2-methyl-5-(naphthalen-1-yl)thiazol | 107559-03-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-methyl-5-(naphthalen-1-yl)thiazol
• 英文别名: 2-methyl-5-(naphthalen-1-yl)thiazole；2-methyl-5-[1]naphthyl-thiazole；2-Methyl-5-[1]naphthyl-thiazol；2-Methyl-5-(1-naphthalenyl)thiazole；2-methyl-5-naphthalen-1-yl-1,3-thiazole
• CAS: 107559-03-5
• 化学式: C₁₄H₁₁NS
• 分子量: 225.314
• InChiKey: RYVQDWJVUFUHIE-UHFFFAOYSA-N

物化性质

• 沸点：
  369.0±11.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-methyl-5-(naphthalen-1-yl)thiazol 、 3-ethyl-2-methylsulfanyl-benzothiazolium; iodide 、 对甲苯磺酸乙酯 在 乙醇 、 sodium acetate 作用下， 生成 (3-ethyl-benzothiazol-2-yl)-(3-ethyl-5-[1]naphthyl-thiazol-2-yl)-methinium ; iodide
  参考文献：
  名称：

  Sytsch, Ukrainskij Khimicheskij Zhurnal, 1958, vol. 24, p. 79,87

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(2-[1]naphthyl-2-oxo-ethyl)-acetamide 在 tetraphosphorus decasulfide 作用下， 生成 2-methyl-5-(naphthalen-1-yl)thiazol
  参考文献：
  名称：

  Sytsch, Ukrainskij Khimicheskij Zhurnal, 1958, vol. 24, p. 79,87

  摘要：

  DOI：

文献信息

• Camphyl-based α-diimine palladium complexes: highly efficient precatalysts for direct arylation of thiazoles in open-air
  作者：Fu-Min Chen、Dong-Dong Lu、Li-Qun Hu、Ju Huang、Feng-Shou Liu

  DOI：10.1039/c7ob00856b

  日期：——

  Based on the strategy of the development of phosphine-free palladium-catalyzed direct C–H arylation, a series of camphyl-based α-diimine palladium complexes bearing sterically bulky substituents were synthesized and characterized. The palladium complexes were applied for the cross-coupling of thiazole derivatives with aryl bromides. The effect of the sterically bulky substituent on the N-aryl moiety

  基于开发无膦钯催化的直接CHH芳基化的策略，合成并表征了一系列基于迷迭香的带有空间庞大取代基的α-二亚胺钯配合物。钯配合物用于噻唑衍生物与芳基溴化物的交叉偶联。筛选了体积庞大的取代基对N-芳基部分的影响以及反应条件。在最佳方案下，在露天条件下，在钯含量为0.2 mol％的情况下，可以将宽范围的芳基溴化物与噻唑平稳地偶联，并获得良好或优异的收率。
• Direct C-H bond (Hetero)arylation of thiazole derivatives at 5-position catalyzed by N-heterocyclic carbene palladium complexes at low catalyst loadings under aerobic conditions
  作者：Bei-Bei Ma、Xiao-Bing Lan、Dong-Sheng Shen、Feng-Shou Liu、Chang Xu

  DOI：10.1016/j.jorganchem.2019.06.016

  日期：2019.10

  synthesis of 5-(hetero)arylated thiazole derivatives via an N-heterocyclic carbene palladium (Pd-NHC) complex catalyzed direct C-H arylation reaction. Utilization of this methodology, the arylation of substituted thiazoles with (hetero)aryl bromides efficiently proceeded at low catalyst loading (0.1–0.05 mol%) and under aerobic conditions. A variety of (hetero)aryl bromides, even some strongly deactivated

  已经开发了一种高效且实用的方案，用于通过N-杂环卡宾钯（Pd-NHC）络合物催化的直接CH芳基化反应合成5-（杂）芳基噻唑衍生物。利用这种方法，在低催化剂负载量（0.1–0.05 mol％）和好氧条件下，取代的噻唑与（杂）芳基溴化物的芳基化反应有效进行。在最佳反应条件下，各种具有广泛官能团的（杂）芳基溴化物，甚至一些高度失活或高度拥挤的（杂）芳基溴化物均相容。在所有情况下，目标产品的产量均中等至定量。
• Developing Bis(imino)acenaphthene-Supported <i>N</i>-Heterocyclic Carbene Palladium Precatalysts for Direct Arylation of Azoles
  作者：Li-Qun Hu、Rong-Li Deng、Yan-Fen Li、Cui-Jin Zeng、Dong-Sheng Shen、Feng-Shou Liu

  DOI：10.1021/acs.organomet.7b00784

  日期：2018.1.22

  On the basis of the strategy of developing highly efficient protocol for Pd-catalyzed cross-coupling reactions, a series of bulky bis(imino)acenaphthene (BIAN)-supported Pd-PEPPSI complexes were synthesized, characterized, and applied in direct arylation of azoles. The effect of backbone and N-moieties on NHCs was evaluated, and the reaction conditions were optimized. It was found that the bulky Pd-PEPPSI complexes could be successfully employed in cross-coupling of (hetero)aryl bromides with azoles at a low palladium loading of 0.5-0.05 mol % under aerobic conditions, demonstrating the ease of manipulation without glovebox and handling of solvents.