5-(4-tert-butylphenyl)-2-n-propylthiazole | 1005759-21-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(4-tert-butylphenyl)-2-n-propylthiazole
• 英文别名: 5-(4-tert-butylphenyl)-2-propylthiazole；5-(4-Tert-butylphenyl)-2-propyl-1,3-thiazole
• CAS: 1005759-21-6
• 化学式: C₁₆H₂₁NS
• 分子量: 259.415
• InChiKey: DSESVQOQSCOXFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-正丙基噻唑 、 4-tert-butylphenyl triflate 在 palladium diacetate potassium acetate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以58%的产率得到5-(4-tert-butylphenyl)-2-n-propylthiazole
  参考文献：
  名称：

  芳基三氟甲磺酸酯：通过Pd催化的CH活化功能化使杂芳基衍生物直接芳基化的有用偶联伙伴。

  摘要：

  发现芳基三氟甲磺酸酯是通过CH活化-官能化的钯催化的杂芳族化合物的直接芳基化的伙伴。反应条件和催化剂对产率具有决定性的影响。使用KOAc作为碱和DMF作为溶剂的PPh3和Pd（OAc）2组合系统可中等至高收率地促进选择性2-或5-芳基化。几种杂芳族化合物如呋喃，噻吩，噻唑或恶唑衍生物已被成功使用。芳基三氟甲磺酸酯的电子性质也对偶联产物的产率具有决定性的影响。富电子芳基三氟甲磺酸酯给出令人满意的结果，而贫电子芳基三氟甲磺酸导致苯酚的形成。

  DOI：

  10.1039/b715235c

文献信息

• Ligand-Free Palladium-Catalyzed Direct Arylation of Thiazoles at Low Catalyst Loadings
  作者：Julien Roger、Franc Požgan、Henri Doucet

  DOI：10.1021/jo802360d

  日期：2009.2.6

  Ligand-free Pd(OAc)2 was found to catalyze very efficiently the direct arylation of thiazole derivatives under very low catalyst concentration. By using activated aryl bromides, the reaction can be performed employing as little as 0.1−0.001 mol % catalyst. With such substrates, this procedure is economically and environmentally attractive. On the other hand, in the presence of more challenging substrates

  发现无配体的Pd（OAc）2在非常低的催化剂浓度下非常有效地催化噻唑衍生物的直接芳基化。通过使用活化的芳基溴化物，可以使用低至0.1-0.001 mol％的催化剂进行反应。对于这样的基板，该程序在经济和环境上都是有吸引力的。另一方面，在更具挑战性的底物（例如某些高度失活或高度拥挤的芳基溴化物）的存在下，获得的结果令人失望。
• Palladium-catalysed direct arylations of heteroaromatics using more eco-compatible solvents pentan-1-ol or 3-methylbutan-1-ol
  作者：Souhila Bensaid、Nouria Laidaoui、Douniazad El Abed、Soufi Kacimi、Henri Doucet

  DOI：10.1016/j.tetlet.2011.01.084

  日期：2011.3

  The palladium-catalysed direct coupling of aryl halides with heteroaromatics in greener solvents than DMF or DMAc, which are often employed for such couplings, would be a considerable advantage for both industrial application and sustainable development. We observed that a range of aryl bromides undergoe coupling via C-H bond activation/functionalisation reaction of thiazoles or imidazoles in moderate to good yields using pentan-1-ol or 3-methylbutan-1-ol as the solvents. Pentan-1-ol and 3-methylbutan-1-ol are less toxic than DMF or DMAc, moreover they are bioresources as they can be obtained by fermentation. Therefore, these reaction conditions are certainly more eco-compatible than those generally employed for such couplings. (C) 2011 Elsevier Ltd. All rights reserved.
• Aryl triflates: useful coupling partners for the direct arylation of heteroaryl derivatives via Pd-catalyzed C–H activation–functionalization
  作者：Julien Roger、Henri Doucet

  DOI：10.1039/b715235c

  日期：——

  Aryl triflates were found to be suitable partners for the palladium catalyzed direct arylation of heteroaromatics via C-H activation-functionalization. The reaction conditions and the catalyst have a determining influence on the yields. The system combining PPh3 and Pd(OAc)2 using KOAc as base and DMF as solvent promotes the selective 2- or 5-arylations in moderate to high yields. Several heteroaromatics

  发现芳基三氟甲磺酸酯是通过CH活化-官能化的钯催化的杂芳族化合物的直接芳基化的伙伴。反应条件和催化剂对产率具有决定性的影响。使用KOAc作为碱和DMF作为溶剂的PPh3和Pd（OAc）2组合系统可中等至高收率地促进选择性2-或5-芳基化。几种杂芳族化合物如呋喃，噻吩，噻唑或恶唑衍生物已被成功使用。芳基三氟甲磺酸酯的电子性质也对偶联产物的产率具有决定性的影响。富电子芳基三氟甲磺酸酯给出令人满意的结果，而贫电子芳基三氟甲磺酸导致苯酚的形成。