ethyl 6-methyl-4(fur-2-yl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 123629-40-3

• 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: ethyl 6-methyl-4(fur-2-yl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: (±)-ethyl 4-(furan-2-yl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；(±)-ethyl-4-(furan-2-yl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；4-(2-furyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester；ethyl 4-(furan-2-yl)-1,2,3,4-tetrahydro-6-methyl-2-oxopyrimidine-5-carboxylate；ethyl 4-(furan-2-yl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；ethyl 4-(2-furanyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate；ethyl 4-(furan-2-yl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 123629-40-3
• 化学式: C₁₂H₁₄N₂O₄
• 分子量: 250.254
• InChiKey: IQIGXCCKCMDVJZ-UHFFFAOYSA-N

物化性质

• 熔点：
  202-204 °C
• 沸点：
  365.3±42.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 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：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 6-methyl-4(fur-2-yl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 在 1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate 、 水 作用下， 以 乙腈 为溶剂， 反应 1.42h， 以90%的产率得到ethyl 6-methyl-4-(2-furyl)pyrimidin-2(1H)-one-5-carboxylate
  参考文献：
  名称：

  Novel and Chemoselective Dehydrogenation of 3,4-Dihydropyrimidin-2(1H)-ones with 1,4-Bis(triphenylphosphonium)-2-butene Peroxodisulfate

  摘要：

  3,4-二氢嘧啶-2(1H)-酮在1,4-双(三苯基膦)-2-丁烯过硫酸盐水溶液乙腈中处理下，短时间内高效转化为相应的嘧啶-2(1H)-酮，产率很高。该试剂还能在其他可氧化官能团的存在下实现3,4-二氢嘧啶的选择性氧化。

  DOI：

  10.5012/bkcs.2013.34.6.1751
• 作为产物：
  描述：

  6-甲基-2-氧代-1,2,3,4-四氢嘧啶-5-羧酸乙酯 在 正丁基锂 、 硝酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 ethyl 6-methyl-4(fur-2-yl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  A highly regio- and chemoselective addition of carbon nucleophiles to pyrimidinones. A new route to C4 elaborated Biginelli compounds

  摘要：

  Ethyl 6-methyl-pyrimidine-2-one-5-carboxylates react with C-nucleophiles in a diversity oriented synthetic sequence to afford C4 substituted congeners of medicinally potent Biginelli dihydropyrimidinones, in a highly regioselective manner. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.12.111

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 One-Pot Synthesis of 3,4-Dihydropyrimidin-2-(1H)-ones from Primary Alcohols Promoted by Bi(NO3)3·5H2O in Two Different Media: Organic Solvent and Ionic Liquid
  作者：Ahmad Reza Khosropour、Ahmad R. Khosropour、Mohammd M. Khodaei、Mojtaba Beygzadeh、Mahbubeh Jokar

  DOI：10.3987/com-04-10257

  日期：——

  A new, simple and efficient procedure for the one-pot conversion of alcohols instead of aldehydes to the corresponding 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) with Bi(NO 3 ) 3 .5H 2 O as a commercially available, inexpensive, stable and non-toxic reagent in two media, acetonitrile (as an organic solvent) and tetrabutylammonium bromide (as an ionic liquid) is described. This one-pot oxidation-cyclocondensation

  一种新的、简单且有效的方法，用于将醇而不是醛一锅转化为相应的 3,4-二氢嘧啶-2(1H)-酮 (DHPM)，其中 Bi(NO 3 ) 3 .5H 2 O 作为商业应用描述了在乙腈（作为有机溶剂）和四丁基溴化铵（作为离子液体）这两种介质中可获得、廉价、稳定和无毒的试剂。这种一锅氧化-环缩合反应无需分离任何中间体（醛）即可进行，从而缩短了时间，节省了能源和原材料。另一方面，用这种新的一锅法处理伯醇产生的脱氢嘧啶酮的产率高于传统方法中的产率。
• A facile approach for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones using a microwave promoted Biginelli protocol in ionic liquid
  作者：ABHISHEK N DADHANIA、VAIBHAV K PATEL、DIPAK K RAVAL

  DOI：10.1007/s12039-012-0278-5

  日期：2012.7

  recycled and reused in at least six subsequent reactions with consistent activity. Carboxy functionalized ionic liquid [cmmim][BF4] is shown to be an efficient and green catalyst for the one pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones heterocycles under microwave irradiation. This methodology represents an easy access to Biginelli compounds with high yields and purity. The ionic liquid was recycled

  羧基官能化的离子液体[cmmim] [BF 4 ]已被证明是在微波辐射下一锅合成3,4-二氢嘧啶-2-（1 H）-一个杂环的高效绿色催化剂。离子液体微波策略可以轻松获得具有高收率和纯度的Biginelli化合物。发现该方案与不同结构上不同的醛相容。离子液体被循环使用，并在至少六个随后的具有一致活性的反应中重新使用。 羧基官能化的离子液体[cmmim] [BF 4 ]被证明是在微波辐射下一锅合成3,4-二氢嘧啶-2-（1 H）-ones杂环的高效绿色催化剂。这种方法论代表了容易获得高收率和高纯度的比吉内利化合物的方法。离子液体被回收利用，结果一致。
• 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
• Synthesis of 3,4-dihydropyrimidin-2(1H)-ones and 1,4-dihydropyridines using ammonium carbonate in water
  作者：Fatemeh Tamaddon、Zahra Razmi、Abbas Ali Jafari

  DOI：10.1016/j.tetlet.2009.12.098

  日期：2010.2

  known and new 3,4-dihydropyrimidin-2(1H)-ones and 1,4-dihydropyridines are prepared efficiently via Biginelli and Hantzsch reactions using ammonium carbonate in water. Competition between Biginelli and Hantzsch reactions is observed with pyridine carbaldehydes. Using this methodology, Hantzsch esters are synthesized in higher yields and purities than with other procedures without the use of a catalyst

  通过Biginelli和Hantzsch反应，使用碳酸铵在水中有效地制备了各种已知的和新的3,4-二氢嘧啶-2（1 H）-酮和1,4-二氢吡啶。用吡啶甲醛观察到Biginelli反应和Hantzsch反应之间的竞争。使用这种方法，无需使用催化剂或有机溶剂，即可比其他方法以更高的收率和纯度合成汉茨酯。