ethyl 1-formyl-1,2,3,6-tetrahydro-4-methyl-2-oxo-6-phenyl-pyrimidin-5-carboxylate | 123044-14-4

• 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-formyl-1,2,3,6-tetrahydro-4-methyl-2-oxo-6-phenyl-pyrimidin-5-carboxylate
• 英文别名: ethyl 1-formyl-4-methyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate；5-ethoxycarbonyl-6-methyl-3-formyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one；Ethyl 3-formyl-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate；ethyl 3-formyl-6-methyl-2-oxo-4-phenyl-1,4-dihydropyrimidine-5-carboxylate
• CAS: 123044-14-4
• 化学式: C₁₅H₁₆N₂O₄
• 分子量: 288.303
• InChiKey: OCDYWBIASPWQFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 1-formyl-1,2,3,6-tetrahydro-4-methyl-2-oxo-6-phenyl-pyrimidin-5-carboxylate 生成 (S)-3-Formyl-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester
  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
• 作为产物：
  描述：

  2-(2-乙氧基羰基乙基)硫代-6-甲基-4-苯基-1,4-二氢嘧啶-5-羧酸乙酯 在 三氯氧磷 作用下， 反应 1.0h， 生成 ethyl 1-formyl-1,2,3,6-tetrahydro-4-methyl-2-oxo-6-phenyl-pyrimidin-5-carboxylate
  参考文献：
  名称：

  Kappe, Christian Oliver; Roschger, Peter, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 55 - 64

  摘要：

  DOI：

文献信息

• A mild and practical method for the regioselective synthesis of N-acylated 3,4-dihydropyrimidin-2-ones. New acyl transfer reagents
  作者：Kamaljit Singh、Sukhdeep Singh

  DOI：10.1016/j.tetlet.2006.09.039

  日期：2006.11

  The treatment of 3,4-dihydropyrimidin-2-ones with n-BuLi at −78 °C, followed by quenching with various electrophiles furnished N3-substituted derivatives, regioselectively. Further, N1,N3-diacyl derivatives were found to transfer N1-acyl groups to nucleophilic sites.

  在-78°C下用正丁基锂处理3,4-二氢嘧啶-2-酮，然后用区域选择性选择性提供的N 3取代衍生物的各种亲电试剂淬灭。此外，发现N 1，N 3-二酰基衍生物将N 1-酰基转移至亲核位点。
• Metalation of Biginelli Compounds. A General Unprecedented Route to C-6 Functionalized 4-Aryl-3,4-dihydropyrimidinones
  作者：Kamaljit Singh、Sukhdeep Singh、Aman Mahajan

  DOI：10.1021/jo050675q

  日期：2005.7.1

  4-Aryl-6-methyl-3,4-dihydro-2(1H)-pyrimidinone esters (DHPMs) readily undergo metalation at the C-6 methyl (vinylogous ester) position on treatment with lithium diisopropylamide at −10 °C. The resulting anion intermediates can be treated with electrophilic reagents to afford functionalized DHPMs that have been chemically elaborated mainly at the C-6 position. Di- and trianion formation is also possible

  在-10°C下用二异丙基氨基锂处理时，4-芳基-6-甲基-3,4-二氢-2（1 H）-嘧啶酮酯（DHPM）易于在C-6甲基（乙烯基酯）位置发生金属化。可以用亲电试剂处理所得的阴离子中间体，以提供功能化的DHPM，该功能化的DHPM主要在C-6位置进行了化学修饰。当用过量当量的碱进行反应时，在乙烯基的甲基和NH位置也可能形成二阴离子和三阴离子。
• Synthesis and Reactions of Some Pyrimidine Derivatives
  作者：A. Mobinikhaledi、N. Foroughifar、T. Mosleh

  DOI：10.1080/10426500701752903

  日期：2008.6.9

  N-formylated thioxopyrimidines 3a-d, thiazine derivatives 4a–c and N-formylated oxopyrimidines 5a–d were synthesized by reaction of an appropriate ethyl 6-methyl-4-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate with DMF in the presence of POCl3 under different conditions. Furtherer reaction of the thiazine derivatives 4a–c with aqueous HCl under heating followed by neutralization with NaOH gave 7a–c

  通过适当的乙基 6-甲基-4-芳基-2-硫代-1,2 的反应合成了三个不同系列的化合物，包括 N-甲酰化的 thioxopyrimidines 3a-d、噻嗪衍生物 4a-c 和 N-甲酰化的 oxopyrimidines 5a-d ,3,4-tetrahydropyrimidine-5-carboxylate 与 DMF 在 POCl3 存在下在不同条件下。噻嗪衍生物 4a-c 在加热下与 HCl 水溶液进一步反应，然后用 NaOH 中和得到 7a-c。红外和核磁共振光谱以及元素分析用于鉴定新化合物。
• QSAR analysis of 2-oxo-1,2,3,4-tetrahydropyrimidine analogues of antibacterials
  作者：Ramesh L. Sawant、Manish S. Bhatia

  DOI：10.1135/cccc2009054

  日期：——

  QSAR analysis of two sets of analogues of 2-oxo-1,2,3,4-tetrahydropyrimidine was performed to investigate the relationship between their physicochemical parameters and antibacterial activity. Predictive and statistically significant models were generated. On the basis of these models new compounds were synthesized, structurally characterized and evaluated for their antibacterial potential. The potential of newly synthesized compounds was higher than the training set of compounds, in close agreement with QSAR prediction.

  对两组2-氧代-1,2,3,4-四氢嘧啶类似物进行QSAR分析，以研究它们的理化参数与抗菌活性之间的关系。生成了具有预测性和统计显著性的模型。基于这些模型，合成了新化合物，进行了结构表征，并评估了它们的抗菌潜力。新合成化合物的潜力高于训练集中的化合物，与QSAR预测结果密切一致。
• Metal-organic framework Cu3 (BTC)2(H2O)3 catalyzed Aldol synthesis of pyrimidine-chalcone hybrids
  作者：Naziyanaz B. Pathan、Anjali M. Rahatgaonkar、Mukund S. Chorghade

  DOI：10.1016/j.catcom.2011.03.040

  日期：2011.7

  A typical metal organic framework, [Cu3 (BTC)2(H2O)3, BTC = 1,3,5-benzene tricarboxylate] has been used for the synthesis of pyrimidine-chalcones. We have explored a green synthesis of pyrimidine chalcones under Cu3(BTC)2 catalysis by Aldol condensation. Easy isolation of product, excellent yield, and recyclable catalyst makes this reaction eco-friendly. The technology was demonstrated to be applicable

  典型的金属有机骨架[Cu 3（BTC）2（H 2 O）3，BTC = 1,3,5-苯三羧酸酯]已用于合成嘧啶-查耳酮。我们已经探索了通过Aldol缩合在Cu 3（BTC）2催化下的嘧啶查耳酮的绿色合成。易于分离产物，优异的收率和可回收的催化剂使该反应变得环保。事实证明，该技术适用于多种化学杂化物的合成。