(±)-isopropyl 4-(2-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 312596-19-3

• 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: (±)-isopropyl 4-(2-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: 5-isopropoxycarbonyl-4-(2'-chlorophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one；isopropyl 4-(2-chlorophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate；propan-2-yl 4-(2-chlorophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 312596-19-3
• 化学式: C₁₅H₁₇ClN₂O₃
• 分子量: 308.765
• InChiKey: PIBPZYSVASLCQT-UHFFFAOYSA-N

物化性质

• 熔点：
  224-226 °C(Solv: ethanol (64-17-5))
• 沸点：
  406.0±45.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙酰乙酸异丙酯 、 2-氯苯甲醛 、 尿素 在 calcium fluoride 作用下， 以 乙醇 为溶剂， 反应 1.3h， 以96%的产率得到(±)-isopropyl 4-(2-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  氟化钙：一种有效且可重复使用的催化剂，用于合成3,4-二氢嘧啶-2（1 H）-及其相应的2（1 H）硫酮：Biginelli反应的改进的高产方案

  摘要：

  已经描述了通过使用氟化钙作为催化剂，在乙醇中从醛，1，3-二羰基化合物和脲/硫脲简单而有效地合成3，4-二氢嘧啶酮衍生物。与经典的Biginelli反应条件相比，该新方法具有优异的收率和较短的反应时间的优点。而且，催化剂可以在不降低效率的情况下重复使用。

  DOI：

  10.1016/j.tetlet.2009.02.162

文献信息

• Exploring the influence of the substituent at position 4 in a series of 3,4-dihydropyrimidin-2(1H)-one A2B adenosine receptor antagonists
  作者：Abel Crespo、Abdelaziz El Maatougui、Jhonny Azuaje、Luz Escalante、María Majellaro、María Isabel Loza、José Brea、María Isabel Cadavid、Hugo Gutiérrez-de-Terán、Eddy Sotelo

  DOI：10.1007/s10593-017-2054-4

  日期：2017.3

  identify selective adenosine A2B receptor antagonists, we have obtained a focused library of 4-substituted 3,4-dihydropyrimidin-2(1H)-ones and its affinity for the four human adenosine receptor subtypes was determined. The synthesis was accomplished by using an experimentally simple and efficient Biginelli approach. The biological evaluation of the library revealed that all the documented derivatives exhibit

  在鉴定选择性腺苷A2B受体拮抗剂的计划的背景下，我们获得了一个4位取代的3,4-二氢嘧啶-2（1 H）-ones的库，并确定了其对四种人腺苷受体亚型的亲和力。该合成是通过使用实验简单有效的Biginelli方法完成的。对文库的生物学评估表明，所有已记录的衍生物对A 2B受体的亲和力均较低或可忽略不计，因此突出了3,4-二氢嘧啶-2（1 H）-一种化学型中4位取代基的至关重要性。。
• Synthesis and in vitro microbiological evaluation of novel 4-aryl-5-isopropoxycarbonyl-6-methyl-3,4-dihydropyrimidinones
  作者：S. Chitra、D. Devanathan、K. Pandiarajan

  DOI：10.1016/j.ejmech.2009.09.018

  日期：2010.1

  Seven 4-aryl-5-isopropoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(1H)-ones 4a-g and 4-phenyl-5-isopropoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(1H)-thione 4h have been synthesized by a one-pot cyclocondensation of aldehydes, isopropyl acetoacetate and urea/thiourea in ethanol by using strontium chloride hexahydrate as the catalyst. All the compounds were screened for their antibacterial activity against Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa and Salmonella typhi and antifungal activity against Candida albicans, Aspergillus flavus. Rhizopus and Mucor. Compounds 4b, 4c, 4f, 4g exhibited excellent in vitro antibacterial activity against Staphylococcus aureus, Salmonella typhi and Pseudomonas aeruginosa and potent in vitro antifungal activity against Candida albicans, Rhizopus and Mucor. Compound 4f with a nitro group at the para position of the 4-aryl group and 4g with a fluorine at the para position of the 4-aryl group showed more activity than the standard drugs. (C) 2009 Elsevier Masson SAS. All rights reserved.
• Calcium fluoride: an efficient and reusable catalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones and their corresponding 2(1H)thione: an improved high yielding protocol for the Biginelli reaction
  作者：S. Chitra、K. Pandiarajan

  DOI：10.1016/j.tetlet.2009.02.162

  日期：2009.5

  A simple and effective synthesis of 3,4-dihydropyrimidinone derivatives from aldehydes, 1,3-dicarbonyl compounds, and urea/thiourea in ethanol by using calcium fluoride as catalyst has been described. Compared with classical Biginelli reaction conditions, this new method has the advantage of excellent yields and shorter reaction times. Also, the catalyst can be reused without any reduction in efficiency

  已经描述了通过使用氟化钙作为催化剂，在乙醇中从醛，1，3-二羰基化合物和脲/硫脲简单而有效地合成3，4-二氢嘧啶酮衍生物。与经典的Biginelli反应条件相比，该新方法具有优异的收率和较短的反应时间的优点。而且，催化剂可以在不降低效率的情况下重复使用。