6-methyl-2-oxo-4-propyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester | 198826-87-8

• 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: 6-methyl-2-oxo-4-propyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester
• 英文别名: 6-methyl-2-oxo-4-propyl-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester；ethyl 1,2,3,4-tetrahydro-6-methyl-2-oxo-4-propylpyrimidine-5-carboxylate；ethyl 4-propyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；ethyl 6-methyl-2-oxo-4-propyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate；5-(ethoxycarbonyl)-6-methyl-4-(n-propyl)-3,4-dihydropyrimidin-2(1H)-one；4-(n-propyl)-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(1H)-one；Ethyl 6-methyl-2-oxo-4-propyl-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate；ethyl 6-methyl-2-oxo-4-propyl-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 198826-87-8
• 化学式: C₁₁H₁₈N₂O₃
• 分子量: 226.276
• InChiKey: PEBUHSRIKMOEDR-UHFFFAOYSA-N

物化性质

• 熔点：
  153-155 °C
• 沸点：
  313.8±42.0 °C(Predicted)
• 密度：
  1.064±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  5
• 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

反应信息

• 作为反应物：
  描述：

  6-methyl-2-oxo-4-propyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester 在 氧化亚氮 作用下， 以 乙腈 为溶剂， 以94%的产率得到Ethyl 6-methyl-3-nitroso-2-oxo-4-propyl-1,4-dihydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Regioselective N-nitrosation of dihydropyrimidinones with nitric oxide

  摘要：

  N-Nitrosation of dihydropyrimidinones with nitric oxide occurred regioselectively, giving the corresponding N(3)-nitrosamides in high yields. The reaction most likely took place by a nucleophilic attack. Aprotic and polar solvents, such as CH3CN and tetrahydrofurane (THF) greatly favored the reaction, whereas protic solvents with high dielectric constant, such as CH3OH and water, disfavored it. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.12.035
• 作为产物：
  描述：

  ethyl 2-methoxy-6-methyl-4-propyl-1,4-dihydropyrimidine-5-carboxylate 在 盐酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 以65%的产率得到6-methyl-2-oxo-4-propyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester
  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

• Concentrated solar radiation as a renewable heat source for a preparative-scale and solvent-free Biginelli reaction
  作者：Yatin U. Gadkari、Navnath T. Hatvate、Balaram S. Takale、Vikas N. Telvekar

  DOI：10.1039/d0nj01351j

  日期：——

  A well-known Biginelli reaction for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones was performed in an environmentally responsible manner. Large numbers of substrates were screened, and found to give excellent yields of the desired products. In addition to the synthesis of drug molecules, the reaction was easily scaled up to 50 mmol. The present method was also energy efficient and saved

  以对环境负责的方式进行了众所周知的Biginelli反应，该反应用于合成3,4-二氢嘧啶-2（1 H）-酮/硫酮。筛选了大量的底物，发现得到所需产物的优异产率。除了合成药物分子外，该反应还容易扩大到50 mmol。与传统方法相比，本方法还具有能源效率，并节省了95％以上的能量。
• USE OF COMPOSITIONS OBTAINED BY CALCINING PARTICULAR METAL-ACCUMULATING PLANTS FOR IMPLEMENTING CATALYTICAL REACTIONS
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：US20150376224A1

  公开（公告）日：2015-12-31

  The use of metal-accumulating plants for implementing chemical reactions especially catalytical reactions.

  金属积累植物用于实现化学反应，特别是催化反应的使用。
• 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。
• Highly convenient one-pot conversion of aryl acylals or aryl aldehyde bisulfites into dihydropyrimidones using BI(NO3)3⋅5H2O
  作者：Ahmad R. Khosropour、Mohammad M. Khodaei、Mojtaba Beygzadeh

  DOI：10.1002/hc.20352

  日期：2007.8

  A new, facile, and efficient one-pot deprotection–cyclocondensation method is presented for the Biginelli reaction from aryl acylals or aryl aldehyde bisulfites in the presence of catalytic amounts of Bi(NO3)3 ⋅ 5H2O under solvent-free conditions. In addition, high levels of chemoselectivity for this synthesis have been achieved. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:684–687, 2007; Published

  在无溶剂条件下，在催化量的 Bi(NO3)3 ⋅ 5H2O 存在下，芳酰基或芳醛亚硫酸氢盐的 Biginelli 反应，提出了一种新的、简便且有效的单锅脱保护-环缩聚方法。此外，该合成还实现了高水平的化学选择性。© 2007 Wiley Periodicals, Inc. 杂原子化学 18:684–687, 2007; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20352
• EFFICIENT AND GREEN CATALYTIC SYNTHESIS OF DIHYDROPYRIMIDINONE (THIONE) DERIVATIVES USING COBALT NITRATE IN SOLVENT-FREE CONDITIONS
  作者：MASOUD NASR-ESFAHANI、MORTEZA MONTAZEROZOHORI、MARYAM AGHEL-MIRREZAEE、HASSAN KASHI

  DOI：10.4067/s0717-97072014000100015

  日期：——

  environmentally friendly reaction conditions. Keywords: Dihydropyrimidinone, Dihydropyrimidinthione, Cobalt(II)Nitrate, Solvent-free, One-pot synthesis INTRODUCTION Synthesis of 3,4-dihydropyrimidine-2(1H)-Ones (DHPMs) through one-pot reaction of aromatic aldehyde, urea and ethyl acetoacetate in acid ethanol solution was initiated by Biginelli in 1893 1 . These compounds occupied an important place in medicinal

  摘要在无溶剂条件下，使用Co（NO 3）2 .6H 2 O合成了一系列3,4-二氢嘧啶-2（1H）-一（硫酮）衍生物。在导致经济途径的化学反应过程中避免有机溶剂是有效的。该反应的特征在于高效，短反应时间，高收率，简单的实验程序，催化剂的可获得性和环境友好的反应条件。关键词：二氢嘧啶酮，二氢嘧啶硫酮，硝酸钴（II），无溶剂，一锅法合成引言通过芳族醛，尿素和乙基的一锅法反应合成3,4-二氢嘧啶-2（1H）-一（DHPM） Biginelli于1893年发起了在酸性乙醇溶液中的乙酰乙酸酯1。这些化合物在药物和合成有机化学中占有重要地位，主要是因为它们具有广泛的生物活性2。值得注意的是，monastrol（1）是唯一可阻止哺乳动物细胞中正常双极纺锤体组装的细胞可渗透分子，从而导致细胞周期停滞