ethyl 2,4-diphenyl-6-methyl-1,4-dihydropyrimidine-5-carboxylate | 100631-80-9

• 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 2,4-diphenyl-6-methyl-1,4-dihydropyrimidine-5-carboxylate
• 英文别名: ethyl 6-methyl-2,4-diphenyl-1,4-dihydropyrimidine-5-carboxylate
• CAS: 100631-80-9
• 化学式: C₂₀H₂₀N₂O₂
• 分子量: 320.391
• InChiKey: KTGTURCKUADLTP-UHFFFAOYSA-N

物化性质

• 熔点：
  106-108 °C
• 沸点：
  489.6±45.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2,4-diphenyl-6-methyl-1,4-dihydropyrimidine-5-carboxylate 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以63.8%的产率得到ethyl 4-methyl-2,6-diphenylpyrimidine-5-carboxylate
  参考文献：
  名称：

  Studies on Cerebral Protective Agents. I. Novel 4-Arylpyrimidine Derivatives with Anti-anoxic and Anti-lipid Peroxidation Activities.

  摘要：

  通过氧化4-芳基-1,4-二氢嘧啶合成了新型4-芳基嘧啶衍生物，并研究了它们对小鼠抗缺氧（AA）活性和大鼠线粒体抗脂质过氧化（ALP）活性的影响。在这些化合物中，乙基6-甲基-2-苯基-4-(4-吡啶基)-5-嘧啶羧酸酯（4b）具有AA活性（10mg/kg，腹腔注射），而乙基6-甲基-4-(3-硝基苯基)-2-苯基-5-嘧啶羧酸酯（4f）具有ALP活性（73%抑制在10μg/ml）。后者化合物（100mg/kg，腹腔注射）对大鼠花生四烯酸引起的脑水肿也有效，其效力与维生素E相当。

  DOI：

  10.1248/cpb.40.1452
• 作为产物：
  描述：

  (Z)-ethyl 2-benzylidenacetoacetate 在 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 48.5h， 生成 ethyl 2,4-diphenyl-6-methyl-1,4-dihydropyrimidine-5-carboxylate
  参考文献：
  名称：

  A Versatile Two-Step Synthesis of Dihydropyrimidines

  摘要：

  DOI：

  10.1055/s-1985-31263

文献信息

• Palladium(0)-Catalyzed, Copper(I)-Mediated Coupling of Boronic Acids with Cyclic Thioamides. Selective Carbon−Carbon Bond Formation for the Functionalization of Heterocycles^†
  作者：Hana Prokopcová、C. Oliver Kappe

  DOI：10.1021/jo070408f

  日期：2007.6.1

  Employing controlled microwave irradiation at 100 °C, most cross-couplings can be completed within 2 h and proceed in high yields. An advantage of using thioamides as starting materials is the fact that the system can be tuned to an alternative carbon−sulfur cross-coupling pathway by changing to stoichiometric copper(II) under oxidative conditions. Both types of thioamide cross-couplings are orthogonal to

  描述了在化学计量的铜（I）辅因子存在下，钯催化的环硫酰胺与芳基硼酸的交叉偶联。脱硫碳-碳交叉偶联方案是在中性条件下进行的，可应用于具有嵌入的硫酰胺片段的杂环结构。成功的碳-碳交叉偶联与环大小，芳香性/非芳香性，起始硫酰胺结构中是否存在其他杂原子或其他官能团无关。通过在100°C下控制微波辐射，大多数交叉偶联可在2 h内完成，并以高收率进行。使用硫代酰胺作为起始原料的一个优点是，可以通过在氧化条件下更改为化学计量的铜（II），将系统调节至另一种碳-硫交叉偶联途径。两种类型的硫酰胺交叉偶联均与芳烃卤化物与硼酸的传统碱催化的Suzuki-Miyaura交叉偶联正交。
• A domino desulfurative coupling–acylation–hydration–Michael addition process for the synthesis of polysubstituted tetrahydro-4H-pyrido[1,2-a]pyrimidines
  作者：Zhong-Fei Yan、Zheng-Jun Quan、Yu-Xia Da、Zhang Zhang、Xi-Cun Wang

  DOI：10.1039/c4cc05090h

  日期：——

  A novel method for the synthesis of the polysubstituted tetrahydro-4H-pyrido[1,2-a]pyrimidines through a domino desulfurative coupling–acylation–hydration and Michael addition sequence was established.

