4-(2,3-二氯苯基)-6-甲基-2-氧代-1,2,3,4-四氢嘧啶-5-羧酸乙酯 | 112080-30-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 4-(2,3-二氯苯基)-6-甲基-2-氧代-1,2,3,4-四氢嘧啶-5-羧酸乙酯
• 英文名称: Ethyl 4-(2,3-dichlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: ethyl 4-(2,3-dichlorophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 112080-30-5
• 化学式: C₁₄H₁₄Cl₂N₂O₃
• 分子量: 329.183
• InChiKey: LCJXNRFZPHKEMQ-UHFFFAOYSA-N

物化性质

• 熔点：
  215-216 °C(Solv: ethanol (64-17-5))
• 沸点：
  423.4±45.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：
  3

反应信息

• 作为反应物：
  描述：

  4-(2,3-二氯苯基)-6-甲基-2-氧代-1,2,3,4-四氢嘧啶-5-羧酸乙酯 在 chiral silica-based resin 、 溶剂黄146 作用下， 以 正己烷 、 异丙醇 为溶剂， 生成 ethyl (4S)-4-(2,3-dichlorophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate 、 ethyl (4R)-4-(2,3-dichlorophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
  参考文献：
  名称：

  The enantiomeric recognition of dihydropyrimidonic compounds by chiral selectors derived from 4- or 2-chloro-3,5-dinitrobenzoic acid

  摘要：

  Six new chiral packing materials for high performance liquid chromatography have been prepared from chiral selectors consisting of 4- or 2-chloro-3,5-dinitrobenzoic acid, L-alanine and different pi-donor aromatic units. Comparative tests of these newly prepared CSPs on separation efficiency for 13 racemic dihydropyrimidonic (DHPM) analytes have revealed the strong contribution of the pi-acceptor branching unit, as well as the important influence of the structure of the terminal pi-donor unit. The role of the terminal aromatic group is primarily to increase the rigidity of the selector structure. Comparisons of the data revealed that selectors bound on the silica gel could be preorganized during the process of chiral recognition, resulting in the similar enantioseparation properties for DHPM analytes on both types of CSPs. However, some other compounds, such as amino alcohol beta-agonists, exhibit very different enantioseparations. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.042
• 作为产物：
  描述：

  2-[(2,3-二氯苯基)亚甲基]-3-氧代丁酸乙酯 在 盐酸 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(2,3-二氯苯基)-6-甲基-2-氧代-1,2,3,4-四氢嘧啶-5-羧酸乙酯
  参考文献：
  名称：

  O'Reilly, Brian C.; Atwal, Karnail S., Heterocycles, 1987, vol. 26, # 5, p. 1185 - 1188

  摘要：

  DOI：

文献信息

• Polyphosphate Ester-Mediated Synthesis of Dihydropyrimidines. Improved Conditions for the Biginelli Reaction
  作者：C. Oliver Kappe、S. Fabio Falsone

  DOI：10.1055/s-1998-1764

  日期：1998.7

  Dihydropyrimidines 7 are prepared in high yield by a one-pot condensation of aldehydes, acetoacetates, and ureas using a polyphosphate ester-mediated cyclocondensation reaction. Yields are significantly higher than utilizing classical Biginelli reaction conditions.

  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。
• The Biginelli Condensation: A Novel and Efficient Regioselective Synthesis of Dihydropyrimidin-2(1<i>H</i>)-ones Using Lithium Bromide
  作者：Partha P. Baruah、Sunil Gadhwal、Dipak Prajapati、Jagir S. Sandhu

  DOI：10.1246/cl.2002.1038

  日期：2002.10

  Various substituted 3,4-dihydropyrimidin-2(1H)-ones were synthesised in one-pot reaction of aldehydes, β-ketoesters and urea using LiBr in tetrahydrofuran in excellent yields without any side reactions as observed by Biginelli and others.

  多种取代的3,4-二氢嘧啶-2(1H)-酮通过醛、β-酮酯和尿素的一锅反应合成，使用LiBr在四氢呋喃中反应，产率极佳且未观察到任何副反应，正如Biginelli等人所报告的。
• Potential antitumoral 3,4-dihydropyrimidin-2-(1H)-ones: synthesis, in vitro biological evaluation and QSAR studies
  作者：Mariana Matias、Gonçalo Campos、Adriana O. Santos、Amílcar Falcão、Samuel Silvestre、Gilberto Alves

  DOI：10.1039/c6ra14596e

  日期：——

  The search for novel anticancer agents with higher selectivity and lower toxicity remains a medical need.

  寻找具有更高选择性和更低毒性的新型抗癌药物仍然是医学上的需求。
• Highly versatile solid phase synthesis of biofunctional 4-aryl-3,4-dihydropyrimidines using resin-bound isothiourea building blocks and multidirectional resin cleavage
  作者：C.Oliver Kappe

  DOI：10.1016/s0960-894x(99)00572-7

  日期：2000.1

  A series of pharmacologically active, functionalized 4-aryl-3,4-dihydropyrimidine-5-carboxylates (DHPMs) are prepared by a versatile novel solid phase approach. In the key step, a polymer-bound thiouronium salt is condensed with unsaturated beta-ketoesters. The resulting polymer bound 1,4-dihydropyrimidines are cleaved from the resin employing multidirectional resin cleavage strategies. (C) 1999 Elsevier Science Ltd. All rights reserved.
• 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