5-methoxycarbonyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one | 188780-24-7

• 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: 5-methoxycarbonyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one
• 英文别名: 5-methoxycarbonyl-4-phenyl-6-methyl-3,4-dihydropyrimidin-2(1H)-one；methyl 6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate；methyl 1,2,3,4-tetrahydro-6-methyl-2-oxo-4-phenylpyrimidine-5-carboxylate；methyl 6-methyl-2-oxo-4-phenyl-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 188780-24-7
• 化学式: C₁₃H₁₄N₂O₃
• 分子量: 246.266
• InChiKey: ZZQDAVSMSTUQAQ-UHFFFAOYSA-N

物化性质

• 熔点：
  209-212 °C
• 沸点：
  373.5±42.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  5-methoxycarbonyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 1,2,3,4-四氢-6-甲基-2-氧代-4-苯基-5-嘧啶羧酸
  参考文献：
  名称：

  Expedient synthesis of 5-unsubstituted 3,4-dihydropyrimidin-2(1H)-ones

  摘要：

  A new procedure for the synthesis of 5-unsubstituted 3,4-dihydropyrimidin-2(1H)-ones is described. Two plausible mechanisms for the key chemical transformation are advanced. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02155-8
• 作为产物：
  描述：

  6-甲基-2-氧代-4-苯基-1,2-二氢嘧啶-5-羧酸甲酯 在 碘 、 magnesium 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以64%的产率得到5-methoxycarbonyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  镁/甲醇：一种化学选择性还原嘧啶-2（1 H）-ones的有效还原剂

  摘要：

  甲醇中的镁是化学选择性还原嘧啶2（1 H）-ones的有效试剂。其他可还原的官能团，例如烯胺酯和乌里多羰基的酯和烯烃，不受影响。这构成了通过嘧啶-2（1 H）-one的还原形成Biginelli 3,4-dihydropyrimidin-2（1 H）one的第一个例子。

  DOI：

  10.1016/j.tetlet.2009.02.165

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。
• One Pot Synthesis of Micromolar BACE-1 Inhibitors Based on the Dihydropyrimidinone Scaffold and Their Thia and Imino Analogues
  作者：Jessica Bais、Fabio Benedetti、Federico Berti、Iole Cerminara、Sara Drioli、Maria Funicello、Giorgia Regini、Mattia Vidali、Fulvia Felluga

  DOI：10.3390/molecules25184152

  日期：——

  A library of dihydropyrimidinones was synthesized via a “one-pot” three component Biginelli reaction using different aldehydes in combination with β-dicarbonyl compounds and urea. Selected 2-thiooxo and 2-imino analogs were also obtained with the Biginelli reaction from thiourea and guanidine hydrochloride, respectively. The products were screened in vitro for their β-secretase inhibitory activity. The majority of the compounds resulted to be active, with IC50 in the range 100 nM–50 μM.

  通过使用不同的醛与β-二羰基化合物和尿素的“一锅法”三组分Biginelli反应合成了一系列二氢嘧啶酮类化合物。选择性地，也从硫脲和盐酸胍得到了2-硫氧代和2-亚氨基类似物。这些产物在体外被筛选，用于评估它们的β-分泌酶抑制活性。大多数化合物表现出活性，IC50在100 nM至50 μM范围内。
• Preyssler heteropolyacid supported on silica coated NiFe2O4 nanoparticles for the catalytic synthesis of bis(dihydropyrimidinone)benzene and 3,4-dihydropyrimidin-2(1H)-ones
  作者：Hossein Eshghi、Ali Javid、Amir Khojastehnezhad、Farid Moeinpour、Fatemeh F. Bamoharram、Mehdi Bakavoli、Masoud Mirzaei

  DOI：10.1016/s1872-2067(14)60265-5

  日期：2015.3

  Abstract A novel magnetic acidic catalyst comprising Preyssler (H 14 [NaP 5 W 30 O 110 ]) heteropoly acid supported on silica coated nickel ferrite nanoparticles (NiFe 2 O 4 @SiO 2 ) was prepared. The catalyst was characterized by Fourier transform infrared, scanning electron microscopy, transmission electron microscopy, X-ray diffraction, energy dispersive spectrum, VSM and particle size neasurement

  摘要 制备了一种新型磁性酸性催化剂，其包含负载在二氧化硅包覆的铁氧体镍纳米颗粒（NiFe 2 O 4 @SiO 2 ）上的 Preyssler (H 14 [NaP 5 W 30 O 110 ]) 杂多酸。通过傅里叶变换红外光谱、扫描电镜、透射电镜、X射线衍射、能谱、VSM和粒度测定对催化剂进行了表征。通过Biginelli反应研究了其在合成双(二氢嘧啶酮)苯和3,4-二氢嘧啶-2(1 H)-酮衍生物中的催化活性。使用催化剂，反应在不到 1 小时内发生，产率非常好。更重要的是，催化剂很容易通过外部磁铁从反应混合物中分离出来，并且可以重复使用至少五次而不会降低活性。
• A green approach for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones (and -thiones) using N,N-diethyl-N-sulfoethanaminium hydrogen sulfate
  作者：Abdolkarim Zare、Zahra Nasouri

  DOI：10.1016/j.molliq.2016.01.056

  日期：2016.4

  synthesized, and characterized by studying its FT-IR, 1H NMR, 13C NMR and mass spectra. Afterward, catalytic activity of the Brønsted acidic ionic liquid has been examined for the preparation of 3,4-dihydropyrimidin-2-(1H)-ones and 3,4-dihydropyrimidin-2-(1H)-thiones via the one-pot multi-component reaction between arylaldehydes, β-ketoesters and urea (or -thiourea) under solvent-free conditions. The

  本文合成了一种新型的含SO 3 H的离子液体，即N，N-二乙基-N-磺基硫代硫酸氢铵（[Et 3 N–SO 3 H] HSO 4），并对其FT-IR进行了表征。 ，1 H NMR，13 C NMR和质谱。此后，已经检查了布朗斯台德酸性离子液体的催化活性，用于通过以下方法制备3,4-二氢嘧啶-2-（1 H）-酮和3,4-二氢嘧啶-2-（1 H）-硫酮。在无溶剂条件下，芳基醛，β-酮酸酯与尿素（或-硫脲）之间的一锅多组分反应。结果表明，[Et 3 N–SO 3 H] HSO 4是该反应的高效催化剂。
• 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