ethyl 4-(4-chlorophenyl)-2-oxo-6-(tosylmethyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 902277-69-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 4-(4-chlorophenyl)-2-oxo-6-(tosylmethyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: Ethyl 4-(4-chlorophenyl)-6-[(4-methylbenzenesulfonyl)methyl]-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；ethyl 4-(4-chlorophenyl)-6-[(4-methylphenyl)sulfonylmethyl]-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 902277-69-4
• 化学式: C₂₁H₂₁ClN₂O₅S
• 分子量: 448.927
• InChiKey: AUQAFBBTGOFZHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl-6-(bromomethyl)-4-(4-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 、 sodium 4-methylbenzenesulfinate 在 PEG-400 作用下， 以 水 为溶剂， 反应 24.0h， 以92%的产率得到ethyl 4-(4-chlorophenyl)-2-oxo-6-(tosylmethyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  General and Green Synthesis of C-6 Sulfonylmethyl 4-Aryl-3,4-dihydropyrimidinones in Water

  摘要：

  A simple, inexpensive, and green reaction permitting the synthesis of new C-6 arylsulfonylmethyl 4-aryl-3,4-dihydropyrimidinones in water by S-alkylation of 6-bromomethyl 3,4-dihydropyrimidinones 2 with benzenesulfinic acid anions 3 is reported. The required 6-bromomethyldihydropyrimidone precursors 2 were readily prepared using an organic solid brominating reagent.

  DOI：

  10.1080/00397910802654682

文献信息

• A microwave-mediated catalyst- and solvent-free regioselective Biginelli reaction in the synthesis of highly functionalized novel tetrahydropyrimidines
  作者：Palani Sokkan Harikrishnan、Stephen Michael Rajesh、Subbu Perumal、Abdulrahman I. Almansour

  DOI：10.1016/j.tetlet.2012.12.034

  日期：2013.2

  novel ethyl 2-oxo/thio-4-aryl-6-(arylsulfonylmethyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylates has been synthesized regioselectively by the Biginelli reaction of ethyl 3-oxo-4-(arylsulfonyl)butanoate, aromatic aldehyde and urea/thiourea under microwave irradiation and solvent- and catalyst-free conditions.

  通过3-氧代-4-乙基乙基的Biginelli反应选择性地合成了一系列新型的2-氧代/硫代-4-芳基-6-（芳基磺酰基甲基）-1,2,3,4-四氢嘧啶-5-羧酸乙酯。 （芳基磺酰基）丁酸酯，芳族醛和脲/硫脲在微波辐射下以及无溶剂和无催化剂的条件下。