1,1,2,2,3,3,4,4-Octafluoro-4-iodobutane-1-sulfonyl fluoride | 146829-77-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 磺酰卤
• 英文名称: 1,1,2,2,3,3,4,4-Octafluoro-4-iodobutane-1-sulfonyl fluoride
• CAS: 146829-77-8
• 化学式: C₄F₉IO₂S
• 分子量: 409.999
• InChiKey: BAZJGQDNKLKFRW-UHFFFAOYSA-N

物化性质

• 沸点：
  126.3±40.0 °C(Predicted)
• 密度：
  2.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  diethyl allyloxymethylphosphonate 、 1,1,2,2,3,3,4,4-Octafluoro-4-iodobutane-1-sulfonyl fluoride 在 过氧化苯甲酰 作用下， 反应 1.0h， 以80%的产率得到(4,4,5,5,6,6,7,7-Octafluoro-7-fluorosulfonyl-2-iodo-heptyloxymethyl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  Synthesis of novel partially fluorinated phosphonic/sulfonic acids

  摘要：

  A new-synthesis of (EtO)2P(O)CH2OCH2CH = CH2 (1) has been developed. Addition of I(CF2)4SO2F or I(CF2)2O(CF2)2SO2F to 1 followed by hydrolysis, reduction and ion exchange of the addition adducts gave (HO)2P(O)CH2O(CH2)3(CF2)4SO3H.2H2O and (HO)2P-(O)CH2O(CH2)3(CF2)2O(CF2)2SO3H.3H2O, respectively.

  DOI：

  10.1016/s0022-1139(00)80100-1
• 作为产物：
  描述：

  3-iodoperfluorobutanesulfonyl chloride 在 potassium fluoride 作用下， 以 乙腈 为溶剂， 以83%的产率得到1,1,2,2,3,3,4,4-Octafluoro-4-iodobutane-1-sulfonyl fluoride
  参考文献：
  名称：

  A useful synthesis of ω-iodoperfluoroalkanesulfonyl fluorides and perfluoroalkane-α,ω-bis-sulfonyl fluorides

  摘要：

  Omega-iodoperfluoroalkanesulfonyl fluorides and perfluoroalkane-alpha,omega-bis-sulfonyl fluorides have been prepared via deiodosulfination, chlorination, and then chlorine-fluorine exchange reaction of alpha,omega-diiodoperfluoroalkanes I(CF2)nI (n=3, 4, 6). Similar reaction of I(CF2)2O(CF2)2SO2F affords FSO2(CF2)2O(CF2)2SO2F.

  DOI：

  10.1016/s0022-1139(00)82200-9

文献信息

• Facile Synthesis of Fluorinated Phosphonates <i>via</i> Photochemical and Thermal Reactions
  作者：Haridasan K. Nair、Donald J. Burton

  DOI：10.1021/ja971345t

  日期：1997.10.1

  Under UV irradiation (254 nm) at ambient temperature, a degassed mixture of (EtO)(2)POP(OEt)(2) and RfI R-f=CF3, C2F5, C4F9, C6F13, (CF3)(2)CF, CF2CF=CF2, ClCF2CF2, BrCF2CF2, C6F5, ClCF2CFClCF2CF2, I(CF2)(3), I(CF2)(4), FO2S(CF2)(4), FO2S(CF2)(2)O(CF2)(2)} affords the fluorinated phosphonite, [RfP(OEt)(2)]. Oxidation of the phosphonites, [RfP(OEt)(2)], with Me3COOH gave the corresponding fluorinated phosphonates, (EtO)(2)P(O)R-f(1-14), in 35-80% isolated yields. CF3CCl2I reacts with (EtO)(2)POP(OEt)(2) at room temperature in the absence of UV irradiation to afford [CF3CCl2P(OEt)(2)] which upon oxidation gave a 52% yield of CF3CCl2P(O)(OEt)(2) (15). The reaction of (EtO)(2)POP(OEt)(2) and RfI (R-f=ClCF2CF2, BrCF2CF2, C2F5) at 125 degrees C in the presence of Me3COOCMe3 and subsequent oxidation of the resultant phosphonites afforded phosphonates (2, 7, and 8) albeit in lower yields (49-62%) compared to those of the photochemical reaction (58-80%). (RO)(2)P(O)CF2CF2I (R=Et, i-Pr) (16 and 17) was obtained (42-48%) when a degassed mixture of (RO)(3)P and BrCF2CF2I was subjected to UV irradiation (254 nm) at ambient temperature via a unique photochemical transformation.