(R)-(-)-5-ethoxycarbonyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-thione

• 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-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-thione
• 英文别名: ethyl 6-methyl-4-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；(R)-Ethyl 6-methyl-4-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；ethyl (4R)-6-methyl-4-phenyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₁₄H₁₆N₂O₂S
• mdl: MFCD00188414
• 分子量: 276.359
• InChiKey: QMFBVGUFEGVPNG-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 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：
  82.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-chloro-N-(4-(3-(3,4,5-trimethoxyphenyl)acryloyl)phenyl)acetamide 、 (R)-(-)-5-ethoxycarbonyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-thione 在 potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以85 %的产率得到ethyl (R,E)-6-methyl-2-((2-oxo-2-((4–(3-(3,4,5-trimethoxyphenyl)acryloyl)phenyl)amino)ethyl)thio)-4-phenyl-1,4-dihydropyrimidine-5-carboxylate
  参考文献：
  名称：

  10.1080/14756366.2024.2358934

  摘要：

  DOI：

  10.1080/14756366.2024.2358934
• 作为产物：
  描述：

  6-甲基-4-苯基-2-硫代-1,2,3,4-四氢嘧啶-5-羧酸乙酯 生成 (R)-(-)-5-ethoxycarbonyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-thione
  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

文献信息

• Solution-phase synthesis and evaluation of tetraproline chiral stationary phases
  作者：Zhi Dai、Guozhong Ye、Charles U. Pittman、Tingyu Li

  DOI：10.1002/chir.22001

  日期：2012.4

  solution‐phase synthesis of multigram amounts of two 9‐fluorenylmethoxycarbonyl (Fmoc)‐protected tetraproline peptides. These tetraproline peptides were then attached to amino derivatized silica gel. The replacement of the Fmoc group with the trimethylacetyl group lead to two tetraproline chiral stationary phases (CSPs). A comparison of the chromatographic behavior of these two solution‐phase‐synthesized

  开发了一种协议方案，用于溶液相合成多克数量的两个9-芴基甲氧基羰基（Fmoc）保护的四脯氨酸肽。然后将这些四脯氨酸肽连接到氨基衍生的硅胶上。用三甲基乙酰基取代Fmoc基团会导致两个四脯氨酸手性固定相（CSP）。将这两种溶液相合成的四脯氨酸CSP与通过逐步固相合成制备的CSP的色谱行为进行比较，结果表明，这三种溶液均具有相似的色谱性能，可分离53种模型分析物。这表明寡聚脯氨酸的溶液相合成具有良好的批次重现性，选择器均质性以及可能的低成本等特定优势，是寡聚脯氨酸CSP固相合成的可行替代方法。手性，2012年。©2012 Wiley Periodicals，Inc.。
• Highly Enantioseletive Biginelli Reaction Using a New Chiral Ytterbium Catalyst:  Asymmetric Synthesis of Dihydropyrimidines
  作者：Yijun Huang、Fengyue Yang、Chengjian Zhu

  DOI：10.1021/ja056092f

  日期：2005.11.30

  enantioselective three-component Biginelli condensation catalyzed by a recyclable chiral ytterbium triflate with a novel hexadentate amine phenol ligand containing a pyridyl group has been developed. A wide range of optically active dihydropyrimidines with remarkable pharmacological interest was obtained in high yields with good to excellent enantioselectivities under mild conditions.

  已开发出由可回收的手性三氟甲磺酸镱与含有吡啶基的新型六齿胺苯酚配体催化的高对映选择性三组分 Biginelli 缩合反应。在温和条件下以高产率获得了具有显着药理学意义的多种旋光二氢嘧啶，具有良好到优异的对映选择性。
• Combined Role of the Asymmetric Counteranion-Directed Catalysis (ACDC) and Ionic Liquid Effect for the Enantioselective Biginelli Multicomponent Reaction
  作者：Haline G. O. Alvim、Danielle L. J. Pinheiro、Valter H. Carvalho-Silva、Mariana Fioramonte、Fabio C. Gozzo、Wender A. da Silva、Giovanni W. Amarante、Brenno A. D. Neto

