4-(4-methoxyphenyl)-2-methyl-6-phenylpyrimidine | 67073-22-7

• 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: 4-(4-methoxyphenyl)-2-methyl-6-phenylpyrimidine
• 英文别名: 2-Methyl-4-(4-methoxyphenyl)-6-phenylpyrimidine
• CAS: 67073-22-7
• 化学式: C₁₈H₁₆N₂O
• 分子量: 276.338
• InChiKey: JKPPVRJODLCRAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 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：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲氧基苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 水 、 异丙醇 为溶剂， 反应 36.0h， 生成 4-(4-methoxyphenyl)-2-methyl-6-phenylpyrimidine
  参考文献：
  名称：

  Synthesis of 4-Aryl and Unsymmetrical 4,6-Diarylpyrimidines by the Suzuki-Miyaura Cross-Coupling Reaction

  摘要：

  A two-step procedure for the synthesis of 4-arylpyrimidines from inexpensive 4,6-dichloropyrimidine via a Suzuki-Miyaura/hydrodechlorination reaction sequence is described. The reaction resulted in the predominant formation of mono-arylated product. The cross-coupling of 4-chloro-6-substituted pyrimidines with various aryl/heteroarylboronic acids also furnished 4,6-disubstituted pyrimidines in acceptable yields.

  DOI：

  10.3987/com-18-13956

文献信息

• Synthesis and biological evaluation of pyrimidine bridged combretastatin derivatives as potential anticancer agents and mechanistic studies
  作者：Bhupinder Kumar、Praveen Sharma、Vivek Prakash Gupta、Madhu Khullar、Sandeep Singh、Nilambra Dogra、Vinod Kumar

  DOI：10.1016/j.bioorg.2018.02.027

  日期：2018.8

  evaluation of these compounds showed that selective cancer cell toxicity (in vitro using human lung and breast cancer cell lines) might be due to the inhibition of antioxidant enzymes instigating elevated ROS levels which triggers intrinsic apoptotic pathways. These compounds were found nontoxic to the normal human primary cells. Compound 4a, was found to be competitive inhibitor of colchicine and in

  使用MTT分析法设计，合成和评估了许多嘧啶桥联的康他汀衍生物，并评估了它们对乳腺癌（MCF-7）和肺癌（A549）细胞系的抗癌活性。大多数合成的化合物显示出良好的抗癌活性，其IC 50值在低微摩尔范围内。化合物4a和4p在该系列中最有效，对MCF7和A549癌细胞系的IC 50值分别为4.67 µM和3.38 µM和4.63 µM和3.71 µM。这些化合物的生物学评估表明，选择性癌细胞毒性（体外使用人肺癌和乳腺癌细胞系）可能是由于抗氧化剂酶的抑制导致ROS水平升高，从而触发了内在的凋亡途径。发现这些化合物对正常人原代细胞无毒。发现化合物4a是秋水仙碱的竞争性抑制剂，并且在微管蛋白结合测定中显示出与秋水仙碱相当的微管蛋白聚合抑制潜能。分子模型研究还表明，合成的化合物很好地适合秋水仙碱结合袋。
• Manganese‐Catalyzed Multicomponent Synthesis of Pyrimidines from Alcohols and Amidines
  作者：Nicklas Deibl、Rhett Kempe

  DOI：10.1002/anie.201611318

  日期：2017.2

  and C−N bond formations. β‐Alkylation reactions are used to multiply alkylate secondary alcohols with two different primary alcohols to synthesize fully substituted pyrimidines in a one‐pot process. Our PN5P‐Mn‐pincer complexes efficiently catalyze this multicomponent process. A comparison of our manganese catalysts with related cobalt catalysts indicates that manganese shows a reactivity similar to

  为从醇中合成不同的化合物以节省化石碳原料并减少CO 2排放的催化反应的发展非常重要。同样重要的是用大量可用的3d金属代替稀有贵金属。我们报道了由am和最多三种醇进行的锰络合物催化的嘧啶多组分合成。我们的反应通过缩合和脱氢步骤进行，从而形成选择性的C和C N键。β-烷基化反应用于将仲醇与两种不同的伯醇进行烷基化反应，以一锅法合成完全取代的嘧啶。我们的PN 5P-Mn-钳子复合物有效地催化了这种多组分过程。我们的锰催化剂与相关钴催化剂的比较表明，锰的反应性与铱相似，但与钴不同。该类比可用于进一步发展与锰配合物的（脱氢）反应。
• An efficient and convenient multicomponent reaction for the synthesis of 2-methyl-4,6-diarylpyrimidine under solvent-free conditions
  作者：Liangce Rong、Hongxia Han、Hong Jiang、Yisi Dai、Mengjie Zhuang、Minxiang Cao、Shujiang Tu

  DOI：10.1002/jhet.167

  日期：2009.9

  An efficient and convenient method for the preparation of 2-methyl-4,6-diarylpyrimidine derivatives by the multicomponent reactions of aromatic aldehydes, aromatic ketones, and acetamidine hydrochloride in the presence of sodium hydroxide under solvent-free conditions was reported. This method has the advantages of excellent yields, mild reaction conditions, easy workup, and environmentally friendly

  据报道，在无溶剂条件下，在氢氧化钠存在下，通过芳族醛，芳族酮和乙hydro盐酸盐的多组分反应，制备2-甲基-4,6-二芳基嘧啶衍生物的有效而便捷的方法。该方法的优点是收率高，反应条件温和，后处理容易和环境友好。J.杂环化​​学，（2009）。
• Synthesis of 4-Aryl and Unsymmetrical 4,6-Diarylpyrimidines by the Suzuki-Miyaura Cross-Coupling Reaction
  作者：Victor Snieckus、Gerald J. Tanoury、Sahaj Gupta、Jennifer A. Melanson、M Selim Hossain、Louis Vaillancourt、William A. Nugent

  DOI：10.3987/com-18-13956

  日期：——

  A two-step procedure for the synthesis of 4-arylpyrimidines from inexpensive 4,6-dichloropyrimidine via a Suzuki-Miyaura/hydrodechlorination reaction sequence is described. The reaction resulted in the predominant formation of mono-arylated product. The cross-coupling of 4-chloro-6-substituted pyrimidines with various aryl/heteroarylboronic acids also furnished 4,6-disubstituted pyrimidines in acceptable yields.