bis(pentafluorophenyl)methyl chloride | 5736-48-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis(pentafluorophenyl)methyl chloride
• 英文别名: Bis(pentafluorophenyl)chloromethane；Bis-(pentafluorphenyl)-chlormethan；Bis(pentafluorphenyl)chlormethan；Chlor-bis-pentafluorphenyl-ethan；1-[chloro-(2,3,4,5,6-pentafluorophenyl)methyl]-2,3,4,5,6-pentafluorobenzene
• CAS: 5736-48-1
• 化学式: C₁₃HClF₁₀
• 分子量: 382.588
• InChiKey: FFVRKKQHIAGSGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  bis(pentafluorophenyl)methyl chloride 在 silver tetrafluoroborate 、 potassium tert-butylate 、 sodium nitrite 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 环己烷 、 乙酸酐 、 溶剂黄146 为溶剂， 反应 2.02h， 生成 1,1',1'',1'''-(1,1,2,2-乙烷四基)四(五氟苯)
  参考文献：
  名称：

  Generation, reactions, direct observation, and kinetics of decafluorodiphenylcarbene

  摘要：

  Bis(pentafluorophenyl)diazomethane (1a) was prepared, and reactivities of perfluorodiphenylcarbene (2a) generated by photolysis of la were investigated not only in terms of product analysis but also by using matrix isolation spectroscopy as well as laser flash photolysis techniques. Product distributions observed in the reactions of 2a in benzene, cyclohexane, and trans-1,2-dichloroethylene suggested that 2a reacted with those substrates with moderate reactivities toward carbene mostly in its singlet state presumably owing to the increased electrophilicity induced by fluorine substituents while the reaction with the alkane C-H bonds in concerted fashion was retarded partly due to steric effect in the singlet state which thus decayed to the triplet states that underwent predominantly H atom abstraction forming tetraarylethane. Photolysis of 1a in Ar matrix at 10 K produced 2a which was observed by IR and UV and shown to react with doped O2 to produce ultimately perfluorobenzoate by way of the carbonyl oxide and dioxirane, both intermediates being characterized by IR and UV/vis spectroscopy. Laser flash photolysis of 1a in acetonitrile solution produced a transient absorption (lambda = 320 nm) due to bis(pentafluorophenyl)methyl radical (14a) obviously produced by H atom abstraction of the triplet 2a, which was trapped by oxygen to generate the carbonyl oxide (11a) showing its absorption maximum at 400 nm (tau = 5 ms) and also by 1,4-cyclohexadiene to form the methyl radical (14a) with the rate constant of 1.1 x 10(7) M-1 s-1. The lifetime of the triplet 2a was estimated to be approximately 1 us.

  DOI：

  10.1021/jo00077a040
• 作为产物：
  描述：

  十氟二苯甲醇 在 五氯化磷 作用下， 以 四氯化碳 为溶剂， 反应 4.0h， 以81%的产率得到bis(pentafluorophenyl)methyl chloride
  参考文献：
  名称：

  H 2被高度缺电子的芳烷基化有机硼烷激活†

  摘要：

  合成并综合表征了缺电子且空间庞大的三烷基硼烷衍生物三[双（五氟苯基）甲基]硼烷[ 1，B（CH（C 6 F 5）2）3 ]。1 H和19 F NMR的详细研究揭示了溶液相中的两个动态键旋转过程。尽管常规探针（Gutmann–Beckett和Childs方法）暗示该化合物的路易斯酸度非常有限，但仍可用于生成能够在醚溶液中杂化活化H 2的失意的Lewis对，这表明1的亲水性可与强路易斯酸B（C6 F 5） 3。

  DOI：

  10.1039/c5dt00821b

文献信息

• Anichkina,S.A. et al., Journal of general chemistry of the USSR, 1968, vol. 38, p. 2409 - 2412
  作者：Anichkina,S.A. et al.

  DOI：——

  日期：——
• Vorozhtsov,N.N. et al., Doklady Chemistry, 1966, vol. 166, p. 107 - 110
  作者：Vorozhtsov,N.N. et al.

  DOI：——

  日期：——
• Vlasov,V.M.; Yakobson,G.G., Journal of Organic Chemistry USSR (English Translation), 1976, vol. 12, p. 249 - 258
  作者：Vlasov,V.M.、Yakobson,G.G.

  DOI：——

  日期：——
• Tomioka Hideo, Mizutani Kenzoh, Matsumoto Kenji, Hirai Katauyuki, J. Org. Chem, 58 (1993) N 25, S 7128-7134
  作者：Tomioka Hideo, Mizutani Kenzoh, Matsumoto Kenji, Hirai Katauyuki

  DOI：——

  日期：——