4-异丙基-6-甲基-2-氧代-1,2,3,4-四氢-5-嘧啶羧酸乙酯 | 198826-86-7

• 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: 4-异丙基-6-甲基-2-氧代-1,2,3,4-四氢-5-嘧啶羧酸乙酯
• 英文名称: 5-(ethoxycarbonyl)-4-isopropyl-6-methyl-3,4-dihydropyrimidin-2(1H)-one
• 英文别名: ethyl 4-isopropyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；5-ethoxycarbonyl-6-methyl-4-isopropyl-3,4-dihydropyrimidin-2(1H)-one；ethyl 6-methyl-2-oxo-4-propan-2-yl-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 198826-86-7
• 化学式: C₁₁H₁₈N₂O₃
• 分子量: 226.276
• InChiKey: DDXOEBXUIKNMHW-UHFFFAOYSA-N

物化性质

• 熔点：
  198-200°

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  4-异丙基-6-甲基-2-氧代-1,2,3,4-四氢-5-嘧啶羧酸乙酯 在 potassium peroxomonosulphate 、 cobalt(II) nitrate 作用下， 以 水 、 乙腈 为溶剂， 以73%的产率得到5-尿嘧啶甲酸乙酯
  参考文献：
  名称：

  An unusual oxidation–dealkylation of 3,4-dihydropyrimidin-2(1H)-ones mediated by Co(NO3)2·6H2O/K2S2O8 in aqueous acetonitrile

  摘要：

  4-Aryl-6-methyl-3,4-dihydropyrimidin-2(1H)-one (DHPM) scaffolds of Biginelli type were oxidized using Co(II)/S2O82- and the reaction afforded 6-unsubstituted pyrimidin-2(1H)-ones through an unprecedented dealkylation process. 4-Alkyl DHPMs under similar conditions afforded yet another unusual product, ethyl tetrahydropyrimidin-2,4(1H,3H)-dione-5-carboxylate. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.010
• 作为产物：
  描述：

  2-甲氧基-6-甲基-4-(1-甲基乙基)-1,4-二氢嘧啶-5-羧酸乙酯 在 盐酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 以70%的产率得到4-异丙基-6-甲基-2-氧代-1,2,3,4-四氢-5-嘧啶羧酸乙酯
  参考文献：
  名称：

  Synthesis and Aromatization of Dihydropyrimidines Structurally Related to Calcium Channel Modulators of the Nifedipine-Type

  摘要：

  DOI：

  10.3987/com-97-7931

文献信息

• A New Biginelli Reaction Procedure Using Potassium Hydrogen Sulfate as the Promoter for an Efficient Synthesis of 3,4-Dihydropyrimidin-2(1<i>H</i>)-one
  作者：Shujiang Tu、Fang Fang、Songlei Zhu、Tuanjie Li、Xiaojing Zhang、Qiya Zhuang

  DOI：10.1055/s-2004-815419

  日期：——

  conditions have been found to carry out the Biginelli reaction for the synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives. This synthesis was performed using potassium hydrogen sulfate as the promoter in glycol solution. Compared with the classical Biginelli reaction conditions, this new method has the advantage of excellent yields (85-99%) and short reaction time (0.5-2 h).

  已经发现简单和改进的条件可以进行 Biginelli 反应以合成 3,4-二氢嘧啶-2(1H)-one 衍生物。该合成是在乙二醇溶液中使用硫酸氢钾作为促进剂进行的。与经典的 Biginelli 反应条件相比，这种新方法具有收率高（85-99%）和反应时间短（0.5-2 h）的优点。
• A novel combination of (diacetoxyiodo)benzene and tert-butylhydroperoxide for the facile oxidative dehydrogenation of 3,4-dihydropyrimidin-2(1H)-ones
  作者：Nandkishor N. Karade、Sumit V. Gampawar、Jeevan M. Kondre、Girdharilal B. Tiwari

  DOI：10.1016/j.tetlet.2008.09.045

  日期：2008.11

  A clean and efficient oxidative dehydrogenation of 3,4-dihydropyrimidin-2(1H)-ones to 1,2-dihydropyrimidines has been achieved through a novel combination of (diacetoxyiodo)benzene and tert-butylhydroperoxide in CH2Cl2.

  通过在CH 2 Cl 2中将（diacetoxyiodo ）苯和叔丁基氢过氧化物进行新颖的结合，已实现了3,4-dihydropyrimidin-2（1 H）-ones的干净高效氧化脱氢成1,2-dihydropyrimidines 。
• Efficient and Green Microwave-Assisted Multicomponent Biginelli Reaction for the Synthesis of Dihydropyrimidinones Catalyzed by Heteropolyanion-Based Ionic Liquids Under Solvent-Free Conditions
  作者：Renzhong Fu、Yang Yang、Wenchen Lai、Yongfeng Ma、Zhikai Chen、Jian Zhou、Wen Chai、Quan Wang、Rongxin Yuan

  DOI：10.1080/00397911.2014.976346

  日期：2015.2.16

  Abstract An efficient and green route for the synthesis of dihydropyrimidinones via microwave-assisted Biginelli reaction catalyzed by 3 mol% of heteropolyanion-based ionic liquids under solvent-free conditions has been reported. The practical reaction was found to be compatible with different structurally diverse substrates. Good to excellent yields, short reaction times, and operational simplicity

  摘要 报道了一种在无溶剂条件下，由 3 mol% 杂多阴离子基离子液体催化的微波辅助 Biginelli 反应合成二氢嘧啶酮的高效绿色路线。发现实际反应与不同结构不同的底物相容。从良好到出色的产量、较短的反应时间和操作简单性是该协议的主要亮点。此外，基于杂多阴离子的离子液体很容易在 Biginelli 反应中重复使用。图形概要
• New environmentally friendly solvent free synthesis of dihydropyrimidinones catalysed by N-butyl-N,N-dimethyl-α-phenylethylammonium bromide
  作者：K. Rosi Reddy、Ch. Venkateshwar Reddy、M. Mahesh、P.V.K. Raju、V.V. Narayana Reddy

  DOI：10.1016/j.tetlet.2003.09.030

  日期：2003.10

  N-Butyl-N,N-dimethyl-α-phenylethylammonium bromide catalyzes efficiently the three component condensation reaction of an aromatic aldehyde, a β-keto ester and urea/thiourea under solvent free conditions at 100°C to afford the corresponding dihydropyrimidinone in high yield.

  N-丁基-N，N-二甲基-α-苯基乙基溴化铵可在无溶剂条件下于100°C下有效催化芳族醛，β-酮酸酯和脲/硫脲的三组分缩合反应，从而得到相应的二氢嘧啶酮屈服。
• Effect of high pressure on Biginelli reactions. Steric hindrance and mechanistic considerations
  作者：Gérard Jenner

  DOI：10.1016/j.tetlet.2004.05.106

  日期：2004.8

  The effect of high pressure is examined in 3-CC Biginelli reactions. This effect is small when moderately hindered aldehydes or ureas are involved. However, particularly in the case of bulky aldehydes, the sensitivity of the reaction to pressure increases with increasing steric congestion in line with earlier studies described in the reference list. The results also provide insights into the mechanism

  在3-CC Biginelli反应中检查了高压的影响。当涉及中度受阻的醛或脲时，这种作用很小。但是，特别是在大体积醛的情况下，反应对压力的敏感性会随着空间拥堵的增加而增加，这与参考文献中所述的早期研究相一致。结果还提供了对该机制的见解。这样的结果突显了高压活化在制备受阻Biginelli产品中的合成效用。