ethyl 2-ethoxy-4-methyl-6-phenylpyrimidine-5-carboxylate | 1245716-69-1

• 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-ethoxy-4-methyl-6-phenylpyrimidine-5-carboxylate
• CAS: 1245716-69-1
• 化学式: C₁₆H₁₈N₂O₃
• 分子量: 286.331
• InChiKey: IZOYOTJBTIYECY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  6-甲基-4-苯基-2-硫代-1,2,3,4-四氢嘧啶-5-羧酸乙酯 在 氧气 、 lithium perchlorate 、 caesium carbonate 作用下， 反应 7.0h， 生成 ethyl 2-ethoxy-4-methyl-6-phenylpyrimidine-5-carboxylate
  参考文献：
  名称：

  Metal- and Oxidant-Free Electrochemical Oxidative Desulfurization C–O Coupling of Thiourea-Type Compounds with Alcohols

  摘要：

  一种高效的脱硫C-O偶联反应是在电化学氧化条件下开发的，该反应使用3,4-二氢嘧啶-2(1H)-硫酮（包括硫脲）与醇的反应。在这种反应中，不需要过渡金属催化剂和添加剂，醇既是溶剂又是烷氧基供体。

  DOI：

  10.1055/s-0039-1690837

文献信息

• Aerobic copper-promoted oxidative dehydrosulfurative carbon–oxygen cross-coupling of 3,4-dihydropyrimidine-1<i>H</i>-2-thiones with alcohols
  作者：Jihong Lee、Yujeong Kwon、Dong-Chan Lee、Jeong-Hun Sohn

  DOI：10.1039/d1ra07713a

  日期：——

  A wide range of readily available DHPMs and alcohols makes the presented reaction an attractive method to access biologically valuable 2-alkoxypyrimidine derivatives with rapid diversification.

  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。
• Boric Ester and Thiourea as Coupling Partners in a Copper-Mediated Oxidative Dehydrosulfurative Carbon–Oxygen Cross-Coupling Reaction
  作者：Hyeji Kim、Jihong Lee、Hyunik Shin、Jeong-Hun Sohn

  DOI：10.1021/acs.orglett.8b00502

  日期：2018.4.6

  dehydrosulfurative carbon–oxygen cross-coupling reaction with boric ester and six-membered cyclic thiourea for single-step production of densely substituted 2-alkoxypyrimidines incorporated in a privileged scaffold is described. This is the first demonstration of boric ester acting as an alkoxy donor in a metal-catalyzed coupling reaction to produce ether. The reaction method offers a shortcut for producing

  描述了一种与硼酸酯和六元环硫脲进行铜介导的氧化脱氢硫碳-氧交叉偶联反应，用于一步制备高密度取代的2-烷氧基嘧啶的方法，该方法被并入了优先的支架中。这是硼酸酯在金属催化的偶合反应中生成醚的过程中首次证明烷氧基供体。该反应方法为快速多样化生产2-烷氧基嘧啶衍生物提供了捷径，并扩大了硼酸酯的应用范围和Liebeskind-Srogl型反应的范围。
• Synthesis of 2-Substituted Pyrimidines via Cross-Coupling Reaction of Pyrimidin-2-yl Sulfonates with Nucleophiles in Polyethylene Glycol 400
  作者：Xi-Cun Wang、Guo-Jun Yang、Zheng-Jun Quan、Peng-Yan Ji、Jun-Ling Liang、Rong-Guo Ren

  DOI：10.1055/s-0030-1258080

  日期：2010.7

  A mild and rapid procedure to the synthesis of 2-substituted pyrimidines was developed via sequential functionalization of easily available Biginelli 3,4-dihydropyrimidine-2(1H)-ones via oxidation, esterification, followed by cross-coupling reaction of pyrimidin-2-yl sulfonates with N, S, and O nucleophiles in PEG-400 as a green reaction medium at room temperature.

  通过氧化、酯化以及嘧啶-2-的交叉偶联反应对容易获得的 Biginelli 3,4-二氢嘧啶-2(1H)-酮进行顺序功能化，开发了一种温和且快速的合成 2-取代嘧啶的方法在室温下作为绿色反应介质，在 PEG-400 中使用 N、S 和 O 亲核试剂制备基磺酸盐。
• Synthesis of C2-functionalized pyrimidines from 3,4-dihydropyrimidin-2(1H)-ones by the Mitsunobu coupling reaction
  作者：Xi-Cun Wang、Guo-Jun Yang、Xiao-Dong Jia、Zhang Zhang、Yu-Xia Da、Zheng-Jun Quan

  DOI：10.1016/j.tet.2011.02.046

  日期：2011.5

  The Biginelli 3,4-dihydropyrimidin-2(1H)-one was converted to various C2-multifunctionalized pyrimidines via the dehydrogenation and Mitsunobu reaction using amines, alcohols, phenols and carboxylic acids as nucleophiles. A possible mechanism was also proposed to rationalize the formation of products.

  通过使用胺，醇，酚和羧酸作为亲核试剂的脱氢和Mitsunobu反应，将Biginelli 3,4-dihydropyrimidin-2（1 H）-one转化为各种C 2-多官能嘧啶。还提出了一种可能的机制来合理化产品的形成。
• Facile transformation of Biginelli pyrimidin-2(1H)-ones to pyrimidines. In vitro evaluation as inhibitors of Mycobacterium tuberculosis and modulators of cytostatic activity
  作者：Kamaljit Singh、Kawaljit Singh、Baojie Wan、Scott Franzblau、Kelly Chibale、Jan Balzarini

  DOI：10.1016/j.ejmech.2011.03.010

  日期：2011.6

  A series of pyrimidine derivatives bearing amine substituents at C-2 position were obtained from Biginelli 3,4-dihydropyrimidin-2(1H)-ones and the effect of structural variation on anti-TB activity against Mycobacterium tuberculosis H(37)Rv strain and antiviral activity in a series of cell cultures was evaluated. While the compounds were found to possess structure dependent cytostatic activity, these were not found to be efficient inhibitors of M. tuberculosis nor did they inhibit a broad variety of DNA or RNA viruses in cell culture. (C) 2011 Elsevier Masson SAS. All rights reserved.