2-Methoxy-2-methyl-thiopropionic acid S-(4-bromo-phenyl) ester | 286410-30-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: 2-Methoxy-2-methyl-thiopropionic acid S-(4-bromo-phenyl) ester
• 英文别名: S-(4-bromophenyl) 2-methoxy-2-methylpropanethioate
• CAS: 286410-30-8
• 化学式: C₁₁H₁₃BrO₂S
• 分子量: 289.193
• InChiKey: MXLZIUDQFUCEGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Methoxy-2-methyl-thiopropionic acid S-(4-bromo-phenyl) ester 在 四(三苯基膦)钯 sodium hydroxide 、 potassium phosphate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 19.5h， 生成 4'-methyl-4-mercaptobiphenyl
  参考文献：
  名称：

  Protecting Groups for Thiols Suitable for Suzuki Conditions

  摘要：

  The thiol group is one of the few groups NOT tolerated by the Suzuki reaction. Therefore, a new protective group, the 2-methoxyisobutyryl group, was developed by tuning the electronic/steric properties of the acyl residue. Other thioesters, such as thioacetate, result in a more or less dominant side reaction, which to date has not been described: sulfur-assisted acylation of boronic acids. The reaction pathway for this new reaction is discussed.

  DOI：

  10.1021/ol0058902
• 作为产物：
  描述：

  2-methoxy-2-methylpropanoyl chloride 、 4-溴苯硫酚 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 40.25h， 以49%的产率得到2-Methoxy-2-methyl-thiopropionic acid S-(4-bromo-phenyl) ester
  参考文献：
  名称：

  Protecting Groups for Thiols Suitable for Suzuki Conditions

  摘要：

  The thiol group is one of the few groups NOT tolerated by the Suzuki reaction. Therefore, a new protective group, the 2-methoxyisobutyryl group, was developed by tuning the electronic/steric properties of the acyl residue. Other thioesters, such as thioacetate, result in a more or less dominant side reaction, which to date has not been described: sulfur-assisted acylation of boronic acids. The reaction pathway for this new reaction is discussed.

  DOI：

  10.1021/ol0058902

文献信息

• Protecting Groups for Thiols Suitable for Suzuki Conditions
  作者：Björn Zeysing、Carola Gosch、Andreas Terfort

  DOI：10.1021/ol0058902

  日期：2000.6.1

  The thiol group is one of the few groups NOT tolerated by the Suzuki reaction. Therefore, a new protective group, the 2-methoxyisobutyryl group, was developed by tuning the electronic/steric properties of the acyl residue. Other thioesters, such as thioacetate, result in a more or less dominant side reaction, which to date has not been described: sulfur-assisted acylation of boronic acids. The reaction pathway for this new reaction is discussed.