5-methoxycarbonyl-6-methyl-4-(4-methylphenyl)-3,4-dihydropyrimidin-2(1H)-one | 193623-15-3

• 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: 5-methoxycarbonyl-6-methyl-4-(4-methylphenyl)-3,4-dihydropyrimidin-2(1H)-one
• 英文别名: methyl 6-methyl-2-oxo-4-(p-tolyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate；Methyl 6-methyl-4-(4-methylphenyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate；methyl 6-methyl-4-(4-methylphenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 193623-15-3
• 化学式: C₁₄H₁₆N₂O₃
• 分子量: 260.293
• InChiKey: DKVKSVGPBRENPW-UHFFFAOYSA-N

物化性质

• 熔点：
  203 °C(Solv: methanol (67-56-1))
• 沸点：
  390.5±42.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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-(4-methylphenyl)-3,4-dihydropyrimidin-2(1H)-one 生成 methyl (4S)-6-methyl-4-(4-methylphenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
  参考文献：
  名称：

  Separation of enantiomers of 4-aryldihydropyrimidines by direct enantioselective HPLC. A critical comparison of chiral stationary phases

  摘要：

  The separation of the enantiomers of 29 racemic 4-aryldihydropyrimidine-5-carboxylates (DHPMs), aza-analogs of nifedipine-type dihydropyridine calcium channel modulators, was evaluated in direct enantioselective HPLC, employing the following commercially available chiral stationary phases (CSPs): Chiralcel OD-H, ChiraDex, Chirobiotic V and T, and Whelk-O1. In addition, a 1,2-diphenyl-1,2-diaminoethane based CSP and two quinine carbamate based chiral ion exchangers were also employed. For all 29 DHPMs separation of individual enantiomers could be achieved with at least one CSP with alpha-values ranging from 1.10 to 8.67. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00214-0
• 作为产物：
  描述：

  对甲基苯甲醛 、 乙酰乙酸甲酯 、 尿素 在 dioxide titanium 作用下， 反应 0.58h， 以97%的产率得到5-methoxycarbonyl-6-methyl-4-(4-methylphenyl)-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  TiO2作为无溶剂条件下一锅合成3,4-二氢嘧啶-2（1H）-one的可重复使用催化剂

  摘要：

  描述了一种有效的无溶剂方法，该方法使用TiO 2作为可循环的非均相催化剂来合成各种3,4-二氢嘧啶-2（1 H）- 。与已知方法相比，以令人满意的产率，短的反应时间和简单的实验步骤获得了满意的结果。

  DOI：

  10.1002/hlca.200900197

文献信息

• 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 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。
• 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
• 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
• New environmentally friendly solvent free synthesis of dihydropyrimidinones catalysed by N-butyl-N,N-dimethyl-α-phenylethylammonium bromide
  作者：K. Rosi Reddy、Ch. Venkateshwar Reddy、M. Mahesh、P.V.K. Raju、V.V. Narayana Reddy

  DOI：10.1016/j.tetlet.2003.09.030

  日期：2003.10

  N-Butyl-N,N-dimethyl-α-phenylethylammonium bromide catalyzes efficiently the three component condensation reaction of an aromatic aldehyde, a β-keto ester and urea/thiourea under solvent free conditions at 100°C to afford the corresponding dihydropyrimidinone in high yield.

  N-丁基-N，N-二甲基-α-苯基乙基溴化铵可在无溶剂条件下于100°C下有效催化芳族醛，β-酮酸酯和脲/硫脲的三组分缩合反应，从而得到相应的二氢嘧啶酮屈服。