ethyl 2-(4-chlorophenylthio)-4-methyl-6-phenylpyrimidine-5-carboxylate | 1421829-30-2

• 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 2-(4-chlorophenylthio)-4-methyl-6-phenylpyrimidine-5-carboxylate
• 英文别名: Ethyl 2-(4-chlorophenyl)sulfanyl-4-methyl-6-phenylpyrimidine-5-carboxylate
• CAS: 1421829-30-2
• 化学式: C₂₀H₁₇ClN₂O₂S
• 分子量: 384.886
• InChiKey: VVPNJTCOFIZDHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  77.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯甲醛 在 盐酸 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 ethyl 2-(4-chlorophenylthio)-4-methyl-6-phenylpyrimidine-5-carboxylate
  参考文献：
  名称：

  Nano copper oxide mediated ligand-free C–S cross-coupling and concomitant oxidative aromatization of 4-aryl-3,4-dihydropyrimidin-2(1H)-thione with diaryliodonium salts

  摘要：

  A wide range of Biginelli 4-aryl-3,4-dihydropyrimidin-2(1H)-thiones undergo ligand-free C-S cross-coupling with diaryliodonium triflates in the presence of CuO nanoparticles with the concomitant oxidative aromatization to form highly substituted 2-(thioaryl)pyrimidine. The nano CuO catalyst can be recycled and reused three times without any significant loss of catalytic activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.131

文献信息

• Chemo-Controlled Cross-Coupling of Di(hetero)aryl Disulfides with Grignard Reagents: CC<i>vs.</i>CS Bond Formation
  作者：Bao-Xin Du、Zheng-Jun Quan、Yu-Xia Da、Zhang Zhang、Xi-Cun Wang

  DOI：10.1002/adsc.201400980

  日期：2015.4.13

  A general protocol for the chemoselectivity‐controlled CC and CS coupling reactions of di(hetero)aryl disulfides with Grignard reagents catalyzed by ferrocene and palladium acetate has been developed. Ferrocene favored the formation of CS coupled products at low temperature, whereas CC bond couplings were favored when palladium acetate was used. All the reactions proceeded with excellent chemoselectivity

  已开发了二（杂）芳基二硫化物与二茂铁和乙酸钯催化的格氏试剂的化学选择性控制的CC和CS偶联反应的通用方案。二茂铁有利于在低温下形成CS偶联产物，而当使用乙酸钯时则有利于CC键偶联。在温和的条件下，所有反应均以优异的化学选择性和良好的收率进行，并产生了具有吡啶和嘧啶支架的分子库。
• C-O and C-S coupling reaction of 1,2-di(pyrimidin-2-yl) disulfides with phenols/thiophenols promoted by copper(I) chloride
  作者：Ping Zhang、Yan Guo、Zheng-Jun Quan

  DOI：10.1002/hc.21397

  日期：2017.9

  C-O and C-S bonds formation by the cross-coupling reaction of 1,2-di(pyrimidin-2-yl) disulfides with phenols/thiophenols promoted by copper(I) chloride was established. It was discovered that variously substituted di(hetero)aryl disulfides and phenols were well tolerated. This strategy is the conversion of disulfides into hetero-aryl ethers and thioethers by a copper-promoted chemoselective C-S bond cleavage

  建立了通过氯化铜（I）促进的 1,2-二（嘧啶-2-基）二硫化物与苯酚/苯硫酚的交叉偶联反应形成 CO 和 CS 键的有效方案。发现各种取代的二（杂）芳基二硫化物和酚类具有良好的耐受性。该策略是通过铜促进的二硫化物的化学选择性 CS 键裂解，将二硫化物转化为杂芳基醚和硫醚。