3-methyl-1-(p-nitrophenyl)uracil | 128039-16-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-methyl-1-(p-nitrophenyl)uracil
• 英文别名: 3-methyl-1-(4-nitrophenyl)uracil；3-Methyl-1-(4-nitrophenyl)pyrimidine-2,4-dione
• CAS: 128039-16-7
• 化学式: C₁₁H₉N₃O₄
• 分子量: 247.21
• InChiKey: JMUIGDDANPOGBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  86.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methyl-1-(p-nitrophenyl)uracil 在 硫酸 、 硝酸 作用下， 生成 3-methyl-1-(4-nitrophenyl)-5-nitrouracil
  参考文献：
  名称：

  尿嘧啶衍生物N-1芳构化的简便方法

  摘要：

  1-（4-硝基苯基）-和1-（2,4-二硝基苯基）尿嘧啶衍生物是通过使用1-氟-4-硝基苯或1-氟-2,4将尿嘧啶及其5-取代衍生物直接芳基化制得的-二硝基苯在碱的存在下。还介绍了新获得的尿嘧啶衍生物在进一步合成中的应用。

  DOI：

  10.1016/j.tetlet.2006.04.130
• 作为产物：
  描述：

  5-cyano-3-methyl-1-(4-nitrophenyl)uracil 在 氢溴酸 作用下， 反应 4.0h， 以87%的产率得到3-methyl-1-(p-nitrophenyl)uracil
  参考文献：
  名称：

  在5位上具有吸电子基团的尿嘧啶衍生物与胺的新反应：尿嘧啶N 1部分与胺之间的交换反应

  摘要：

  具有在5-位的吸电子基团例如硝基，氨基甲酰基和氰基的1，3-二取代的尿嘧啶与伯胺的反应导致尿嘧啶环的N 1部分与胺部分交换。交换反应受5-和N 1-位上取代基的性质影响。用加成，开环和闭环的方式解释反应顺序。

  DOI：

  10.1039/p19900000367

文献信息

• N-Functionalization of uracil derivatives: synthesis of chiral 2-(3-methyl-5-nitro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)alkanoic acids and their methyl esters
  作者：Andrzej Gondela、Krzysztof Walczak

  DOI：10.1016/j.tetasy.2005.05.009

  日期：2005.6

  3-Methyl-5-nitro-1-(4-nitrophenyl)uracil has been obtained by regioselective arylation of uracil using 4-nitrofluorobenzene, followed by methylation at the nitrogen atom N-3 and subsequent nitration of the uracil ring. 3-Methyl-5-nitro-1-(4-nitrophenyl)uracil, which was treated with either certain amino acids methyl ester or free amino acids underwent an ANRORC type substitution reaction. Appropriate methyl 2-substituted alkanoates or alkanoic acids containing 3-methyl-5-nitrouracil parts were obtained in satisfactory yields. A similar reaction can be carried out using 5-cyano-3-methyl-1-(4-nitrophenyl)uracil as a substrate. (c) 2005 Elsevier Ltd. All rights reserved.
• HIROTA, KOSAKU;KITADE, YUKIO;SAJIKI, HIRONAO;MAKI, YOSHIFUMI;YOGO, MOTOI, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 367-373
  作者：HIROTA, KOSAKU、KITADE, YUKIO、SAJIKI, HIRONAO、MAKI, YOSHIFUMI、YOGO, MOTOI

  DOI：——

  日期：——
• Novel reaction of uracil derivatives possessing electron-withdrawing groups at the 5-position with amines: exchange reaction between the N1-portion of uracils and amines
  作者：Kosaku Hirota、Yukio Kitade、Hironao Sajiki、Yoshifumi Maki、Motoi Yogo

  DOI：10.1039/p19900000367

  日期：——

  The reaction of 1,3-disubstituted uracils possessing an electron-withdrawing group such as nitro, carbamoyl, and cyano at the 5-position with primary amines resulted in the exchange of the N1-portion of the uracil ring with the amine moiety. The exchange reactions were influenced by the nature of substituents at the 5- and N1-position. The reaction sequence is explained in terms of addition, ring-opening

  具有在5-位的吸电子基团例如硝基，氨基甲酰基和氰基的1，3-二取代的尿嘧啶与伯胺的反应导致尿嘧啶环的N 1部分与胺部分交换。交换反应受5-和N 1-位上取代基的性质影响。用加成，开环和闭环的方式解释反应顺序。
• A convenient method for N-1 arylation of uracil derivatives
  作者：Andrzej Gondela、Krzysztof Walczak

  DOI：10.1016/j.tetlet.2006.04.130

  日期：2006.7

  1-(4-Nitrophenyl)- and 1-(2,4-dinitrophenyl)uracil derivatives have been obtained by direct arylation of uracil and its 5-substituted derivatives using 1-fluoro-4-nitrobenzene or 1-fluoro-2,4-dinitrobenzene in the presence of a base. The application of the newly obtained uracil derivatives in further synthesis is also presented.

  1-（4-硝基苯基）-和1-（2,4-二硝基苯基）尿嘧啶衍生物是通过使用1-氟-4-硝基苯或1-氟-2,4将尿嘧啶及其5-取代衍生物直接芳基化制得的-二硝基苯在碱的存在下。还介绍了新获得的尿嘧啶衍生物在进一步合成中的应用。