  DOI：10.1021/acs.joc.8b02101

  日期：2018.10.5

  This work describes new chiral task-specific ionic liquids bearing chiral anions as the catalysts for the enantioselective multicomponent Biginelli reaction. For the first time, the combined role of asymmetric counteranion-directed catalysis (ACDC) and ionic liquid effect (ILE) for the chiral induction in the Biginelli multicomponent reaction is demonstrated. The chiral induction arises from a supramolecular

  这项工作描述了带有手性阴离子的新型手性任务专用离子液体，作为对映选择性多组分Biginelli反应的催化剂。首次证明了在Biginelli多组分反应中，不对称抗衡阴离子导向催化（ACDC）和离子液体效应（ILE）在手性诱导中的结合作用。手性诱导来自超分子聚集体，其中催化剂的阴离子和阳离子与反应的关键阳离子中间体一起。新催化剂的每个成分对于成功的手性诱导都起着至关重要的作用。此外，首次使用电喷雾（串联）质谱法ESI-MS（/ MS）证明了这种多组分反应的不对称形式的机理。分析表明该反应优先且仅通过亚胺机理发生。通过ESI-MS检测到前所未有的超分子聚集体，并通过ESI-MS / MS对其进行了表征。其他两个可能的反应途径的中间没有被检测到。理论计算揭示了手性诱导关键步骤中转化的过渡状态，并有助于阐明手性阴离子（ACDC的贡献）和含咪唑鎓的非手性阳离子衍生物（ILE的贡献）在分子反应中的作用过程。
• Crystal Structure of Ethyl (2Z, 5R)-2-benzylidene-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-[1,3] Thiazolo [3,2-a] Pyrimidine-6-carboxylate
  作者：Mukesh M. Jotani、Bharat B. Baldaniya、Jerry P. Jasinski

  DOI：10.1007/s10870-009-9587-z

  日期：2009.12

  The title compound, C23H20N2O3S, (I), crystallizes in the orthorhombic space group, Pna 2 1 , with cell parameters a = 18.7975(6), b = 12.5173(4), c = 8.4804(3) Å, Z = 4. The molecular structure consists of a central pyrimidine ring which is significantly puckered to assume a screw-boat conformation fused to a thiazole ring with benzyl, carboxylate, methyl, phenyl and oxy groups bonded around this fused-ring moiety. The dihedral angle between the mean planes of the thiazole, benzyl and phenyl groups and the mean plane of the pyrimidine ring is 6.1(4)°, 83.8(7)° and 6.8(4)°, respectively. The dihedral angle between the mean planes of the benzyl and phenyl rings is 88.3(5)° while between the mean planes of the phenyl and thiazole groups measures 12.6(6)°. In the absence of expected hydrogen bonding interactions, the crystal packing is influenced by a collective action of strong intramolecular C–H···S hydrogen bond interactions, close C–H···O intramolecular contacts and O–Cg π-ring interactions. A DFT molecular orbital calculation gives support to these observations. Crystal Structure of Ethyl (2Z, 5R)-2-benzylidene-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-[1,3] thiazolo [3,2-a] pyrimidine-6-carboxylate is reported and its geometric parameters described. In the absence of expected hydrogen bonding interactions, the crystal packing is influenced by strong intramolecular C–H···S hydrogen bond interactions, close C–H···O intramolecular contacts and O–Cg π-ring interactions. A DFT molecular orbital calculation gives support to these observations.

  。
• Synthesis of a novel sterically hindered chiral cyclic phosphoric acid derived from l-tartaric acid and application to the asymmetric catalytic Biginelli reaction
  作者：Xiaoyun Hu、Rui Zhang、Jinsheng Xie、Zhongqiang Zhou、Zixing Shan

  DOI：10.1016/j.tetasy.2016.11.014

  日期：2017.1

  A novel sterically hindered chiral cyclic phosphoric acid derived from L-tartaric acid was designed and synthesized based on highly regioselective cyclosulfitation of chiral 1,1,4,4-tetraphenylbutanetetraol. The asymmetric Biginelli reaction catalyzed by this newly synthesized chiral phosphoric acid was examined, and enantioselectivities up to 99% ee was obtained. (C) 2016 Elsevier Ltd. All rights reserved.