methyl 2,4-bis(tosyloxy)benzoate | 137668-92-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2,4-bis(tosyloxy)benzoate
• 英文别名: Methyl 2,4-bis[(4-methylbenzene-1-sulfonyl)oxy]benzoate；methyl 2,4-bis-(4-methylphenyl)sulfonyloxybenzoate
• CAS: 137668-92-9
• 化学式: C₂₂H₂₀O₈S₂
• 分子量: 476.528
• InChiKey: PLKYRQWFJIEHBB-UHFFFAOYSA-N

物化性质

• 沸点：
  657.9±55.0 °C(Predicted)
• 密度：
  1.372±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2,4-bis(tosyloxy)benzoate 在 镍 potassium tert-butylate 、 氢气 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 生成 methyl 2-(tosyloxy)benzoate
  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：

  2,4-二羟基苯甲酸甲酯 、 1-对甲基苯磺酰咪唑 在 TEA 、 三氟甲烷磺酸甲酯 作用下， 以 四氢呋喃 为溶剂， 以96%的产率得到methyl 2,4-bis(tosyloxy)benzoate
  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

文献信息

• The regioselective cleavage of aryl tosylates by electrochemical reduction
  作者：Edgar R. Civitello、Henry Rapoport

  DOI：10.1021/jo00029a010

  日期：1992.1

  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.