ethyl 1,2,3,4-tetrahydro-1,4,6-trimethyl-2-oxopyrimidine-5-carboxylate | 14757-93-8

• 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 1,2,3,4-tetrahydro-1,4,6-trimethyl-2-oxopyrimidine-5-carboxylate
• 英文别名: ethyl 1,4,6-trimethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；1,4,6-trimethyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester；2-Oxo-5-ethoxycarbonyl-1,4,6-trimethyl-1.2.3.4-tetrahydro-pyrimidin；Ethyl 3,4,6-trimethyl-2-oxo-1,6-dihydropyrimidine-5-carboxylate
• CAS: 14757-93-8
• 化学式: C₁₀H₁₆N₂O₃
• 分子量: 212.249
• InChiKey: LREYCCLKUDUNFM-UHFFFAOYSA-N

物化性质

• 熔点：
  138 °C
• 沸点：
  368.1±42.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 1,2,3,4-tetrahydro-1,4,6-trimethyl-2-oxopyrimidine-5-carboxylate 、 氢氧化钾 生成 1,4,6-trimethyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid
  参考文献：
  名称：

  ZIGEUNER G.; KNOPP C.; BLASCHKE H., MONATSH. CHEM. , 1976, 107, NO 3, 587-603

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 1,2,3,4-tetrahydro-1,6-dimethyl-2-oxopyrimidine-5-carboxylate 在 硝酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 ethyl 1,2,3,4-tetrahydro-1,4,6-trimethyl-2-oxopyrimidine-5-carboxylate
  参考文献：
  名称：

  A highly regio- and chemoselective addition of carbon nucleophiles to pyrimidinones. A new route to C4 elaborated Biginelli compounds

  摘要：

  Ethyl 6-methyl-pyrimidine-2-one-5-carboxylates react with C-nucleophiles in a diversity oriented synthetic sequence to afford C4 substituted congeners of medicinally potent Biginelli dihydropyrimidinones, in a highly regioselective manner. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.12.111

文献信息

• Selective N1-Alkylation of 3,4-Dihydropyrimidin-2(1<i>H</i>)-ones Using Mitsunobu-Type Conditions
  作者：C. Oliver Kappe、Doris Dallinger

  DOI：10.1055/s-2002-34881

  日期：——

  The regioselective N1-alkylation of 3,4-dihydropyrimidin-2(1H)-ones via Mitsunobu reaction is reported. Using the highly reactive Mitsunobu coupling reagent combination N,N,N′,N′-tetramethylazodicarboxamide/tributylphosphine (TMAD-TBP) and a set of primary alcohols a small library of N1-alkylated dihydropyrimidones is obtained in good to excellent yields.

  报道了通过 Mitsunobu 反应实现 3,4-二氢嘧啶-2(1H)-酮的 N1-烷基选择性烷基化。使用高活性的 Mitsunobu 偶联试剂组合 N,N,N',N'-四甲基偶氮二羧酰胺/三丁基膦（TMAD-TBP）以及一系列伯醇，获得了产率良好至优异的一系列 N1-烷基化二氢嘧啶酮的小型化合物库。
• (C₅H₆N₄O)(C₅H₅N₄O)₃(C₅H₄N₄O)[Bi₂Cl₁₁]Cl₂as a simple and efficient catalyst in Biginelli reaction
  作者：Xiang Zhang、Xiaoyu Gu、Yuhua Gao、Shipeng Nie、Hongfei Lu

  DOI：10.1002/aoc.3590

  日期：2017.4

  A highly efficient and facile procedure for the one‐pot three‐component synthesis of 3,4‐dihydropyrimidin‐2‐(1H)ones/thiones from the one‐pot condensation of aldehyde, β‐dicarbonyl compound and urea/thiourea was developed. The methodology is applicable to a wide range of substrates with high yield in the presence of (C5H6N4O)(C5H5N4O)3(C5H4N4O)[Bi2Cl11]Cl2. The complex is an air‐stable, environmentally

  开发了一种高效，简便的方法，该方法可通过醛，β-二羰基化合物和尿素/硫脲的一锅缩合反应一锅三组分合成3,4-二氢嘧啶-2-（1 H）酮/硫酮。该方法适用于（C 5 H 6 N 4 O）（C 5 H 5 N 4 O）3（C 5 H 4 N 4 O）[Bi 2 Cl 11 ] Cl 2。该络合物是一种对空气稳定，对环境友好且可回收的催化剂，可以有效催化Biginelli反应。该催化剂具有高催化效率和低催化剂载量，并且可以循环十次而活性损失很小。
• An Efficacious Protocol for 4-Substituted 3,4-Dihydropyrimidinones: Synthesis and Calcium Channel Binding Studies
  作者：Kamaljit Singh、Divya Arora、Danielle Falkowski、Qingxin Liu、Robert S. Moreland

  DOI：10.1002/ejoc.200900208

  日期：2009.7

  anion of enantiopure chiral auxiliary (1R,2S,5R)-(-)-methyl (S)-p-toluenesulfinate to afford C-4 substituted and enantiopure congeners of medicinally potent Biginelli dihydropyrimidinones. The calcium channel blocking activity of some of the compounds was evaluated and compared with nifedipine for their ability to relax a membrane depolarization induced contraction.

  1,2-二氢-1,6-二甲基/ 6-甲基-2-氧嘧啶-5-羧酸乙酯与C-亲核试剂以及对映纯手性助剂（1R，2S，5R）-（-）-甲基的阴离子反应（S）-对甲苯磺酸盐，可得到具有药效的比吉内利二氢嘧啶酮的C-4取代对映体和对映体纯同系物。对某些化合物的钙通道阻断活性进行了评估，并与硝苯地平比较了它们舒张膜去极化引起的收缩的能力。
• A highly regio- and chemoselective addition of carbon nucleophiles to pyrimidinones. A new route to C4 elaborated Biginelli compounds
  作者：Kamaljit Singh、Divya Arora、Sukhdeep Singh

  DOI：10.1016/j.tetlet.2006.12.111

  日期：2007.2

  Ethyl 6-methyl-pyrimidine-2-one-5-carboxylates react with C-nucleophiles in a diversity oriented synthetic sequence to afford C4 substituted congeners of medicinally potent Biginelli dihydropyrimidinones, in a highly regioselective manner. (c) 2006 Elsevier Ltd. All rights reserved.
• ZIGEUNER G.; KNOPP C.; BLASCHKE H., MONATSH. CHEM. <MOCH-AP>, 1976, 107, NO 3, 587-603
  作者：ZIGEUNER G.、 KNOPP C.、 BLASCHKE H.

  DOI：——

  日期：——