3-benzyloxy-5-(2-pyridyl)isothiazole

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzyloxy-5-(2-pyridyl)isothiazole
• 英文别名: 3-Phenylmethoxy-5-pyridin-2-yl-1,2-thiazole
• 化学式: C₁₅H₁₂N₂OS
• 分子量: 268.339
• InChiKey: LUESEYUQRLBKHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-benzyloxyisothiazole 在 magnesium 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 17.25h， 生成 3-benzyloxy-5-(2-pyridyl)isothiazole
  参考文献：
  名称：

  Synthesis of Aryl- and Heteroaryl-Substituted 3-Benzyloxyisothiazoles via Suzuki and Negishi Cross-Coupling Reactions

  摘要：

  Introduction of aryl and heteroaryl substituents into the 5-position of 3-benzyloxyisothiazole (1) using palladium-catalyzed Suzuki and Negishi cross-coupling reactions was investigated. Attempts to generate synthetically viable nucleophilic species from I for Suzuki- or Negishi-type cross-couplings were unsuccessful. However, using 3-benzyloxy-5-iodoisothiazole 2 as an intermediate, a range of aromatic and heteroaromatic substituents were successfully introduced under Suzuki or Negishi cross-coupling conditions in good to excellent yields.

  DOI：

  10.1021/jo035578g

文献信息

• Synthesis of Aryl- and Heteroaryl-Substituted 3-Benzyloxyisothiazoles via Suzuki and Negishi Cross-Coupling Reactions
  作者：Birgitte H. Kaae、Povl Krogsgaard-Larsen、Tommy N. Johansen

  DOI：10.1021/jo035578g

  日期：2004.2.1

  Introduction of aryl and heteroaryl substituents into the 5-position of 3-benzyloxyisothiazole (1) using palladium-catalyzed Suzuki and Negishi cross-coupling reactions was investigated. Attempts to generate synthetically viable nucleophilic species from I for Suzuki- or Negishi-type cross-couplings were unsuccessful. However, using 3-benzyloxy-5-iodoisothiazole 2 as an intermediate, a range of aromatic and heteroaromatic substituents were successfully introduced under Suzuki or Negishi cross-coupling conditions in good to excellent yields.