: O, NNH 2 , NOH, perhydropyrimidine-5-ylidene-2,4.6-trione, perhydropyrimidine-5-ylidene-2,4.6-trione, substituted at the nitrogen atom with alkyl, aryl or aralkyl group; Y is selected from the group containing: H, Na, Li, K. Further, methods for treating infections, tonsillitis, pneumonia, or wound infections caused by Gram-positive bacteria, mycobacteria and fungi are provided using a therapeutically effective amount of the compound.
• Solvent-dependent reactivities of acyclic nitrones with β-diketones: catalyst-free syntheses of endiones and enones
  作者：Jamal Lasri、Grzegorz Gajewski、M. Fátima C. Guedes da Silva、Maxim L. Kuznetsov、Ricardo R. Fernandes、Armando J.L. Pombeiro

  DOI：10.1016/j.tet.2012.06.086

  日期：2012.9

  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.