4-(3-methoxyphenyl)-2-methyl-5-phenylthiazole | 239448-53-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(3-methoxyphenyl)-2-methyl-5-phenylthiazole
• 英文别名: 4-(3-Methoxyphenyl)-2-methyl-5-phenyl-1,3-thiazole
• CAS: 239448-53-4
• 化学式: C₁₇H₁₅NOS
• 分子量: 281.378
• InChiKey: WFEPPROOZLVKQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  50.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3-methoxyphenyl)-2-methyl-5-phenylthiazole 在 三氟化硼乙醚 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 为溶剂， 以5%的产率得到5-Methoxy-2-methyl-phenanthro[9,10-d]thiazole
  参考文献：
  名称：

  An efficient synthesis of phenanthro-fused thiazoles by a non-phenolic oxidative coupling procedure of 4,5-diarylthiazoles

  摘要：

  A concise synthesis of the title compounds 6 is accomplished in high overall yield in a two step process starting from bromoketone 4. A thiazole ring formation and a non-phenolic oxidative coupling reaction using PIFA are features of me described synthesis. An exploration of the electronic requirements and the regioselectivity of the cyclization is also presented. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00982-x
• 作为产物：
  描述：

  3-甲氧基苯乙酮 在 溴 作用下， 生成 4-(3-methoxyphenyl)-2-methyl-5-phenylthiazole
  参考文献：
  名称：

  An efficient synthesis of phenanthro-fused thiazoles by a non-phenolic oxidative coupling procedure of 4,5-diarylthiazoles

  摘要：

  A concise synthesis of the title compounds 6 is accomplished in high overall yield in a two step process starting from bromoketone 4. A thiazole ring formation and a non-phenolic oxidative coupling reaction using PIFA are features of me described synthesis. An exploration of the electronic requirements and the regioselectivity of the cyclization is also presented. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00982-x

文献信息

• A Simple Route to New Phenanthro- and Phenanthroid-Fused Thiazoles by a PIFA-Mediated (Hetero)biaryl Coupling Reaction
  作者：Isabel Moreno、Imanol Tellitu、Esther Domínguez、Raúl SanMartín

  DOI：10.1002/1099-0690(200207)2002:13<2126::aid-ejoc2126>3.0.co;2-a

  日期：2002.7

  An application of the PIFA-mediated [PIFA: phenyliodine(III) bis(trifluoroacetate)] biaryl coupling reaction is presented and extended to the formation of heterobiaryl connections. A preliminary study of the scope and limitations of this procedure was carried out in the synthesis of phenanthroids 11 from a series of phenethyl-substituted heterocycles 10. It was observed that in some cases a competitive

  提出了 PIFA 介导的 [PIFA: 苯基碘 (III) 双 (三氟乙酸酯)] 联芳基偶联反应的应用，并将其扩展到形成杂联芳基连接。在从一系列苯乙基取代的杂环 10 合成拟类化合物 11 时，对该程序的范围和局限性进行了初步研究。观察到在某些情况下发生了竞争性二聚化过程。还发现，如果芳环与 1,2-二芳基乙烷骨架稠合，则偶联步骤可以有效地扩展到更多的实例，如 23 和 30。一系列 4,5-的合成因此，进行二芳基噻唑 23a-g 以探索 PIFA 介导的非酚类偶联反应的电子要求和区域选择性。当将相同的程序应用于芳基-杂芳基噻唑 30 时，以良好的总产率获得了一系列菲类稠合的噻唑 31。据我们所知，以前没有报道过这种类型的氧化芳基-杂芳基偶联反应。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)