3-(4-allyloxyphenyl)-2-methyl-isoxazolidine-4-sulfonic acid pentafluorophenyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-(4-allyloxyphenyl)-2-methyl-isoxazolidine-4-sulfonic acid pentafluorophenyl ester
• 英文别名: (2,3,4,5,6-pentafluorophenyl) (3S,4S)-2-methyl-3-(4-prop-2-enoxyphenyl)-1,2-oxazolidine-4-sulfonate
• 化学式: C₁₉H₁₆F₅NO₅S
• 分子量: 465.398
• InChiKey: MCUSSJXEZAMUND-XIKOKIGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  73.4
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3-(4-allyloxyphenyl)-2-methyl-isoxazolidine-4-sulfonic acid pentafluorophenyl ester 在 hexacarbonyl molybdenum 作用下， 以 水 、 乙腈 为溶剂， 反应 16.0h， 以52%的产率得到[3-(4-allyloxy-phenyl)-2-methyl-1,1-dioxo-1λ⁶-[1,2]thiazetidin-4-yl]-methanol
  参考文献：
  名称：

  New Synthesis of β-Sultams from Pentafluorophenyl Sulfonates

  摘要：

  A stereoselective one-pot synthesis of substituted 1,2-thiazetidine 1,1-dioxides (beta-sultams) has been achieved from heterocyclic pentafluorophenyl (PFP) sulfonates. Mild N-O bond cleavage of isoxazolidines followed by intramolecular cyclization of the amine onto the PFP demonstrates the potential utility for using the PFP sulfonate as a valuable precursor to sulfonamides.

  DOI：

  10.1021/ol062164b
• 作为产物：
  描述：

  4-烯丙氧基苯甲醛 在 盐酸 、 碳酸氢钠 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 3-(4-allyloxyphenyl)-2-methyl-isoxazolidine-4-sulfonic acid pentafluorophenyl ester
  参考文献：
  名称：

  Synthesis of Functionalized Sulfonamides via 1,3-Dipolar Cycloaddition of Pentafluorophenyl Vinylsulfonate

  摘要：

  [GRAPHICS]An efficient intermolecular 1,3-dipolar cycloaddition of a variety of nitrones to pentafluorophenyl (PFP) vinylsulfonate is described. The transformation produces stable "reversed" cycloadducts of unprecedented stereo- and regioselectivity. Subsequent amine displacement of the PFP moiety furnished functionalized sulfonamide products in good yields.

  DOI：

  10.1021/ol0347388

文献信息

• Synthesis of Functionalized Sulfonamides via 1,3-Dipolar Cycloaddition of Pentafluorophenyl Vinylsulfonate
  作者：Stephen Caddick、Hannah D. Bush

  DOI：10.1021/ol0347388

  日期：2003.7.1

  [GRAPHICS]An efficient intermolecular 1,3-dipolar cycloaddition of a variety of nitrones to pentafluorophenyl (PFP) vinylsulfonate is described. The transformation produces stable "reversed" cycloadducts of unprecedented stereo- and regioselectivity. Subsequent amine displacement of the PFP moiety furnished functionalized sulfonamide products in good yields.
• New Synthesis of β-Sultams from Pentafluorophenyl Sulfonates
  作者：Alexandra K. de K. Lewis、B. James Mok、Derek A. Tocher、Jonathan D. Wilden、Stephen Caddick

  DOI：10.1021/ol062164b

  日期：2006.11.1

  A stereoselective one-pot synthesis of substituted 1,2-thiazetidine 1,1-dioxides (beta-sultams) has been achieved from heterocyclic pentafluorophenyl (PFP) sulfonates. Mild N-O bond cleavage of isoxazolidines followed by intramolecular cyclization of the amine onto the PFP demonstrates the potential utility for using the PFP sulfonate as a valuable precursor to sulfonamides.