5-dimethylaminomethylidene-2,4,6(1H,3H,5H)-pyrimidinetrione | 89227-65-6

• 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-dimethylaminomethylidene-2,4,6(1H,3H,5H)-pyrimidinetrione
• 英文别名: 5-((Dimethylamino)methylene)-2,4,6(1H,3H,5H)-pyrimidinetrione；5-(dimethylaminomethylidene)-1,3-diazinane-2,4,6-trione
• CAS: 89227-65-6
• 化学式: C₇H₉N₃O₃
• mdl: MFCD00480286
• 分子量: 183.167
• InChiKey: IFJJJQASQZGSAC-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C(Solv: water (7732-18-5))
• 密度：
  1.420±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  78.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-dimethylaminomethylidene-2,4,6(1H,3H,5H)-pyrimidinetrione 在 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 5-oxo-3-[[(2,4,6-trioxohexahydropyrimidin-5-ylidene)methyl]amino]-5,6,7,8-tetrahydro-2H-1-benzopyran-2-one
  参考文献：
  名称：

  N，N-二甲基烯胺中的二甲胺取代。皂苷类似物和3-氨基四氢香豆素衍生物的合成

  摘要：

  从5-二甲基氨基亚甲基-2,4,6（1 H，3 H，5 H）-嘧啶三酮和吲哚衍生物制备了一些新的六元皂苷类似物。还合成了2-[[（（2,4,6-三氧六氢嘧啶-5-亚甲基）甲基]氨基] -3-二甲基氨基丙酸酯，并将其用于稠合的2 H-吡喃-2-酮的合成中。

  DOI：

  10.1016/s0040-4020(01)00174-0
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 6-hydroxyuracil 在 三氯氧磷 作用下， 反应 3.0h， 以88%的产率得到5-dimethylaminomethylidene-2,4,6(1H,3H,5H)-pyrimidinetrione
  参考文献：
  名称：

  A New and Facile Synthesis of Pyrido[2,3-d: 6,5-d′]dipyrimidine Derivatives

  摘要：

  DOI：

  10.1055/s-1983-30571

文献信息

• Synthesis of 3-Pyrazolyl-1,2,4-Triazoles via One-Pot Multicomponent Reaction in Phosphoric Acid
  作者：Amer Amer、Amr Moustafa

  DOI：10.1055/s-0035-1561945

  日期：——

  A high-yielding synthetic route towards pyrazolyl-[1,2,4]triazole derivatives has been developed via one-pot multicomponent reaction of polyfunctionalized triazoles, DMF–DMA, acetophenone, ethyl cyanoacetate, and/or 3-oxo-3-phenylpropanenitrile in ortho-phosphoric acid (85%). In the same manner, a new series of 2-triazolyl-tetrahydro-indazol-4-ones and pyrazolo[3,4-d]pyrimidines has been synthesized

  通过多官能化三唑、DMF-DMA、苯乙酮、氰基乙酸乙酯和/或3-氧代-3-苯丙腈的一锅多组分反应，开发了一种高产率的吡唑基-[1,2,4]三唑衍生物合成路线在正磷酸 (85%) 中。以同样的方式，通过三唑、DMF-DMA 和 1,3-环己二酮和/或 2-三唑基-四氢-吲唑-4-酮和吡唑并[3,4-d]嘧啶的反应合成了一系列新的 2-三唑基-四氢-吲唑-4-酮和/或吡唑并[3,4-d]嘧啶。分别为巴比妥酸。通过三唑与相应烯胺酮在正磷酸 (85%) 中的反应，以经典方式制备相同的产物。
• Synthesis, structure, and solvatochromism of merocyanine dyes based on barbituric acid
  作者：A. V. Kulinich、N. A. Derevyanko、A. A. Ishchenko

  DOI：10.1134/s1070363206090167

  日期：2006.9

  Di-, tetra-, and hexamethinemerocyanines were synthesized on the basis of barbituric and 1,3-dimethylbarbituric acids and heterocycles characterized by a strong (1-benzyl-1,2-dihydrobenzo[cd]indole), medium (1,3-dihydro-1,3,3-trimethyl-2H-indole and 3-ethyl-2,3-dihydro-1,3-benzothiazole), and strong electron-donor power (1,3-diphenyl-2,3-dihydro-1H-benzirnidazole). Their solvatochromic properties were analyzed using both conventional parameters (absorption maxima and molar absorption coefficients) and centroids, oscillator strengths, widths, asymmetry and excess coefficients, and fine structure of the long-wave absorption bands, which were determined by mathematical processing (method of moments). A combination of these parameters unambiguously characterizes limiting electronic states of merocyanines (neutral polyene, polymethine, or charged polyene) responsible for the type of solvatochronism. Relations were found between solvatochromic properties, on the one hand, and donor-acceptor power of the terminal groups, length of the polymethine chain, and solvent nature, on the other. The difference in solvatochromism (up to reversal of sign) of merocyanines derived from barbituric acid and their analogs based on 1,3-dimethylbarbituric acid originates from both the difference in their electronic asymmetry and the ability of the NH groups in the former to participate in hydrogen bonding with proton-acceptor solvents.
• Selic, Lovro; Recnik, Simon; Stanovnik, Branko, Heterocycles, 2002, vol. 58, p. 577 - 585
  作者：Selic, Lovro、Recnik, Simon、Stanovnik, Branko

  DOI：——

  日期：——
• Yousif, Mohammed M.; Saeki, Seitaro; Hamana, Masatomo, Heterocycles, 1981, vol. 15, # 2, p. 1083 - 1088
  作者：Yousif, Mohammed M.、Saeki, Seitaro、Hamana, Masatomo

  DOI：——

  日期：——
• YOUSIF M. M.; SAEKI SEITARO; HAMMA MASATOMU, HETEROCYCLES, 1981, 15, NO 2, SPEC ISSUE, 1083-1088
  作者：YOUSIF M. M.、 SAEKI SEITARO、 HAMMA MASATOMU

  DOI：——

  日期：——