diethyl perfluoro-n-hexylphosphonate | 79668-43-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: diethyl perfluoro-n-hexylphosphonate
• 英文别名: 1-Diethoxyphosphoryl-1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane
• CAS: 79668-43-2
• 化学式: C₁₀H₁₀F₁₃O₃P
• 分子量: 456.141
• InChiKey: QMNAFMXDSMIWLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  9
• 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：
  16

反应信息

• 作为产物：
  描述：

  diethyl perfluoro-n-hexylphosphonite 在 叔丁基过氧化氢 作用下， 以 甲醇 、 1,1,2-三氯三氟乙烷（CFC-113） 为溶剂， 生成 diethyl perfluoro-n-hexylphosphonate
  参考文献：
  名称：

  一种新的合成全氟烷基膦酸酯的方法，涉及CF-P键的轻松形成

  摘要：

  据报道，一种新的合成全氟烷基膦酸酯的方法涉及到CF-P键的容易形成。

  DOI：

  10.1039/c39810001173

文献信息

• A new synthetic route to perfluoroalkylphosphonates involving facile formation of the CF–P linkage
  作者：Masao Kato、Masaaki Yamabe

  DOI：10.1039/c39810001173

  日期：——

  A new synthetic route to perfluoroalkylphos-phonates which involves the facile formation of CF–P bonds is reported.

  据报道，一种新的合成全氟烷基膦酸酯的方法涉及到CF-P键的容易形成。
• A New synthesis of perfluoroalkanephosphonates
  作者：Wenbiao Cen、Yanchang Shen

  DOI：10.1016/s0022-1139(00)80351-6

  日期：1991.5

  A new method for the synthesis of perfluoroalkanephosphonates, R(f)-P(O)(OC2H5)2 has been developed, involving the facile formation of R(f)-P bond by the reaction of perfluoroalkyl Grignard reagents with diethyl chlorophosphate.
• KATO, MASAO;YAMABE, MASAAKI, J. CHEM. SOC. CHEM. COMMUN., 1981, N 22, 1173-1174
  作者：KATO, MASAO、YAMABE, MASAAKI

  DOI：——

  日期：——
• KATO, MASAO;AKIYAMA, KATSUYUKI;AKATSUKA, YONEZOH;YAMABE, MASAAKE, REPTS RES. LAB., ASAHI GLASS CO., 1982, 32, N 2, 117-128
  作者：KATO, MASAO、AKIYAMA, KATSUYUKI、AKATSUKA, YONEZOH、YAMABE, MASAAKE

  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.