ethyl 4-methyl-6-phenyl-2-(p-tolyloxy)pyrimidine-5-carboxylate | 1048007-30-2

• 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 4-methyl-6-phenyl-2-(p-tolyloxy)pyrimidine-5-carboxylate
• 英文别名: ethyl 4-methyl-2-(4-methylphenoxy)-6-phenylpyrimidine-5-carboxylate
• CAS: 1048007-30-2
• 化学式: C₂₁H₂₀N₂O₃
• 分子量: 348.401
• InChiKey: ZPCGTPAAHXJEFD-UHFFFAOYSA-N

物化性质

• 沸点：
  525.5±60.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  61.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对甲酚 、 6-甲基-4-苯基-2-硫代-1,2,3,4-四氢嘧啶-5-羧酸乙酯 在 copper diacetate 、 silver carbonate 作用下， 以 甲苯 为溶剂， 以51%的产率得到ethyl 4-methyl-6-phenyl-2-(p-tolyloxy)pyrimidine-5-carboxylate
  参考文献：
  名称：

  Aerobic copper-promoted oxidative dehydrosulfurative carbon–oxygen cross-coupling of 3,4-dihydropyrimidine-1H-2-thiones with alcohols

  摘要：

  一系列易得的DHPMs和醇使得所呈现的反应成为一种吸引人的方法，可用于快速多样化地获得具有生物学价值的2-烷氧基嘧啶衍生物。

  DOI：

  10.1039/d1ra07713a

文献信息

• Cross-Coupling Reactions of Pyrimidin-2-yl Sulfonates with Phenols and Anilines: An Efficient Approach to C2-Functionalized Pyrimidines
  作者：Zhengjun Quan、Fuqiang Jing、Zhang Zhang、Yuxia Da、Xicun Wang

  DOI：10.1002/cjoc.201300536

  日期：2013.12

  Pyrimidin‐2‐yl sulfonates, as an efficient reaction partner, which can be easily prepared from cheap commercial materials, were coupled with phenols and anilines to give a wide array of C2‐aryloxy‐ and arylaminopyrimidines in good to excellent yields under mild reaction conditions.

  嘧啶-2-基磺酸盐作为一种有效的反应伙伴，可以轻松地从廉价的商业原料中制备，并与苯酚和苯胺偶联，在温和的反应条件下，以良好的收率获得了良好的C2-芳氧基和芳基氨基嘧啶种类繁多的收率。 。
• Pd-Catalyzed Direct Arylation of Tautomerizable Heterocycles with Aryl Boronic Acids via C−OH Bond Activation Using Phosphonium Salts
  作者：Fu-An Kang、Zhihua Sui、William V. Murray

  DOI：10.1021/ja804804p

  日期：2008.8.27

  first direct arylation via C-OH bond activation of tautomerizable heterocycles has been achieved using phosphonium salts, on the basis of a combination of the phosphonium coupling and Suzuki-Miyaura cross-coupling conditions. Optimal reaction condition is obtained through screening of phosphonium salts, Pd catalysts, and bases. The direct arylation via C-OH bond activation tolerates a variety of tautomerizable

  基于鏻偶联和 Suzuki-Miyaura 交叉偶联条件的组合，使用鏻盐实现了通过 C-OH 键活化可互变异构的杂环的第一个直接芳基化。通过鏻盐、钯催化剂和碱的筛选，获得最佳反应条件。通过 C-OH 键活化的直接芳基化耐受各种可互变异构的杂环和芳基硼酸。Pd 催化的鏻偶联机制被提议通过多米诺七步法进行，包括前所未有的杂环-Pd(II)-鏻物种。
• 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。
• Oxidative Dehydrosulfurative Carbon–Oxygen Cross-Coupling of 3,4-Dihydropyrimidine-2-thiones with Aryl Alcohols
  作者：Trong Nguyen Huu Phan、Jihong Lee、Hyunik Shin、Jeong-Hun Sohn

  DOI：10.1021/acs.joc.1c00273

  日期：2021.4.2