  建立了一种通过多米诺脱硫偶联-酰化-水合和迈克尔加成序列合成多取代四氢-4H-吡啶并[1,2-a]嘧啶的新方法。
• Tunable Carbon−Carbon and Carbon−Sulfur Cross-Coupling of Boronic Acids with 3,4-Dihydropyrimidine-2-thiones
  作者：Alenka Lengar、C. Oliver Kappe

  DOI：10.1021/ol036496h

  日期：2004.3.1

  Direct microwave-assisted Pd(0)-catalyzed/Cu(I)-mediated carbon-carbon cross-coupling of 3,4-dihydropyrimidine-2-thiones and boronic acids under Liebeskind-Srogl conditions leads to 2-aryl-1,4-dihydropyrimidines in moderate to high yield. In contrast, Cu(II)-mediated reaction of the same substrates leads to carbon-sulfur cross-coupling. [reaction: see text]

  Liebeskind-Srogl条件下3,4-二氢嘧啶-2-硫酮与硼酸的直接微波辅助Pd（0）催化/ Cu（I）介导的碳-碳交叉偶联导致2-芳基-1,4 -二氢嘧啶，中等至高产率。相反，相同底物的Cu（II）介导的反应导致碳-硫交叉偶联。[反应：看文字]
• Wool-anchored Pd(OAc)₂ complex: a highly active and reusable catalyst for desulfurative coupling reactions
  作者：Quanlu Yang、Zhengjun Quan、Baoxin Du、Shang Wu、Peidong Li、Yanxia Sun、Ziqiang Lei、Xicun Wang

  DOI：10.1039/c5cy00802f

  日期：——

  A biomacromolecule-anchored palladium complex, wool-Pd(OAc)₂, was used as a catalyst for the Liebeskind–Srogl desulfurative coupling reactions of pyrimidin-yl thioether derivatives with terminal alkynes and arylboronic acids.

  一种生物大分子锚定的钯配合物，羊毛-Pd(OAc)₂，被用作催化剂，用于Liebeskind–Srogl去硫偶联反应，将嘧啶基硫醚衍生物与末端炔烃和芳基硼酸进行偶联。
• Investigating the Existence of Nonthermal/Specific Microwave Effects Using Silicon Carbide Heating Elements as Power Modulators
  作者：Tahseen Razzaq、Jennifer M. Kremsner、C. Oliver Kappe

  DOI：10.1021/jo8009402

  日期：2008.8.1

  [GRAPHICS]The use of passive heating elements made out of chemically inert sintered silicon carbide (SiC) allows microwave transparent or poorly absorbing reaction mixtures to be heated under microwave conditions. The cylindrical heating inserts efficiently absorb microwave energy and subsequently transfer the generated thermal energy via conduction phenomena to the reaction mixture. In the case of low to medium microwave absorbing reaction mixtures, the addition of SiC heating elements results in significant reductions (30-70%) in the required microwave power as compared to experiments performed without heating element at the same temperature. The method has been used to probe the influence of microwave power (electromagnetic field strength) on chemical reactions. Six diverse types of chemical transformations were performed in the presence or absence of a SiC heating element at the same reaction temperature but at different microwave power levels. In all six cases, the measured conversions/yields were similar regardless of whether a heating element was used or not. The applied microwave power had no influence on the reaction rate, and only the attained temperature governed the outcome of a specific chemical process under microwave conditions.