5-(3-hydroxybenzylidene)-1,3-dimethylbarbituric acid | 57270-88-9

• 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-(3-hydroxybenzylidene)-1,3-dimethylbarbituric acid
• 英文别名: 5-(3-hydroxy-benzylidene)-1,3-dimethyl-pyrimidine-2,4,6-trione；5-(3-hydroxy-benzylidene)-1,3-dimethyl-barbituric acid；5-(3-Hydroxy-benzyliden)-1,3-dimethyl-barbitursaeure；m-Hydroxybenzyliden-dimethyl-barbitursaeure；5-[(3-Hydroxyphenyl)methylidene]-1,3-dimethyl-1,3-diazinane-2,4,6-trione
• CAS: 57270-88-9
• 化学式: C₁₃H₁₂N₂O₄
• 分子量: 260.249
• InChiKey: FWVFVLXOJGZPAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  77.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-二溴甲醛肟 、 5-(3-hydroxybenzylidene)-1,3-dimethylbarbituric acid 在 potassium hydrogencarbonate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以99%的产率得到4-bromo-1-(3-hydroxyphenyl)-7,9-dimethyl-2-oxa-3,7,9-triaza-spiro[4.5]dec-3-ene-6,8,10-trione
  参考文献：
  名称：

  Synthesis of spiro 3-bromo-4,5-dihydroisoxazoles via [1,3]dipolar cycloaddition reactions

  摘要：

  A group of novel 4-bromo-7,9-dimethyl-1-aryl-2-oxa-3,7,9-triaza-spiro[4.5]dec-3-ene-6,8,10-trione derivatives is prepared through 1,3-dipolar cycloadditions between benzylidenes and bromonitrile oxide. This reaction is shown to have high atom economy. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.02.006
• 作为产物：
  描述：

  1,3-二甲基巴比妥酸 、 间羟基苯甲醛 以 水 为溶剂， 反应 2.0h， 生成 5-(3-hydroxybenzylidene)-1,3-dimethylbarbituric acid
  参考文献：
  名称：

  Discovery of cinnamamide-barbiturate hybrids as a novel class of Nrf2 activator against myocardial ischemia/reperfusion injury

  摘要：

  DOI：

  10.1016/j.bioorg.2022.105828

文献信息

• New Strategy for the Synthesis of 5-Aryl-1H,1'H-spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]2,2',4,4',6'(3H,3'H,5H)-pentaones and Their Sulfur Analogues
  作者：Mohammad Jalilzadeh、Nader Noroozi Pesyan

  DOI：10.5012/bkcs.2011.32.9.3382

  日期：2011.9.20

  Reaction of barbituric acid (BA), 1,3-dimethyl barbituric acid (DMBA) and 2-thiobarbituric acid (TBA) with cyanogen bromide and aldehydes in the presence of L-(+)-tartaric acid afforded a new route for the synthesis of stable heterocyclic 5-aryl-1H,1'H-spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]2,2',4,4',6'(3H,3'H,5H)pentaones which is a dimeric form of barbiturate (uracil and thiouracil derivative)

  在 L-(+)-酒石酸存在下，巴比妥酸 (BA)、1,3-二甲基巴比妥酸 (DMBA) 和 2-硫代巴比妥酸 (TBA) 与溴化氰和醛的反应为合成稳定的 5-芳基-1H-杂环提供了一条新途径、1'H-螺[呋喃并[2,3-d]嘧啶-6,5'-嘧啶]2,2',4,4',6'(3H,3'H,5H)-五酮，它是巴比妥酸（尿嘧啶和硫尿嘧啶衍生物）的二聚体形式。在与 1,3-二乙基硫代巴比妥酸（DETBA）的反应中，在相同条件下得到了克诺文纳格尔缩合物，然后得到了迈克尔加合物。通过 $^1H$ NMR、$^13}C$ NMR、傅立叶变换红外光谱和质量分析进行了结构阐释。讨论了其形成机理。
• Akabori, Chemische Berichte, 1933, vol. 66, p. 151,158
  作者：Akabori

  DOI：——

  日期：——
• Effect of Reaction Parameters on the Synthesis of 5-Arylidene Barbituric Acid Derivatives in Ball Mills
  作者：Robert Schmidt、Christine F. Burmeister、Matej Baláž、Arno Kwade、Achim Stolle

  DOI：10.1021/op5003787

  日期：2015.3.20

  The influence of crucial reaction parameters on Knoevenagel condensation in planetary ball mills was investigated. Rotation frequency (nu(rot)), milling ball diameter (d(MB)), milling ball filling degree (Phi(MB)), and beaker size had obvious influences on yield. It was found that higher nu(rot), lower d(MB), milling beakers with larger diameter, and a Phi(MB) of similar to 0.3 are advantageous for the reaction. Furthermore, the influence of the type of mill was investigated, including reactions performed in different planetary and mixer ball mills, in a stirred media mill, and with a mortar mill. Comparisons with the other solvent-free synthetic routes showed that ball milling is an effective way of performing the reaction with low energy intensity.
• Synthesis of spiro 3-bromo-4,5-dihydroisoxazoles via [1,3]dipolar cycloaddition reactions
  作者：Ebrahim Soleimani、Hossein Yazdani、Parisa Saei

  DOI：10.1016/j.tetlet.2015.02.006

  日期：2015.3

  A group of novel 4-bromo-7,9-dimethyl-1-aryl-2-oxa-3,7,9-triaza-spiro[4.5]dec-3-ene-6,8,10-trione derivatives is prepared through 1,3-dipolar cycloadditions between benzylidenes and bromonitrile oxide. This reaction is shown to have high atom economy. (C) 2015 Elsevier Ltd. All rights reserved.
• Discovery of cinnamamide-barbiturate hybrids as a novel class of Nrf2 activator against myocardial ischemia/reperfusion injury
  作者：Bo Wei、Ji Zhang、Nan-Nan Li、Long-Hua Yang、Xue-Li Xu、Yang-Yang Shi、Shao-Hui Liu、Ya-Jing Chen

  DOI：10.1016/j.bioorg.2022.105828

  日期：2022.7