5-benzoyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-thione

• 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: 5-benzoyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-thione
• 英文别名: 5-benzoyl-6-methyl-4-phenyl-1,2,3,4-tetrahydropyrimidine-2-thione；(6-methyl-4-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenylmethanone；4-Methyl-5-benzoyl-6-phenyl-3,6-dihydropyrimidine-2(1H)-thione；(6-methyl-4-phenyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidin-5-yl)-phenylmethanone
• 化学式: C₁₈H₁₆N₂OS
• 分子量: 308.404
• InChiKey: BDBZXKWADBGAHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-thione 在 劳森试剂 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 16.5h， 生成 (2E)-7-methyl-2-[7-methyl-3-oxo-5-phenyl-6-(phenylcarbonyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-2(3H)-ylidene]-5-phenyl-6-(phenylcarbonyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-3(2H)-one
  参考文献：
  名称：

  Oxidation of thiazolo[3,2-a]pyrimidin-3(2H)-ones with DMSO and Lawesson’s reagent

  摘要：

  2,2'-Dimers with a central double bond were prepared by the oxidation of 5,6-disubstituted 7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-3(2H)-ones with DMSO and Lawesson's reagent at room temperature. The role of DMSO as an oxidizing reagent was confirmed by NMR spectroscopy. The E-configuration of the central C=C bond for the two diastereomers of compound 8m was proven by single crystal X-ray data. The dimeric thiazolopyrimidines were orange or red colored and absorption bands at 283-330 and 459-476 nm were observed in the UV spectra. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2018.02.014
• 作为产物：
  描述：

  苯甲醛 、 硫脲 、 1-苯基-1,3-丁二酮 在 sulfated zirconia 作用下， 反应 0.03h， 以93%的产率得到5-benzoyl-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-thione
  参考文献：
  名称：

  微波辐射下硫酸化氧化锆催化一锅法良性合成 3,4-二氢嘧啶-2(1H)-酮

  摘要：

  硫酸化氧化锆已被证明是在微波辐射和常规加热下合成 3,4-二氢嘧啶-2(1H)-酮的有效催化剂。固体酸催化剂...

  DOI：

  10.1246/cl.2006.1074

文献信息

• Nitrosation of 5H-thiazolo[3,2-a]pyrimidin-3(2H)-ones
  作者：Evgenia A. Lashmanova、Andrey K. Shiryaev

  DOI：10.1007/s10593-015-1710-9

  日期：2015.4

  The reaction of 2,3-dihydro-5H-thiazolo[3,2-a]pyrimidin-3-ones with sodium nitrite in acetic acid at room temperature gave 2-(hydroxyimino)-5Н-thiazolo[3,2-a]pyrimidin-3(2Н)-ones, which exist as a single isomer according to NMR data. Calculations by the B3LYP/6-311++G(d,p) method indicated that the Е-isomer of hydroxyimino derivative was favored by 15.7 kJ/mol over the Z-isomer.

  室温下，2,3-二氢-5 H-噻唑并[3,2 - a ]嘧啶-3-酮与亚硝酸钠在乙酸中的反应得到2-（羟基亚氨基）-5Н-噻唑并[3,2-一个]嘧啶3（2 Н） -酮，根据NMR数据，其作为单一异构体。通过B3LYP / 6-311 ++ G（d，p）方法进行的计算表明，羟基亚氨基衍生物的Å-异构体比Z-异构体的亲和力高15.7 kJ / mol 。
• A Practical and Green Approach towards Synthesis of Dihydropyrimidinones without Any Solvent or Catalyst
  作者：Brindaban C. Ranu、Alakananda Hajra、Suvendu S. Dey

  DOI：10.1021/op0255478

  日期：2002.11.1

  A simple, efficient, green, and cost-effective procedure has been developed for the synthesis of dihydropyrimidinones by a solvent-free and catalyst-free Biginelli's condensation of 1,3-dicarbonyl compound, aldehyde, and urea. This approach of direct reaction in neat without solvent and catalyst shows a new direction in green synthesis.

  已经开发了一种简单、高效、绿色和经济有效的方法，用于通过 1,3-二羰基化合物、醛和尿素的无溶剂和无催化剂 Biginelli 缩合合成二氢嘧啶酮。这种无溶剂、无催化剂直接反应的方法为绿色合成指明了新的方向。
• Synthesis of 5-Acyl-3,4-dihydropyrimidine-2-thiones via Solvent-Free, Solution-Phase and Solid-Phase Biginelli Procedures
  作者：Roman Lopez、Horacio Comas、David-Alexandre Buisson、Romain Najman、Frank Kozielski、Bernard Rousseau

  DOI：10.1055/s-0029-1217373

  日期：2009.7

  Compounds belonging to the 5-acyl-3,4-dihydropyrimidine-2-thione family were obtained using a solvent-free Biginelli condensation with or without the use of a catalyst. An unprecedented solid-phase procedure involving a polymer-supported aldehyde allowed the preparation of a series of 5-aroyl derivatives starting with crude diketones obtained from their corresponding aryl esters.

  在使用或不使用催化剂的情况下，通过无溶剂 Biginelli 缩合反应获得了属于 5-酰基-3,4-二氢嘧啶-2-硫酮家族的化合物。一种前所未有的固相程序涉及聚合物支撑的醛，该程序允许从相应芳基酯的粗二酮开始，制备一系列 5-芳酰基衍生物。
• Synthesis of 3,4‐Dihydropyrimidine‐2(1<i>H</i>)‐thiones and Quinazolin‐4(3<i>H</i>)‐ones over Yb(III)‐Resin Catalyst Under Solvent‐free Conditions
  作者：Zhidong Jiang、Ruifang Chen

  DOI：10.1081/scc-200049766

  日期：2005.3

  reagent supported on ion exchange resin is applied to the multicomponent condensation reactions under solvent‐free conditions. One‐pot synthesis of a library of 3,4‐dihydropyrimidine‐2(1H)‐thiones and quinazolin‐4(3H)‐ones were described. The advantages of easy separation and recyclability of the catalysts were demonstrated.

  摘要 载于离子交换树脂上的镱（III）试剂用于无溶剂条件下的多组分缩合反应。描述了 3,4-二氢嘧啶-2(1H)-硫酮和喹唑啉-4(3H)-酮库的一锅法合成。证明了催化剂易于分离和可回收的优点。
• Sulfated Zirconia-catalyzed One-pot Benign Synthesis of 3,4-Dihydropyrimidin-2(1<i>H</i>)-ones under Microwave Irradiation
  作者：Dalip Kumar、M. Swapna Sundaree、Braja Gopal Mishra

  DOI：10.1246/cl.2006.1074

  日期：2006.9

  Sulfated zirconia has been demonstrated as an efficient catalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones under microwave irradiation and conventional heating. The solid acid catalyst i...

  硫酸化氧化锆已被证明是在微波辐射和常规加热下合成 3,4-二氢嘧啶-2(1H)-酮的有效催化剂。固体酸催化剂...