(R)-5-ethoxycarbonyl-4-(4-chlorophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one | 1026791-58-1

• 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: (R)-5-ethoxycarbonyl-4-(4-chlorophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one
• 英文别名: (R)-5-ethoxycarbonyl-6-methyl-4-(4-chlorophenyl)-3,4-dihydropyrimidin-2(1H)-one；ethyl (4R)-4-(4-chlorophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 1026791-58-1
• 化学式: C₁₄H₁₅ClN₂O₃
• 分子量: 294.738
• InChiKey: JYWSCUFVWRZFDR-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 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：
  3

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 4-氯苯甲醛 、 尿素 在 C₁₂H₁₈CuN₆O₄⁽²⁺⁾*2Cl^(1-) 作用下， 以 neat (no solvent) 为溶剂， 反应 14.0h， 以90%的产率得到(R)-5-ethoxycarbonyl-4-(4-chlorophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  Development and efficient 1-glycyl-3-methyl imidazolium chloride–copper(II) complex catalyzed highly enantioselective synthesis of 3, 4-dihydropyrimidin-2(1H)-ones

  摘要：

  A novel, effective asymmetric 1-glycyl-3-methyl imidazolium chloride-copper(II) complex [[Gmim]Cl-Cu(II)] was synthesized and studied as organocatalyst for enantioselective Biginelli reaction under solvent free condition at 25 degrees C. The hydrophobic group on amino acid favors reagent diffusion towards the chloroglycine moiety increasing the catalytic activity of supported palladium complex. Spectroscopic evidence of complex has been proved by Powder XRD, SEM, FT-IR and AFM. This method contains simplified product isolation and catalyst recycling, affording substituted aldehydes imparting high yield with excellent stereoselectivity. This recyclable heterogeneous catalyst provides a simple strategy for the generation of a variety of new C-C bonds under environmentally benign condition. (C) 2012 Published by Elsevier B.V.

  DOI：

  10.1016/j.jorganchem.2012.06.022

文献信息

• Highly enantioselective Biginelli reaction catalyzed by a simple chiral primary amine catalyst: asymmetric synthesis of dihydropyrimidines
  作者：Da-Zhen Xu、Hui Li、Yongmei Wang

  DOI：10.1016/j.tet.2012.07.027

  日期：2012.9

  Several chiral primary amines were introduced as organocatalysts for the asymmetric Biginelli reaction. The reaction was performed by using a combined catalyst consisting of a chiral bifunctional primary amine–pyridine 5j and hydrochloric acid in a mixed solvent of 1,4-dioxane/CHCl3 (8/2, v/v) at room temperature. The corresponding dihydropyrimidines were obtained in moderate to high yields with up

  几种手性伯胺被引入作为不对称Biginelli反应的有机催化剂。反应是在室温下，使用由手性双官能伯胺-吡啶5j和盐酸组成的混合催化剂在1,4-二恶烷/ CHCl 3（8/2，v / v）的混合溶剂中进行的。在温和条件下，以中等至高收率获得了相应的二氢嘧啶，其中ee高达> 99％。
• 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。
• Bifunctional primary amine-thiourea–TfOH (BPAT·TfOH) as a chiral phase-transfer catalyst: the asymmetric synthesis of dihydropyrimidines
  作者：Yangyun Wang、Jipan Yu、Zhiwei Miao、Ruyu Chen

  DOI：10.1039/c0ob01268h

  日期：——

  An enantioselective Biginelli reaction has been developed by using a bifunctional primary amine-thiourea–TfOH (BPAT·TfOH) as a chiral phase-transfer catalyst and t-BuNH2·TFA as an additive in saturated brine at room temperature. The corresponding dihydropyrimidines were obtained in moderate-to-good yields with up to 99% ee under mild conditions. A plausible transition state has been proposed to explain the origin of the activation and the asymmetric induction.

  在室温饱和盐水中，使用双功能伯胺-硫脲-TfOH（BPATÂ-TfOH）作为手性相转移催化剂和 t-BuNH2Â-TFA 作为添加剂，开发了一种对映体选择性 Biginelli 反应。在温和的条件下，得到了相应的二氢嘧啶，收率从中等到良好，ee高达 99%。研究人员提出了一种可信的过渡态来解释活化和不对称诱导的起源。
• Cooperative and Enantioselective NbCl5/Primary Amine Catalyzed Biginelli Reaction
  作者：Yong-Feng Cai、Hua-Meng Yang、Li Li、Ke-Zhi Jiang、Guo-Qiao Lai、Jian-Xiong Jiang、Li-Wen Xu

  DOI：10.1002/ejoc.201000894

  日期：2010.9

  evaluated in the Lewis acid/organocatalysts-based cooperative catalytic Biginelli reaction, which resulted in the determination of a novel cooperative Lewis acid/primary amine catalyst system, NbCl5/QN-NH2. The synergistic effect of NbCl5 and the quinine-derived primary amine is pronounced and gave dihydropyrimidiones (DHPMs) in moderate to good enantioselectivities (up to 84 % ee) and good to excellent yields

  在基于路易斯酸/有机催化剂的协同催化 Biginelli 反应中评估了一系列手性有机催化剂和路易斯酸，从而确定了一种新型的路易斯酸/伯胺协同催化剂体系 NbCl5/QN-NH2。NbCl5 和奎宁衍生的伯胺的协同作用是显着的，在温和的条件下以中等至良好的对映选择性（高达 84% ee）和良好至极好的产率（产率高达 99%）得到二氢嘧啶酮 (DHPM)。
• Development and efficient 1-glycyl-3-methyl imidazolium chloride–copper(II) complex catalyzed highly enantioselective synthesis of 3, 4-dihydropyrimidin-2(1H)-ones
  作者：Parasuraman Karthikeyan、Sachin Arunrao Aswar、Prashant Narayan Muskawar、Pundlik Rambhau Bhagat、S. Senthil Kumar

  DOI：10.1016/j.jorganchem.2012.06.022

  日期：2013.1

  A novel, effective asymmetric 1-glycyl-3-methyl imidazolium chloride-copper(II) complex [[Gmim]Cl-Cu(II)] was synthesized and studied as organocatalyst for enantioselective Biginelli reaction under solvent free condition at 25 degrees C. The hydrophobic group on amino acid favors reagent diffusion towards the chloroglycine moiety increasing the catalytic activity of supported palladium complex. Spectroscopic evidence of complex has been proved by Powder XRD, SEM, FT-IR and AFM. This method contains simplified product isolation and catalyst recycling, affording substituted aldehydes imparting high yield with excellent stereoselectivity. This recyclable heterogeneous catalyst provides a simple strategy for the generation of a variety of new C-C bonds under environmentally benign condition. (C) 2012 Published by Elsevier B.V.