1-[4-(2-propylthiazol-5-yl)phenyl]propan-1-one | 1109226-28-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[4-(2-propylthiazol-5-yl)phenyl]propan-1-one
• 英文别名: 4'-(2-propylthiazol-5-yl)propiophenone；1-[4-(2-Propyl-1,3-thiazol-5-yl)phenyl]propan-1-one
• CAS: 1109226-28-9
• 化学式: C₁₅H₁₇NOS
• 分子量: 259.372
• InChiKey: RVPJAUZRRFQAEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-正丙基噻唑 、 4'-溴苯丙酮 在 potassium acetate 、 palladium diacetate 作用下， 以 环戊基甲醚 为溶剂， 反应 24.0h， 以70%的产率得到1-[4-(2-propylthiazol-5-yl)phenyl]propan-1-one
  参考文献：
  名称：

  环戊基甲基醚：钯催化杂芳族化合物直接芳基化的替代溶剂

  摘要：

  某些醚，例如环戊基甲基醚和二正丁基醚，可以被认为是比N，N-二甲基乙酰胺（DMAc）或DMF更“绿色”的溶剂，可有利地用于钯催化的杂芳族化合物的直接芳基化。在125-150°C的条件下，在存在此类醚和仅0.5-1 mol％的钯催化剂的情况下，通过使用芳基溴化物作为偶联伙伴，噻唑，噻吩或呋喃的直接5-芳基化反应将以中等至高收率进行。

  DOI：

  10.1002/cssc.201000405

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。
• A Versatile Palladium/Triphosphane System for Direct Arylation of Heteroarenes with Chloroarenes at Low Catalyst Loading
  作者：David Roy、Sophal Mom、Matthieu Beaupérin、Henri Doucet、Jean-Cyrille Hierso

  DOI：10.1002/anie.201002987

  日期：2010.9.3

  of an air‐stable, robust palladium/tridentate phosphane catalyst in direct CH and CCl activation reactions is reported (see scheme; DMAc=N,N‐dimethylacetamide, TBAB=tetra‐n‐butylammonium bromide). Electron‐rich, electron‐poor, and polysubstituted furans (X=O), thiophenes (X=S), pyrroles (X=NR5), and thiazoles were arylated with chloroarenes in the presence of the catalyst.

  穿上它的环：在直接C中的使用对空气稳定的，坚固的钯/三齿磷烷催化剂 H和13 C 氯活化反应报道（参见方案;的DMAc = Ñ，Ñ二甲基乙酰胺，TBAB =四Ñ -丁基溴化铵）。在催化剂存在下，富电子，贫电子和多取代的呋喃（X = O），噻吩（X = S），吡咯（X = NR 5）和噻唑被氯芳烃芳基化。
• 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.