对甲苯基(N,N-二异丙基氨基甲酰氧基)甲基硫醚 | 1401336-40-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 对甲苯基(N,N-二异丙基氨基甲酰氧基)甲基硫醚
• 英文名称: p-tolyl (N,N-diisopropylcarbamoyloxy)methyl sulfide
• 英文别名: (4-methylphenyl)sulfanylmethyl N,N-di(propan-2-yl)carbamate
• CAS: 1401336-40-0
• 化学式: C₁₅H₂₃NO₂S
• 分子量: 281.419
• InChiKey: GWFOGFSSAOVHCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  对甲苯基(N,N-二异丙基氨基甲酰氧基)甲基硫醚 在 正丁基锂 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.08h， 生成 1-(4-fluorophenyl)-2-O-(N,N-diisopropylcarbamoyl)-1,2-ethanediol
  参考文献：
  名称：

  (N,N-Diisopropylcarbamoyloxy)-methyl p-tolyl sulfone: preparation and application for the syntheses of 1,2-diols

  摘要：

  1-(N,N-Diisopropylcarbamoyloxy)-1-tosyl-methane (CbOCH2Ts, Cb=N,N-diisopropylcarbamoyl) was readily prepared from p-ToISH, paraformaldehyde and CbCl. With the dual activation of CbO- and Ts-substitutions, deprotonation of CbOCH2Ts could be effected not only by n-BuLi, but also by Grignard reagents. Upon deprotonation, the title compound adds to various carbonyl structures. By choosing proper organometallic reagents for consecutive steps, the addition intermediate undergoes in situ conversions to efficiently yield regioselectively O-Cb protected and unprotected 1,2-diols. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.025
• 作为产物：
  描述：

  二异丙基甲胺酰氯 、 ((4-methylphenyl)thio)methanol 在 N,N-二甲基苯胺 作用下， 以 二氯甲烷 为溶剂， 以21.4 g的产率得到对甲苯基(N,N-二异丙基氨基甲酰氧基)甲基硫醚
  参考文献：
  名称：

  (N,N-Diisopropylcarbamoyloxy)-methyl p-tolyl sulfone: preparation and application for the syntheses of 1,2-diols

  摘要：

  1-(N,N-Diisopropylcarbamoyloxy)-1-tosyl-methane (CbOCH2Ts, Cb=N,N-diisopropylcarbamoyl) was readily prepared from p-ToISH, paraformaldehyde and CbCl. With the dual activation of CbO- and Ts-substitutions, deprotonation of CbOCH2Ts could be effected not only by n-BuLi, but also by Grignard reagents. Upon deprotonation, the title compound adds to various carbonyl structures. By choosing proper organometallic reagents for consecutive steps, the addition intermediate undergoes in situ conversions to efficiently yield regioselectively O-Cb protected and unprotected 1,2-diols. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.025