2-(2-propylthiazol-5-yl)benzonitrile

• 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: 2-(2-propylthiazol-5-yl)benzonitrile
• 英文别名: 2-(2-Propyl-1,3-thiazol-5-yl)benzonitrile；2-(2-propyl-1,3-thiazol-5-yl)benzonitrile
• 化学式: C₁₃H₁₂N₂S
• 分子量: 228.318
• InChiKey: ZKYUTEGVLATCJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  64.9
• 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 、 邻氯苯腈 在 PdCl(dppb)(C₃H₅) potassium acetate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 15.0h， 以41%的产率得到2-(2-propylthiazol-5-yl)benzonitrile
  参考文献：
  名称：

  活化芳基氯化物：在钯催化的 CH 活化/功能化反应中与 2-取代噻唑偶联的有用伙伴

  摘要：

  在通过 CH 活化与杂芳烃偶联反应中，芳基氯是非常罕见的伙伴。我们在本文中报道，空气稳定的 PdCl(dppb)(C3H5) 配合物只要 1 mol% 即可催化缺电子芳基氯化物与 2-取代噻唑衍生物的直接偶联。可以容忍芳基氯上的一系列官能团，例如乙酰基、甲酰基、酯、硝基、腈或三氟甲基。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  DOI：

  10.1002/ejic.200700420

文献信息

• Cyclopentyl Methyl Ether: An Alternative Solvent for Palladium-Catalyzed Direct Arylation of Heteroaromatics
  作者：Kassem Beydoun、Henri Doucet

  DOI：10.1002/cssc.201000405

  日期：2011.4.18

  Some ethers, such as cyclopentyl methyl ether and di‐n‐butyl ether, which can be considered as “greener” solvents than N,N‐dimethylacetamide (DMAc) or DMF, can be advantageously employed for the palladium‐catalyzed direct arylation of heteroaromatics. In the presence of such ethers and only 0.5–1 mol % of palladium catalysts at 125–150 °C, the direct 5‐arylation of thiazoles, thiophenes, or furans

  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。
• 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。
• Carbonates: eco-friendly solvents for palladium-catalysed direct arylation of heteroaromatics
  作者：Jia Jia Dong、Julien Roger、Cécile Verrier、Thibaut Martin、Ronan Le Goff、Christophe Hoarau、Henri Doucet

  DOI：10.1039/c0gc00229a

  日期：——

  The palladium-catalysed direct 2-, 4- or 5-arylation of a wide range of heteroaromatics with aryl halides proceed in moderate to good yields using the eco-friendly solvents carbonates. The best yields were obtained using benzoxazole or thiazole derivatives. The arylation of furan, thiophene, pyrrole, imidazole or isoxazole derivatives was found to require a more elevated reaction temperature.

  这 钯环保型芳烃卤化物催化的各种杂芳族化合物与芳基卤化物的直接2-，4-或5-芳基化反应均能以中等至良好的收率进行 溶剂碳酸盐。使用以下方法可获得最佳产量苯并恶唑 或者 噻唑衍生品。这芳基化 的 呋喃， 噻吩， 吡咯， 咪唑 或者 异恶唑 发现衍生物需要更高的反应温度。
• 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.
• Activated Aryl Chlorides: Useful Partners for the Coupling with 2‐Substituted Thiazoles in the Palladium‐Catalysed C‐H Activation/Functionalisation Reaction
  作者：Aditya L. Gottumukkala、Henri Doucet

  DOI：10.1002/ejic.200700420

  日期：2007.8

  C-H activation. We report herein that as little as 1 mol-% of the air-stable PdCl(dppb)(C3H5) complex catalyses the direct coupling of electron-deficient aryl chlorides with 2-substituted thiazole derivatives. A range of functionalities on the aryl chloride such as acetyl, formyl, ester, nitro, nitrile or trifluoromethyl is tolerated. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  在通过 CH 活化与杂芳烃偶联反应中，芳基氯是非常罕见的伙伴。我们在本文中报道，空气稳定的 PdCl(dppb)(C3H5) 配合物只要 1 mol% 即可催化缺电子芳基氯化物与 2-取代噻唑衍生物的直接偶联。可以容忍芳基氯上的一系列官能团，例如乙酰基、甲酰基、酯、硝基、腈或三氟甲基。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)