5-(methoxycarbonyl)-6-methyl-4-(3-bromophenyl)-3,4-dihydropyrimidin-2(1H)-thione

• 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: 5-(methoxycarbonyl)-6-methyl-4-(3-bromophenyl)-3,4-dihydropyrimidin-2(1H)-thione
• 英文别名: methyl 4-(3-bromophenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₁₃H₁₃BrN₂O₂S
• 分子量: 341.228
• InChiKey: IWIBOCWOUBYAPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(methoxycarbonyl)-6-methyl-4-(3-bromophenyl)-3,4-dihydropyrimidin-2(1H)-thione 在 bis-triphenylphosphine-palladium(II) chloride 、 四(三苯基膦)钯 、 copper(I) bromide dimethylsulfide complex 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 48.0h， 生成 methyl 4-(biphenyl-3-yl)-6-methyl-2-(2-thiophenyl)-1,4-dihydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Optimized Liebeskind–Srogl coupling reaction between dihydropyrimidines and tributyltin compounds

  摘要：

  We developed an optimized Liebeskind-Srogl reaction in order to synthesize potentially biologically active 2-aryl-1,4-dihydropyrimidines. The pallado-catalyzed cross-coupling reaction between dihydropyrimidines and tributyltin derivatives appears particularly efficient (67-95% yields) when using CuBr.Me2S as the copper cofactor. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.03.067
• 作为产物：
  描述：

  间溴苯甲醛 、 乙酰乙酸甲酯 、 硫脲 在 organosulfonic acid-functionalized periodic mesoporous organosilicas 作用下， 以 neat (no solvent) 为溶剂， 反应 6.83h， 以89%的产率得到5-(methoxycarbonyl)-6-methyl-4-(3-bromophenyl)-3,4-dihydropyrimidin-2(1H)-thione
  参考文献：
  名称：

  通过控制催化剂的疏水/亲水表面平衡来提高三组分Biginelli与Hantzsch反应的选择性

  摘要：

  两种介孔固体酸SBA-15-PrSO 3 H 1，SBA-15-Ph-PrSO 3 H 2和基于周期性介孔有机硅（PMO）的固体酸Et-PMO-Me-PrSO的催化活性和选择性在无溶剂条件下，在醛，β-酮酸酯和尿素或硫脲的环境友好的单锅三组分Biginelli反应中比较了具有不同理化表面性质的3 H 3。在这些介孔固体酸催化剂中，3，在活性位点所在的纳米空间（介孔通道）中具有疏水/疏水平衡，在Biginelli反应中被发现是选择性更高的催化系统。它可以产生相应的3,4-二氢嘧啶-2-酮\硫酮（DHPM）5衍生物，产率高，选择性好。值得注意的是，在存在1的条件下进行苯甲醛，乙酸乙酰甲酯和尿素的三组分偶联反应时，会生成Hantzsch二氢吡啶4（≈37％）和Biginelli dihydropyrimidinone 5（≈49％）的混合物，而与2相同的反应（催化剂负载量也为1 mol％）提供了

  DOI：

  10.1002/cctc.201300739

文献信息

• Highly Enantioselective Organocatalytic Biginelli Reaction
  作者：Xiao-Hua Chen、Xiao-Ying Xu、Hua Liu、Lin-Feng Cun、Liu-Zhu Gong

  DOI：10.1021/ja065267y

  日期：2006.11.1

  aldehydes, thiourea or urea, and beta-keto esters. A new chiral phosphoric acid, derived from 3,3'-diphenyl-H8-binol, exhibited superior catalytic activity and enantioselectivity compared to its structural analogues, affording high enantioselectivities ranging from 85 to 97% ee with a wide scope of substrates. A metal-free preparation of optically active monastrol was achieved on the basis of the current

  首次评估了一系列基于二元醇和 H8-二元醇的磷酸催化醛、硫脲或尿素和 β-酮酯的 Biginelli 反应的能力。一种衍生自 3,3'-二苯基-H8-binol 的新型手性磷酸与其结构类似物相比表现出优异的催化活性和对映选择性，可提供 85% 至 97% ee 的高对映选择性，适用于广泛的底物。在现有工艺的基础上，实现了无金属制备旋光单星醇。
• Hydrophobicity-enhanced magnetic solid sulfonic acid: A simple approach to improve the mass transfer of reaction partners on the surface of the heterogeneous catalyst in water-generating reactions
  作者：Akbar Mobaraki、Barahman Movassagh、Babak Karimi

  DOI：10.1016/j.apcata.2013.12.018

  日期：2014.2
• The Efficient Synthesis of 3,4-Dihydropyrimidin-2-(1<i>H</i>)-Ones and Their Sulfur Derivatives with H₂SO₄ Immobilized on Activated Charcoal
  作者：Karim Akbari Dilmaghani、Behzad Zeynizadeh、Hadi Parasajam

  DOI：10.1080/10426507.2011.631644

  日期：2012.4.1

  Various 3,4-dihydropyrimidin-2-(1H)-ones (DHPMs) and their sulfur derivatives were efficiently synthesized by a one-pot cyclocondensation reaction of aromatic and aliphatic aldehydes, beta-dicarbonyl compounds and urea (or thiourea) in the presence of sulfuric acid immobilized on activated charcoal (133% w/w). The reactions were carried out in refluxing n-hexane-acetonitrile (2.5:0.5 mL) within 5-150 min to give 3,4-dihydropyrimidinones (or thiones) in high to excellent yields (81-97%).
• Fan, Xuesen; Zhang, Xinying; Zhang, Yongmin, Journal of Chemical Research - Part S, 2002, # 9, p. 436 - 438
  作者：Fan, Xuesen、Zhang, Xinying、Zhang, Yongmin

  DOI：——

  日期：——
• Optimized Liebeskind–Srogl coupling reaction between dihydropyrimidines and tributyltin compounds
  作者：Qi Sun、Franck Suzenet、Gérald Guillaumet

  DOI：10.1016/j.tetlet.2012.03.067

  日期：2012.5

  We developed an optimized Liebeskind-Srogl reaction in order to synthesize potentially biologically active 2-aryl-1,4-dihydropyrimidines. The pallado-catalyzed cross-coupling reaction between dihydropyrimidines and tributyltin derivatives appears particularly efficient (67-95% yields) when using CuBr.Me2S as the copper cofactor. (C) 2012 Elsevier Ltd. All rights reserved.