3-benzyloxy-5-iodoisothiazole | 669694-70-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzyloxy-5-iodoisothiazole
• 英文别名: 5-iodo-3-phenylmethoxy-1,2-thiazole
• CAS: 669694-70-6
• 化学式: C₁₀H₈INOS
• 分子量: 317.15
• InChiKey: GOUXLHJPFNPJRC-UHFFFAOYSA-N

物化性质

• 沸点：
  307.7±40.0 °C(Predicted)
• 密度：
  1.772±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  50.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-碘吡啶 、 3-benzyloxy-5-iodoisothiazole 在 bis-triphenylphosphine-palladium(II) chloride magnesium 、 zinc(II) chloride 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以48%的产率得到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
• 作为产物：
  描述：

  3-benzyloxyisothiazole 在 lithium diisopropyl amide 、 碘 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.25h， 以95%的产率得到3-benzyloxy-5-iodoisothiazole
  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.