2-methoxy-6-((1-phenyl-1H-tetrazol-5-yl)oxy)phenyl 4-methylbenzenesulfonate | 137669-12-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-methoxy-6-((1-phenyl-1H-tetrazol-5-yl)oxy)phenyl 4-methylbenzenesulfonate
• 英文别名: Toluene-4-sulfonic acid 2-methoxy-6-(1-phenyl-1H-tetrazol-5-yloxy)-phenyl ester
• CAS: 137669-12-6
• 化学式: C₂₁H₁₈N₄O₅S
• 分子量: 438.464
• InChiKey: YVLMNVGCTWAYCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  105.43
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-methoxy-6-((1-phenyl-1H-tetrazol-5-yl)oxy)phenyl 4-methylbenzenesulfonate 在 镍 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 2-tosyloxyanisole
  参考文献：
  名称：

  The regioselective cleavage of aryl tosylates by electrochemical reduction

  摘要：

  The electrochemical reductions of eight bis(tosyloxy)benzanoid compounds were studied as a method for the regioselective cleavage of aryl tosylates. For the methyl bis(tosyloxy)benzoate isomers, a strong preference was observed for cleavage of the tosyl group in conjugation with the electron-withdrawing ester moiety. Thus it was possible to selectively cleave tosyl groups to the ortho or para positions over tosyl groups at the meta positions. The bis(tosyloxy)anisole isomers displayed the opposite regioselectivity favoring cleavage of tosyl groups that were meta to the electron-donating methoxy substituent. The general electrochemical process for the reduction of aryl tosylates has been shown to be selective, high yielding, and reproducible on gram quantities.

  DOI：

  10.1021/jo00029a010
• 作为产物：
  描述：

  2,3-bis(tosyloxy)anisole 在 potassium tert-butylate 作用下， 以 乙腈 为溶剂， 生成 2-methoxy-6-((1-phenyl-1H-tetrazol-5-yl)oxy)phenyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  The regioselective cleavage of aryl tosylates by electrochemical reduction

  摘要：

  The electrochemical reductions of eight bis(tosyloxy)benzanoid compounds were studied as a method for the regioselective cleavage of aryl tosylates. For the methyl bis(tosyloxy)benzoate isomers, a strong preference was observed for cleavage of the tosyl group in conjugation with the electron-withdrawing ester moiety. Thus it was possible to selectively cleave tosyl groups to the ortho or para positions over tosyl groups at the meta positions. The bis(tosyloxy)anisole isomers displayed the opposite regioselectivity favoring cleavage of tosyl groups that were meta to the electron-donating methoxy substituent. The general electrochemical process for the reduction of aryl tosylates has been shown to be selective, high yielding, and reproducible on gram quantities.

  DOI：

  10.1021/jo00029a010