5-(furan-3-yl)-2-methylbenzo[d]thiazole | 1020540-68-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 5-(furan-3-yl)-2-methylbenzo[d]thiazole
• 英文别名: 5-furan-3-yl-2-methylbenzothiazole；5-(Furan-3-yl)-2-methyl-1,3-benzothiazole
• CAS: 1020540-68-4
• 化学式: C₁₂H₉NOS
• 分子量: 215.276
• InChiKey: YEXHBNBNKPNDMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  54.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-methylbenzo[d]thiazol-5-yl methanesulfonate 、 potassium 3-furyltrifluoroborate 在 bis(1,5-cyclooctadiene)nickel (0) 、 potassium phosphate 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 4.0h， 以77%的产率得到5-(furan-3-yl)-2-methylbenzo[d]thiazole
  参考文献：
  名称：

  Nickel-Catalyzed C−O Activation of Phenol Derivatives with Potassium Heteroaryltrifluoroborates

  摘要：

  A general method based on nickel-catalyzed C-O activation of various phenol derivatives with potassium (hetero)aryltrifluoroborates has been developed. A large number of heterobiaryls can be easily obtained with yields up to 99% using methanesulfonate cross-coupling partners.

  DOI：

  10.1021/ol101592r

文献信息

• Efficient Suzuki−Miyaura Coupling of (Hetero)aryl Chlorides with Thiophene- and Furanboronic Acids in Aqueous <i>n-</i>Butanol
  作者：Christoph A. Fleckenstein、Herbert Plenio

  DOI：10.1021/jo8001886

  日期：2008.4.1

  An efficient Suzuki cross-coupling protocol enables the reaction of N-hetero and normal aryl chlorides with thiophene- and furanboronic acids. Coupling is effected in aqueous n-butanol as the solvent in near quantitative yield with a catalyst loading of 0.1 - 1 mol %. For heterocyclic substrates aqueous catalysis is found to be more efficient than Suzuki coupling under anhydrous conditions. The developed Suzuki coupling procedure utilizes biodegradable solvents and is useful for large scale reactions, as it includes the facile product separation from a biphasic solvent mixture without the need for additional organic solvents during workup.
• Nickel-Catalyzed C−O Activation of Phenol Derivatives with Potassium Heteroaryltrifluoroborates
  作者：Gary A. Molander、Floriane Beaumard

  DOI：10.1021/ol101592r

  日期：2010.9.17

  A general method based on nickel-catalyzed C-O activation of various phenol derivatives with potassium (hetero)aryltrifluoroborates has been developed. A large number of heterobiaryls can be easily obtained with yields up to 99% using methanesulfonate cross-coupling partners.