(N,N-diisopropylcarbamoyloxy)methyl p-tolyl sulfone | 1401336-41-1

• 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: (N,N-diisopropylcarbamoyloxy)methyl p-tolyl sulfone
• 英文别名: (4-methylphenyl)sulfonylmethyl N,N-di(propan-2-yl)carbamate
• CAS: 1401336-41-1
• 化学式: C₁₅H₂₃NO₄S
• 分子量: 313.418
• InChiKey: RRYCSRNYLCCQPO-UHFFFAOYSA-N

物化性质

• 沸点：
  441.8±38.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 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：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (N,N-diisopropylcarbamoyloxy)methyl p-tolyl sulfone 、 邻甲氧基苯甲醛 在 正丁基锂 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.58h， 以68%的产率得到1-O-(N,N-diisopropylcarbamoyl)-1-(2-methoxyphenyl)-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：

  4-甲苯硫酚 在 sodium methylate 、 N,N-二甲基苯胺 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (N,N-diisopropylcarbamoyloxy)methyl p-tolyl sulfone
  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

文献信息

• (N,N-Diisopropylcarbamoyloxy)-methyl p-tolyl sulfone: preparation and application for the syntheses of 1,2-diols
  作者：Lu Ma、Dongmei Zhao、Lin Chen、Xin Wang、Yue-Lei Chen、Jingkang Shen

  DOI：10.1016/j.tet.2012.08.025

  日期：2012.10

  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.