1-Diethoxyphosphoryl-1,1,2,2-tetrafluoro-2-iodoethane | 156628-95-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 1-Diethoxyphosphoryl-1,1,2,2-tetrafluoro-2-iodoethane
• CAS: 156628-95-4
• 化学式: C₆H₁₀F₄IO₃P
• 分子量: 364.015
• InChiKey: SSVVESAZHKDNQY-UHFFFAOYSA-N

物化性质

• 沸点：
  228.7±40.0 °C(Predicted)
• 密度：
  1.774±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-Diethoxyphosphoryl-1,1,2,2-tetrafluoro-2-iodoethane 在 bis(triphenylphosphine)nickel(II) chloride 、 四乙基碘化铵 、 锌 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 [4-(Diethoxy-phosphoryl)-1,1,2,2,3,3,4,4-octafluoro-butyl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  Synthesis of Novel Fluorinated Bisphosphonates and Bisphosphonic Acids

  摘要：

  The synthesis of novel fluorinated bisphosphonates with two, three, four, and six difluoromethylene groups (1a, 1b, 8, 12, and 15) (44-78%) by different approaches is described. The bisphosphonates were converted to the corresponding trimethylsilyl esters which on treatment with deionized water afforded the respective bisphosphonic acids (6, 10, and 14) in good yields.

  DOI：

  10.1021/jo00088a021
• 作为产物：
  描述：

  在 三甲基乙酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 1-Diethoxyphosphoryl-1,1,2,2-tetrafluoro-2-iodoethane
  参考文献：
  名称：

  Facile Synthesis of Fluorinated Phosphonates via Photochemical and Thermal Reactions

  摘要：

  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.

  DOI：

  10.1021/ja971345t

文献信息

• Nair; Burton, Journal of the American Chemical Society, 1994, vol. 116, # 13, p. 6041 - 6042
  作者：Nair、Burton

  DOI：——

  日期：——
• A new synthetic route to perfluoroalkylidene-α,ω-bisphosphonates
  作者：Haridasan K. Nair、Donald J. Burton

  DOI：10.1016/0040-4039(94)02266-e

  日期：1995.1

  The UV irradiation of a mixture of (EtO)(2)POP(OEt)(2) and I(CF2)(n)I (n = 3,4, 6) or I(CF2)(n)P(O)(OEt)(2) (n = 1, 2) results in the corresponding bisphosphonites or mixed phosphonite-phosphonates, respectively: which on oxidation by Me(3)COOH afforded the perfluoroalkylidene-alpha,omega-bisphosphonates in 64-77% isolated yields.
• Nair Haridasan K., Guneratne Ranil D., Modak Anil S., Burton Donald J., J. Org. Chem, 59 (1994) N 9, S 2393- 2398
  作者：Nair Haridasan K., Guneratne Ranil D., Modak Anil S., Burton Donald J.

  DOI：——

  日期：——
• Nair H. K., Burton D. J., J. Amer. Chem. Soc, 116 (1994) N 13, S 6041-6042
  作者：Nair H. K., Burton D. J.

  DOI：——

  日期：——
• 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.