3-pentafluorosulfanylprop-2-enyl acetate | 1046116-73-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-pentafluorosulfanylprop-2-enyl acetate
• 英文别名: 3-(Pentafluoro-lambda6-sulfanyl)prop-2-enyl acetate；3-(pentafluoro-λ6-sulfanyl)prop-2-enyl acetate
• CAS: 1046116-73-7
• 化学式: C₅H₇F₅O₂S
• 分子量: 226.167
• InChiKey: HNIWRLACYSOOTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  27.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-pentafluorosulfanylprop-2-enyl acetate 、 N-(1-ethoxy-1-oxoethylidene)-1-phenylmethanamine oxide 以 neat (no solvent) 为溶剂， 反应 5.0h， 以23%的产率得到(±)-[2-benzyl-3-(ethoxycarbonyl)-4-(pentafluorosulfanyl)isoxazolidin-5-yl]methyl acetate
  参考文献：
  名称：

  Synthesis of SF5-substituted isoxazolidines using 1,3-dipolar cycloaddition reactions of nitrones with pentafluorosulfanyl acrylic esters and amides

  摘要：

  1,3-Dipolar cycloadditions of nitrones with pentafluorosulfanyl-substituted acrylic ester and amides afforded new trisubstituted pentafluorosulfanylated isoxazolidines in moderate yields as 4-SF5-regioisomers. Theoretical calculations were carried out and the regioselectivity could be explained by the fact that the 5-SF5-regioisomer probably undertook a spontaneous degradation in the reaction medium via the loss of pentafluorosulfanyl anion. Diastereoselectivity of the 1,3-dipolar cycloadditions was also assessed according to NMR and X-ray diffraction analysis. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.08.050
• 作为产物：
  描述：

  2-bromo-3-pentafluorosulfanylpropyl acetate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 苯 为溶剂， 反应 0.08h， 以91%的产率得到3-pentafluorosulfanylprop-2-enyl acetate
  参考文献：
  名称：

  Improved and facile addition reactions of pentafluorosulfanyl bromide

  摘要：

  A solution of SF(5)Br in CCl(3)F (0.5-1 M) Was utilized to effect the addition of pentafluorosulfanyl bromide (SF(5)Br) to olefins. The reaction of the SF5Br solution in the presence of triethylborane (0.1 equiv) With an olefin over 20 min at 0 degrees C gave pentafluorosulfanylated compound 2(a-f) in high yield (Table 2). An efficient route for the preparation of synthetically useful SF5-containing esters is also described. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.080