<(2-hydroxy-3-tosyl)propyl>triphenylphosphonium bromide | 135908-10-0

• 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: <(2-hydroxy-3-tosyl)propyl>triphenylphosphonium bromide
• CAS: 135908-10-0
• 化学式: Br*C₂₈H₂₈O₃PS
• 分子量: 555.472
• InChiKey: RLPPVWMKUGACFG-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.13
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-(p-toluenesulfonylmethyl)oxirane 、 三苯基膦 以 various solvent(s) 为溶剂， 反应 4.0h， 以74%的产率得到<(2-hydroxy-3-tosyl)propyl>triphenylphosphonium bromide
  参考文献：
  名称：

  β,γ-efoxy sulfones in organic synthesis. Part 2: Preparation of β,γ-bifunctionalized sulfones

  摘要：

  Heteronucleophiles reagents react with beta,gamma-epoxy sulfones 1 at the gamma-position in the presence of Ti(OPr(i))4 or magnesium halides to afford regioselectively gamma-functionalized beta-hydroxy sulfones 2. With soft nucleofiles such as sodium azide, triphenylphosphine, or sodium benzethiolate the reaction takes place in the absence of Lewis acids. In the case of basic reagents such as sodium methoxide or diethylamine the corresponding regioisomers, the beta-functionalized gamma-hydroxy sulfones 3 were exclusively obtained. The preparation of compounds 3 (R2 = H) was also carried out starting from 3-tosyl-2-propen-1-ol (4) by Micheal addition of different heteronucleophiles.

  DOI：

  10.1016/s0040-4020(01)87131-3

文献信息

• β,γ-efoxy sulfones in organic synthesis. Part 2: Preparation of β,γ-bifunctionalized sulfones
  作者：Carmen Nájera、José M. Sansano

  DOI：10.1016/s0040-4020(01)87131-3

  日期：1991.1

  Heteronucleophiles reagents react with beta,gamma-epoxy sulfones 1 at the gamma-position in the presence of Ti(OPr(i))4 or magnesium halides to afford regioselectively gamma-functionalized beta-hydroxy sulfones 2. With soft nucleofiles such as sodium azide, triphenylphosphine, or sodium benzethiolate the reaction takes place in the absence of Lewis acids. In the case of basic reagents such as sodium methoxide or diethylamine the corresponding regioisomers, the beta-functionalized gamma-hydroxy sulfones 3 were exclusively obtained. The preparation of compounds 3 (R2 = H) was also carried out starting from 3-tosyl-2-propen-1-ol (4) by Micheal addition of different heteronucleophiles.