5-硝基-4,6-二苯基-3,4-二氢-2(1H)-嘧啶酮 | 37673-85-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-硝基-4,6-二苯基-3,4-二氢-2(1H)-嘧啶酮
• 英文名称: 5-nitro-4,6-diphenyl-3,4-dihydro-(1H)-pyrimidin-2-one
• 英文别名: 5-nitro-4,6-diphenyl-3,4-dihydropyrimidin-2(1H)-one；5-nitro-4,6-diphenyl-3,4-dihydro-1H-pyrimidin-2-one；5-Nitro-2-oxo-4.6-diphenyl-1.2.3.4-tetrahydro-pyrimidin；5-Nitro-4,6-diphenyl-3,4-dihydro-2(1H)-pyrimidinone；5-nitro-4,6-diphenyl-3,4-dihydro-1H-pyrimidin-2-one
• CAS: 37673-85-1
• 化学式: C₁₆H₁₃N₃O₃
• 分子量: 295.298
• InChiKey: MNSGYEZSEDWFPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  87
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  5-硝基-4,6-二苯基-3,4-二氢-2(1H)-嘧啶酮 在 溴 作用下， 以 氯仿 为溶剂， 反应 245.08h， 生成 5-Nitro-2-hydroxy-4.6-diphenyl-pyrimidin
  参考文献：
  名称：

  Bromination-Dehydrobromination of 4-Aryl-5-nitro-6-phenyl-3,4-dihydropyrimidin-2(1H)-ones

  摘要：

  根据不同的条件，4-芳基-5-硝基-6-苯基-3,4-二氢嘧啶-2(1H)-酮溴化和随后的脱氢溴化可以得到 4-芳基-5-硝基-6-苯基嘧啶-2(1H)-酮或它们与相应的 4-芳基-5-溴-6-甲氧基-5-硝基-6-苯基四氢嘧啶-2-酮的混合物，后者形成两种非对映异构体。

  DOI：

  10.1007/s11178-005-0180-4
• 作为产物：
  描述：

  苯甲醛 、 尿素 、 苯甲酰硝基甲烷 在 三氯化铁 盐酸 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以27%的产率得到5-硝基-4,6-二苯基-3,4-二氢-2(1H)-嘧啶酮
  参考文献：
  名称：

  Synthesis of 5-nitro-3,4-dihydropyrimidin-2(1H)-ones catalyzed by metal salts. Retro-Henry reaction with formation of N,N′-disubstituted ureas

  摘要：

  Three-component condensation of alpha-nitroacetophenone with aromatic aldehydes and urea in the presence of iron(III), cobalt(II), nickel(II), and copper(II) salts as catalyst led to the formation of 4,6-diaryl-5-nitro-3,4-dihydropyrimidin-2(1H)-ones and N-benzoyl-N'-(1-aryl-2-nitroethyl)ureas. The latter were formed as a result of retro-nitroaldol (retro-Henry) reaction of intermediate 4,6-diaryl-6-hydroxy-5-nitro-3,4,5,6-tetra-hydropyrimidin-2(1H)-ones.

  DOI：

  10.1134/s1070428007010113

文献信息

• Selective acylation of 5-nitro- and 5-ethoxycarbonyl-4,6-diaryl-3,4-dihydropyrimidin-2(1H)-ones
  作者：V. F. Sedova、O. P. Shkurko

  DOI：10.1134/s1070428010110163

  日期：2010.11

  The acetylation and chloroacetylation of 5-nitro- and 5-ethoxycarbonyl-substituted 4,6-diaryl-3,4-dihydropyrimidin-2(1H)-ones proceeds regioselectively at the N3 atom of the heterocycle whereas the acetylation of the 5-aryloxy-substituted analog results in a mixture of N1- and N3-acetylated regioisomers.

  5-硝基和5-乙氧基羰基取代的4,6-二芳基-3,4-二氢嘧啶-2（1 H）-ones的乙酰化和氯乙酰化在杂环的N 3原子上区域选择性地进行，而5的乙酰化-芳氧基取代的类似物产生N 1-和N 3-乙酰化的区域异构体的混合物。
• Synthesis of 5-nitro-3,4-dihydropyrimidin-2(1H)-ones catalyzed by metal salts. Retro-Henry reaction with formation of N,N′-disubstituted ureas
  作者：V. F. Sedova、V. P. Krivopalov、O. P. Shkurko

  DOI：10.1134/s1070428007010113

  日期：2007.1

  Three-component condensation of alpha-nitroacetophenone with aromatic aldehydes and urea in the presence of iron(III), cobalt(II), nickel(II), and copper(II) salts as catalyst led to the formation of 4,6-diaryl-5-nitro-3,4-dihydropyrimidin-2(1H)-ones and N-benzoyl-N'-(1-aryl-2-nitroethyl)ureas. The latter were formed as a result of retro-nitroaldol (retro-Henry) reaction of intermediate 4,6-diaryl-6-hydroxy-5-nitro-3,4,5,6-tetra-hydropyrimidin-2(1H)-ones.
• Bromination-Dehydrobromination of 4-Aryl-5-nitro-6-phenyl-3,4-dihydropyrimidin-2(1H)-ones
  作者：V. F. Sedova、Yu. V. Gatilov、O. P. Shkurko

  DOI：10.1007/s11178-005-0180-4

  日期：2005.3

  Depending on the conditions, bromination of 4-aryl-5-nitro-6-phenyl-3,4-dihydropyrimidine-2(1H)-ones and subsequent dehydrobromination gives either 4-aryl-5-nitro-6-phenylpyrimidin-2(1H)-ones or their mixtures with the corresponding 4-aryl-5-bromo-6-methoxy-5-nitro-6-phenyltetrahydropyrimidin-2-ones which are formed as two diastereoisomers.

  根据不同的条件，4-芳基-5-硝基-6-苯基-3,4-二氢嘧啶-2(1H)-酮溴化和随后的脱氢溴化可以得到 4-芳基-5-硝基-6-苯基嘧啶-2(1H)-酮或它们与相应的 4-芳基-5-溴-6-甲氧基-5-硝基-6-苯基四氢嘧啶-2-酮的混合物，后者形成两种非对映异构体。