ethyl 6-methyl-4-(5-methylfuran-2-yl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

• 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: ethyl 6-methyl-4-(5-methylfuran-2-yl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: 5-ethoxycarbonyl-4-(5-methyl-2-furyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one；Ethyl 2-hydroxy-4-methyl-6-(5-methylfuran-2-yl)-1,6-dihydropyrimidine-5-carboxylate；ethyl 6-methyl-4-(5-methylfuran-2-yl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₁₃H₁₆N₂O₄
• 分子量: 264.281
• InChiKey: QWVIOSJFVHTZTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-甲基呋喃醛 、 乙酰乙酸乙酯 、 尿素 在 TS-1 zeolite 作用下， 反应 0.25h， 以95%的产率得到ethyl 6-methyl-4-(5-methylfuran-2-yl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  沸石催化无溶剂一锅法合成二氢嘧啶-2(1H)-ones——一种实用的monastrol合成方法。

  摘要：

  描述了一种沸石催化、简单、单锅、无溶剂、成本有效且环境友好的合成二氢嘧啶酮的方法。该反应可扩展到数克规模，并且催化剂可回收利用。这种方法导致了monastrol的有效合成，monastrol是驱动蛋白Eg5的有效抑制剂。

  DOI：

  10.3762/bjoc.5.4

文献信息

• A Brønsted acid catalysed enantioselective Biginelli reaction
  作者：Margherita Barbero、Silvano Cadamuro、Stefano Dughera

  DOI：10.1039/c6gc03274e

  日期：——

  chiral derivative of 1,2-benzenedisulfonimide, namely (-)-4,5-dimethyl-3,6-bis(o-tolyl)-1,2-benzenedisulfonimide is herein proven to be an efficient chiral catalyst in a one pot three-component Biginelli reaction. In fact the yields of the target...

  1，2-苯二磺酰亚胺的手性衍生物，即（-）-4,5-二甲基-3,6-双（邻甲苯基）-1，2-苯二磺酰亚胺在本文中被证明是一种有效的手性催化剂三组分Biginelli反应。实际上目标的产量...
• Sulfated Zirconia-Catalyzed Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones (DHPMs) Under Solventless Conditions: Competitive Multicomponent Biginelli vs. Hantzsch Reactions
  作者：Deyanira Angeles-Beltrán、Leticia Lomas-Romero、Victor Lara-Corona、Eduardo González-Zamora、Guillermo Negrón-Silva

  DOI：10.3390/11100731

  日期：——

  The catalytic ability of ZrO2/SO42- to promote solventless three-componentcondensation reactions of a diversity of aromatic aldehydes, urea or thoiurea and ethylacetoacetate was studied. Products resulting from Hantzsch and/or Biginelli multi-component reactions are obtained in the presence of solid acid catalysts using the samereactants but different temperature conditions. The sulfated zirconia catalyst can berecovered and recycled in subsequent reactions with a gradual decrease of activity.

  研究了ZrO2/SO42-对多种芳香醛、尿素或硫脲与乙酰乙酸乙酯无溶剂三组分缩合反应的催化能力。由 Hantzsch 和/或 Biginelli 多组分反应产生的产物是在固体酸催化剂存在下使用相同的反应物但不同的温度条件获得的。硫酸化氧化锆催化剂可在后续反应中回收并循环使用，活性逐渐降低。
• Zn2+/MCM-41 catalyzed Biginelli reaction of heteroaryl aldehydes and evaluation of the antimicrobial activity and cytotoxicity of the pyrimidone products
  作者：Zarrin Ghasemi、Farzaneh Farshbaf Orafa、Mahtab Pirouzmand、Gholamreza Zarrini、Behnaz Nikzad Kojanag、Roya Salehi

  DOI：10.1016/j.tetlet.2015.09.143

  日期：2015.11

  The three component Biginelli condensation of various aryl aldehydes, 1,3-dicarbonyls and urea was investigated in the presence of free or MCM-41 supported ZnNO3. The pyrimidone products, which were obtained under solvent-free conditions, were evaluated for antibacterial and antifungal activities as well as their cytotoxicities. (C) 2015 Elsevier Ltd. All rights reserved.
• 3,4-Hydropyrimidin-2-(1H)one derivatives: solid silica-based sulfonic acid catalyzed microwave-assisted synthesis and their biological evaluation as antihypertensive and calcium channel blocking agents
  作者：Srinivasa Rao Jetti、Amitbodh Upadhyaya、Shubha Jain

  DOI：10.1007/s00044-014-0988-y

  日期：2014.10

  Microwave assisted simple, efficient procedure for one-pot Biginelli condensation reaction of aldehydes, beta-ketoesters, and urea or thiourea in solvent-free condition employing solid silica-based sulfonic acid as a novel, heterogeneous reusable catalyst is described. Compared to the classical Biginelli reaction conditions, the present method has the advantages of good yields, short reaction times, and experimental simplicity. The newly synthesized compounds have been screened to in vitro antihypertensive and calcium channel blocking activity done by IC50 measurement method with nifedipine as standard.
• Yadav, Kalpana; Dhadda, Surbhi; Guleria, Anjali, Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 2020, vol. 59, # 1, p. 102 - 109
  作者：Yadav, Kalpana、Dhadda, Surbhi、Guleria, Anjali、Goswami, Prakash Giri、Khandelwal, Chandralata、Jangid, Dinesh Kumar

  DOI：——

  日期：——