ethyl (R)-4-(4-cyanophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 1146289-76-0

• 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 (R)-4-(4-cyanophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: (R)-4-(4-cyanophenyl)-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(1H)-one；5-ethoxycarbonyl-6-methyl-4-(4-cyanophenyl)-3,4-dihydropyrimidin-2(1H)-one；ethyl (4R)-4-(4-cyanophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 1146289-76-0
• 化学式: C₁₅H₁₅N₃O₃
• 分子量: 285.302
• InChiKey: ISVGNXDVNJTYSD-CYBMUJFWSA-N

物化性质

• 熔点：
  181 °C
• 沸点：
  449.5±45.0 °C(predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  91.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  [(4-Cyanophenyl)-(4-methylphenyl)sulfonylmethyl]urea 、 乙酰乙酸乙酯 在 N,N-二异丙基乙胺 、 (1R,2R)-N,N’-di(2-hydroxybenzyl)-1,2-diaminocyclohexane 、 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 20.0h， 以84%的产率得到
  参考文献：
  名称：

  迈向类酶的可持续催化：对映纯比吉内利二氢嘧啶酮或六氢嘧啶酮的可转换，高效不对称合成

  摘要：

  具有协同氢键网络（NCHB）的有机催化剂已以类似酶的方式用于直接，可转换的对映纯六氢嘧啶酮（HHPM）或二氢嘧啶酮（DHPM）的合成，其起始于常见的易于获得的α-脲基砜阶段。NCHB有机催化剂即使在存在有机碱的情况下，也可以发挥其作为纯氢键仿生催化剂的全部潜力。这种单锅，非对映和对映选择性合成方法已被证明是可靠，可扩展，高效且对环境无害的。首次报道了一种直接，真正实用的对映纯HHPMs。

  DOI：

  10.1002/chem.201604433

文献信息

• Synthesis of Substituted 5-(Pyrrolidin-2-yl)tetrazoles and Their Application in the Asymmetric Biginelli Reaction
  作者：Yong-Yong Wu、Zhuo Chai、Xin-Yuan Liu、Gang Zhao、Shao-Wu Wang

  DOI：10.1002/ejoc.200801046

  日期：2009.2

  A series of chiral substituted 5-(pyrrolidin-2-yl)tetrazoles have been synthesized and evaluated as organocatalysts for the asymmetric Biginelli reaction. The relationship between catalytic activity and the different catalyst structures is briefly discussed. By using the optimized catalyst C10 (10 mol-%), a series of 3,4-dihydropyrimidin-2(1H)-one (DHPM) derivatives have been obtained in 63–88 % yields

  一系列手性取代的 5-（吡咯烷-2-基）四唑已被合成并评估为不对称 Biginelli 反应的有机催化剂。简要讨论了催化活性与不同催化剂结构之间的关系。通过使用优化的催化剂 C10 (10 mol-%)，在 24 分钟内以 63-88% 的产率和 68-81% 的 ee 值获得了一系列 3,4-二氢嘧啶-2(1H)-酮 (DHPM) 衍生物。 h 在室温下。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Primary Amine Catalyzed Biginelli Reaction for the Enantioselective Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones
  作者：Derong Ding、Cong-Gui Zhao

  DOI：10.1002/ejoc.201000448

  日期：——

  Several chiral primary amines, mainly those derived from the cinchona alkaloids, were evaluated as the organocatalysts for the asymmetric Biginelli reaction. With the quinine-derived amine catalyst 1 and after extensive optimization of the reaction conditions, 3,4-dihydropyrimidin-2(1H)-ones were obtained in moderate to good yields and 51-78% ee from a three-component reaction of aryl and aliphatic

  几种手性伯胺，主要来自金鸡纳生物碱，被评估为不对称 Biginelli 反应的有机催化剂。使用奎宁衍生的胺催化剂 1 和反应条件的广泛优化后，3,4-二氢嘧啶-2(1H)-酮以中等至良好的收率和 51-78% ee 从芳基的三组分反应中获得和脂肪醛、尿素和乙酰乙酸酯。
• 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。
• Enantioselective Organocatalytic Biginelli Reaction: Dependence of the Catalyst on Sterics, Hydrogen Bonding, and Reinforced Chirality
  作者：Satyajit Saha、Jarugu Narasimha Moorthy

  DOI：10.1021/jo101717m

  日期：2011.1.21

  From a systematic investigation involving the synthesis of a series of catalysts and screening studies, the organocatalyst 16, which is sterically hindered, contains a strong hydrogen-bonding site, and is endowed with reinforced chirality, is shown to promote the Biginelli cyclocondensation of aromatic as well as aliphatic aldehydes with ethyl acetoacetate and urea in a remarkably high enantioselectivity (ee ca. 94-99%).