Ethyl 4-(3,4-difluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 205999-96-8

• 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 4-(3,4-difluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: ethyl 4-(3,4-difluorophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 205999-96-8
• 化学式: C₁₄H₁₄F₂N₂O₃
• 分子量: 296.274
• InChiKey: NEQWLXWXJHQCPL-UHFFFAOYSA-N

物化性质

• 熔点：
  185-186 °C
• 沸点：
  381.5±42.0 °C(Predicted)
• 密度：
  1.282±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  戊酸酐 、 Ethyl 4-(3,4-difluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以99%的产率得到Ethyl 4-(3,4-difluorophenyl)-6-methyl-2-oxo-3-pentanoyl-1,4-dihydropyrimidine-5-carboxylate
  参考文献：
  名称：

  High-Throughput Synthesis of N3-Acylated Dihydropyrimidines Combining Microwave-Assisted Synthesis and Scavenging Techniques

  摘要：

  The solution-phase synthesis of N3-acylated dihydropyrimidines was achieved utilizing microwave flash heating both in the synthesis (acylation) and purification (scavenging) steps. Quenching times for excess anhydrides using polystyrene or silica-supported diamine sequestration reagents were reduced from several hours to minutes utilizing microwave irradiation. The use of water as sequestration agent, coupled with an efficient solid-phase extraction workup technique allowed the rapid generation of a 20-member library of N3-acylated dihydropyrimidines.

  DOI：

  10.1021/ol034085v
• 作为产物：
  描述：

  3,4-二氟苯甲醛 、 乙酰乙酸乙酯 、 尿素 在 polyphosphate ester 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以84%的产率得到Ethyl 4-(3,4-difluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Polyphosphate Ester-Mediated Synthesis of Dihydropyrimidines. Improved Conditions for the Biginelli Reaction

  摘要：

  二氢嘧啶7通过醛、乙酰乙酸酯和脲在一锅法中使用聚磷酸酯介导的环缩合反应，以高产率制备。与传统的Biginelli反应条件相比，产率显著提高。

  DOI：

  10.1055/s-1998-1764

文献信息

• ENANTIOSELECTIVE SYNTHESIS OF DIHYDROPYRIMIDINONES AND HEXAHYDROPYRIMIDINONES
  申请人：Universitat de les Illes Balears

  公开号：EP3260446A1

  公开（公告）日：2017-12-27

  The present invention provides with a "one pot" easily scalable preparation process, or method to obtain enantiomerically enriched dihydropyrimidinones (DHPMs), in high yield and high enantiomeric purity, based on the concept of organocatalysis by a network of cooperative hydrogen bonds (NCHB). Said preparation process obtains enantiomerically enriched DHPMs without the use of metal-based catalysis and with the possibility of the recovery of the chiral organocatalyst comprising a NCHB used. The present invention also provides with new enantiomerically and diastereomerically enriched hexahydropyrimidinones (HHPMs), as well as a preparation process to obtain them also based on the concept of organocatalysis by a NCHB. Said preparation process obtains enantiomerically and diastereomerically enriched HHPMs without the use of metal-based catalysis and with the possibility of the recovery of the chiral organocatalyst comprising a NCHB used.

  本发明基于协同氢键网络（NCHB）有机催化的概念，提供了一种 "一锅式 "易扩展的制备工艺或方法，以高产率和高对映体纯度获得对映体富集的二氢嘧啶酮（DHPMs）。所述制备工艺无需使用金属催化，即可获得对映体富集的 DHPM，并有可能回收由所使用的 NCHB 组成的手性有机催化剂。本发明还提供了新的对映异构体和非对映异构体富集的六氢嘧啶酮（HHPMs），以及同样基于 NCHB 有机催化概念的获得它们的制备工艺。该制备工艺无需使用金属催化即可获得对映体和非对映异构体富集的六氢嘧啶酮（HHPMs），并有可能回收由所使用的 NCHB 组成的手性有机催化剂。
• Microwave-Assisted High-Speed Parallel Synthesis of 4-Aryl-3,4-dihydropyrimidin-2(1H)-ones using a Solventless Biginelli Condensation Protocol
  作者：C. Oliver Kappe

  DOI：10.1055/s-1999-3592

  日期：1999.10
• Unprecedented Catalytic Three Component One-Pot Condensation Reaction:  An Efficient Synthesis of 5-Alkoxycarbonyl- 4-aryl-3,4-dihydropyrimidin-2(1H)-ones
  作者：Essa H. Hu、Daniel R. Sidler、Ulf-H. Dolling

  DOI：10.1021/jo970846u

  日期：1998.5.1