6-methyl-1,3-oxazine-2,4(3H)-dione | 2911-21-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 6-methyl-1,3-oxazine-2,4(3H)-dione
• 英文别名: 2H-1,3-Oxazine-2,4(3H)-dione, 6-methyl-；6-methyl-1,3-oxazine-2,4-dione
• CAS: 2911-21-9
• 化学式: C₅H₅NO₃
• 分子量: 127.1
• InChiKey: AQJVRSQXEZBCAO-UHFFFAOYSA-N

物化性质

• 熔点：
  231-232 °C
• 密度：
  1.299±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methyl-1,3-oxazine-2,4(3H)-dione 在 溶剂黄146 作用下， 反应 4.0h， 生成 6-甲基-1-苯基嘧啶-2,4(1h,3h)-二酮
  参考文献：
  名称：

  Heterocyclic transformations. Part 5: Studies in reactions of 6-methyl -l,3-oxazine-2,4(3H)-dione with arylamines—a facile synthesis of 1-aryl-6-methyluracils

  摘要：

  6-Methyl-1,3-oxazine-2,4(3H)-dione 1 reacts with 2 equiv. arylamines 3 at 150-160-degrees-C to give 1-aryl-6-methyluracils 5 or 1-aryl-3- (3-aryliminobutanoyl) ureas 4. The latter-as well as mixtures of 1 and 3 (2 equiv.) on refluxing, in isopentanol in some cases or in acetic acid in general-provide a facile synthesis of 5. The role of the stoichiometric excess of arylamines as against an equiv. of an alkylamine in similar reactions has been rationalized.

  DOI：

  10.1039/p19930000731
• 作为产物：
  描述：

  5-Acetyl-4-hydroxy-2H-1,3-thiazine-2,6(3H)-dione 在 吡啶 作用下， 以73%的产率得到6-methyl-1,3-oxazine-2,4(3H)-dione
  参考文献：
  名称：

  Azines and azoles: CXXV. New regioselective synthesis of 1-amino-6-methyluracils

  摘要：

  Readily accessible 5-acetyl-4-hydroxy-3,6-dihydro-2H-1,3-thiazine-2,6-dione reacts with substituted hydrazines and carboxylic acid hydrazides under mild conditions to give the corresponding hydrazones. Under severe conditions (heating in boiling dimethylformamide) the reaction is accompanied by extrusion of COS with formation of substituted 1-amino-6-methyluracils. Reactions of 5-acetyl-4-hydroxy-3,6dihydro-2H-1,3-thiazine-2,6-dione with monosubstituted alkyl- and arylhydrazines take different pathways, depending on the conditions. Heating of equimolar mixtures of the reactants in ethanol or propan-1-of leads to the formation of 2-substituted 5-methyl-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxamides rather than 1-amino-6-methyluracil derivatives.

  DOI：

  10.1134/s1070363207120134

文献信息

• A Convenient Approach to meso-Uracil–4,4-Difluoro-4-bora-3a, 4a-diaza-s-indacene Derivatives
  作者：M. Cordaro、M. Trapani、M. A. Castriciano、J. A. A. W. Elemans、A. Nicosia、P. Mineo

  DOI：10.1055/a-1545-7086

  日期：2021.10

  4a-diaza-s-indacene (BODIPY). In this way, regioselectively functionalized BODIPYs with a direct connection to a nucleobase were prepared in yields of 30–45%. MALDI-TOF mass spectrometry, NMR, UV/vis absorption, and steady-state and time-­resolved fluorescence spectroscopies were used to characterize the structures and the spectroscopic/photophysical properties of the resultant dyes.

  已开发出一种有效且方便的合成 1-取代尿嘧啶-6-甲醛衍生物的方案。三步序列允许使用低成本前体大量制备在 N-1 处具有各种取代基的尿嘧啶-6-甲醛。醛官能化尿嘧啶用作制备 4,4-二氟-4-bora-3a,4a-二氮杂-s-茚(BODIPY) 的内消旋-(1-取代的6-尿嘧啶)-衍生物的有用前体。通过这种方式，以 30-45% 的产率制备了与核碱基直接连接的区域选择性功能化 BODIPY。MALDI-TOF 质谱、核磁共振、紫外/可见吸收以及稳态和时间分辨荧光光谱用于表征所得染料的结构和光谱/光物理特性。
• Pyrimidine derivatives and related compounds. Part 42. Isolation of the intermediates in the ring transformation of 1,3-oxazine-2,4-diones into pyrimidines and pyrazoles, and their structure determination by 15N nuclear magnetic resonance analysis
  作者：Motoi Yogo、Kosaku Hirota、Shigeo Senda

  DOI：10.1039/p19820000473

  日期：——

  3-oxazine-2,4-diones (1) and (2) with hydrazine hydrate at room temperature gave the 6-hydroxy-5,6-dihydrouracils (7a) and (8a). The structures of the products were determined by 15N n.m.r. analysis. The mechanism of the ring transformation of 1,3-oxazines into pyrimidines and pyrazoles is discussed.

  6-甲基-1,3-恶嗪-2,4-二酮（1）和（2）与水合肼在室温下反应，得到6-羟基-5,6-二氢尿嘧啶（7a）和（8a）。产物的结构通过15 N nmr分析确定。讨论了1，3-恶嗪环转化为嘧啶和吡唑的机理。
• 一种含有6-甲基尿嘧啶结构化合物的制备方法
  申请人：诚达药业股份有限公司

  公开号：CN111333586A

  公开（公告）日：2020-06-26

  本发明公开了一种含有6～甲基尿嘧啶结构化合物的制备方法，涉及医药中间体和有机化工中间体合成技术领域，包括下述合成步骤：(1)化合物1氨基甲酸乙酯与和化合物2乙酰乙酸乙酯在加热条件以及有机溶剂和催化剂的作用下反应生成化合物3噁嗪二酮，(2)将化合物3与化合物4 2‑氟‑6‑(三氟甲基)苯基)甲胺在加热、有机溶剂或无溶剂的条件下反应生成化合物5，即6～甲基～尿嘧啶取代衍生物，本发明的合成方法适用于工业化生产、成本较低、制得的产品纯度高、收率高。
• Kumar, Subodh; Saini, Rummi; Singh, Harjit, Journal of the Chemical Society. Perkin transactions I, 1992, # 15, p. 2011 - 2016
  作者：Kumar, Subodh、Saini, Rummi、Singh, Harjit

  DOI：——

  日期：——
• Singh, Harjit; Aggarwal, Pawan; Kumar, Subodh, Journal of the Chemical Society. Perkin transactions I, 1992, # 9, p. 1139 - 1144
  作者：Singh, Harjit、Aggarwal, Pawan、Kumar, Subodh

  DOI：——

  日期：——