5-benzoyl-4,6-diphenyl-1,2,3,4-tetrahydro-2-thioxopyrimidine | 253328-49-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 5-benzoyl-4,6-diphenyl-1,2,3,4-tetrahydro-2-thioxopyrimidine
• 英文别名: (4,6-diphenyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidin-5-yl)-phenylmethanone
• CAS: 253328-49-3
• 化学式: C₂₃H₁₈N₂OS
• 分子量: 370.475
• InChiKey: XHTPYFWSSVJNKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  73.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-benzoyl-4,6-diphenyl-1,2,3,4-tetrahydro-2-thioxopyrimidine 以 甲醇 为溶剂， 反应 3.17h， 生成 3-acetyl-5-benzoyl-4,6-diphenyl-4H-2-methylthioxopyrimidine
  参考文献：
  名称：

  Studies on Reactions of Pyrimidine Compounds: Synthesis and Reactions of 5-Benzoyl-4,6-Diphenyl-1,2,3,4-Tetrahydro-2-Thioxopyrimidine

  摘要：

  The 5-benzoyl-4,6-diphenyl-1,2,3,4-tetrahydro-2-thioxopyrimidin (1) have been prepared via Biginelli cyclocondensation reaction in acetic acid under reflux condition in good yield (93%). Reactions of 1 and iodomethane to afford thiopyrimidine compounds 3 and 5. Also, the acetylation of compounds 1 and 3 gave 3-acetyl thioxopyrimidine 2 and methylthiopyrimidine 4, respectively. Thioxopyrimidine derivative 6 was synthesized from 1 and POCl3/DMF Furthermore, the starting compound 1 were cyclized with various bromo compounds to the thiazolopyrimidine 7, 8, 9 and pyrimido[2,3-b]thiazine10 derivatives, in approximately 55-78% yields. The purpose of synthesizing the thioxopyrimidine derivatives is because of the high biological activities. All of these derivatives have been characterized by analytical and spectroscopic studies and the reaction mechanism is discussed.

  DOI：

  10.1080/10426500701263554
• 作为产物：
  描述：

  苯甲醛 、 二苯甲酰基甲烷 、 硫脲 在 盐酸 、 溶剂黄146 作用下， 反应 0.08h， 以75%的产率得到5-benzoyl-4,6-diphenyl-1,2,3,4-tetrahydro-2-thioxopyrimidine
  参考文献：
  名称：

  嘧啶化合物反应的研究。21. 1,2,3,4-Tetrahydro-2-Thioxopyrimidine 衍生物的微波辅助合成

  摘要：

  5-苯甲酰基-4,6-二苯基-1,2,3,4-四氢-2-硫代嘧啶 (1a) 和 5-苯甲酰基-4-(2-氯苯基)-6-苯基-1,2,3,在微波辐射下，使用 β-二酮、芳醛和硫脲的 Biginelli 三组分环缩合反应合成了 4-四氢-2-硫代嘧啶 (1b)。通过起始化合物1b与2-溴丙酸、溴乙酸和3-溴丙酸的简单一锅缩合反应得到噻唑并嘧啶(2)、(3)和嘧啶并[2,3-b]噻嗪(4)衍生物，分别。这些反应在微波辐射和常规条件下进行。该研究提出了一种简单有效的制备 1,2,3,4-四氢-2-硫代嘧啶及其衍生物的途径。

  DOI：

  10.1080/10426500701557021

文献信息

• Theoretical calculation of newly synthesized tetrazolopyrimidine derivatives as a potential corrosion inhibitor
  作者：Erdem Ergan、Nurullah Seker、Begum Akbas、Esvet Akbas

  DOI：10.2298/jsc210419067g

  日期：——

  In this work, we wanted to define a general and comprehensive strategy for the synthesis of tetrazolo[1,5-a]pyrimidine derivatives. For this purpose, we obtained new tetrazolo[1,5-a]pyrimidine molecules via the mercurypromoted desulfurization reaction, including hydrolysis, cyclizations, and eliminations. All of the molecules were characterized by FT-IR, 1H-NMR, 13C- -NMR, and elemental analysis. On the other hand, the potentials of compounds as corrosion inhibitors were calculated at B3LYP/6-31G (d, p) level via density functional theory (DFT).

  在这项工作中，我们希望为四唑并[1,5-a]嘧啶衍生物的合成确定一种通用而全面的策略。为此，我们通过汞促进的脱硫反应，包括水解、环化和消去反应，获得了新的四唑并[1,5-a]嘧啶分子。所有分子都通过傅立叶变换红外光谱、1H-核磁共振、13C-核磁共振和元素分析进行了表征。另一方面，通过密度泛函理论（DFT）在 B3LYP/6-31G (d, p) 水平上计算了化合物作为缓蚀剂的潜力。
• Studies on Reactions of Pyrimidine Compounds: Synthesis and Reactions of 5-Benzoyl-4,6-Diphenyl-1,2,3,4-Tetrahydro-2-Thioxopyrimidine
  作者：Furgan Aslanoğlu、Esvet Akbaş、Mehmet Sönmez、Barış Anıl

  DOI：10.1080/10426500701263554

  日期：2007.6.1

  The 5-benzoyl-4,6-diphenyl-1,2,3,4-tetrahydro-2-thioxopyrimidin (1) have been prepared via Biginelli cyclocondensation reaction in acetic acid under reflux condition in good yield (93%). Reactions of 1 and iodomethane to afford thiopyrimidine compounds 3 and 5. Also, the acetylation of compounds 1 and 3 gave 3-acetyl thioxopyrimidine 2 and methylthiopyrimidine 4, respectively. Thioxopyrimidine derivative 6 was synthesized from 1 and POCl3/DMF Furthermore, the starting compound 1 were cyclized with various bromo compounds to the thiazolopyrimidine 7, 8, 9 and pyrimido[2,3-b]thiazine10 derivatives, in approximately 55-78% yields. The purpose of synthesizing the thioxopyrimidine derivatives is because of the high biological activities. All of these derivatives have been characterized by analytical and spectroscopic studies and the reaction mechanism is discussed.
• Studies on Reactions of Pyrimidine Compounds. 2¹. Microwave-Assisted Synthesis of 1,2,3,4-Tetrahydro-2- Thioxopyrimidine Derivatives
  作者：Esvet Akbaş、Furgan Aslanoğlu

  DOI：10.1080/10426500701557021

  日期：2007.12.24

  cyclocondensation reaction of a β -diketone, arylaldehyde, and thiourea under microwave irradiation. Thiazolopyrimidine ( 2 ), ( 3 ) and pyrimido[2,3-b]thiazine ( 4 ) derivatives were obtained by a simple one-pot condensation reaction of starting compound 1b and 2-bromopropionic acid, bromoacetic acid and 3-bromopropionic acid, respectively. These reactions performed under microwave irradiation and conventional

  5-苯甲酰基-4,6-二苯基-1,2,3,4-四氢-2-硫代嘧啶 (1a) 和 5-苯甲酰基-4-(2-氯苯基)-6-苯基-1,2,3,在微波辐射下，使用 β-二酮、芳醛和硫脲的 Biginelli 三组分环缩合反应合成了 4-四氢-2-硫代嘧啶 (1b)。通过起始化合物1b与2-溴丙酸、溴乙酸和3-溴丙酸的简单一锅缩合反应得到噻唑并嘧啶(2)、(3)和嘧啶并[2,3-b]噻嗪(4)衍生物，分别。这些反应在微波辐射和常规条件下进行。该研究提出了一种简单有效的制备 1,2,3,4-四氢-2-硫代嘧啶及其衍生物的途径。