1,1'-{[3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene-1-diyl]bis(thio)}bis(2-methoxybenzene)

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,1'-{[3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene-1-diyl]bis(thio)}bis(2-methoxybenzene)
• 英文别名: 1-Methoxy-2-[3,3,3-trifluoro-1-(2-methoxyphenyl)sulfanyl-2-(trifluoromethyl)prop-1-enyl]sulfanylbenzene
• 化学式: C₁₈H₁₄F₆O₂S₂
• 分子量: 440.43
• InChiKey: LAFBYBQAROHODS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  69.1
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  全氟异丁烯 、 2-甲氧基苯硫酚 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以78%的产率得到1,1'-{[3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene-1-diyl]bis(thio)}bis(2-methoxybenzene)
  参考文献：
  名称：

  Ketene thioacetal derivatives from perfluoroisobutene (PFIB) and its 1,1-dichloro analogue

  摘要：

  Perfluoroisobutene (PW) underwent double vinylic substitution with aromatic thiols under aqueous and non-aqueous conditions to give several new ketene thioacetals. The 1,1-dichloro analogue of PFIB was synthesised as a less toxic alternative to PFIB. It was shown to react similarly to PFIB. Reaction of the 1,1-dichloro analogue with 2-aminobenzenethiol did not give a ketene thioacetal, but instead yielded a fluorinated benzothiazole. PFIB reacted with thiols in aqueous phosphate buffer (pH 7). L-Cysteine isopropyl ester, a thiol pretreatment that protects animals from the toxic effects of PFIB, combines with PFIB under these conditions to give a fluorinated thiazole adduct. The acute inhalation toxicity of PFIB is most likely attributable to its ability to act as a bis-alkylating agent towards biological nucleophiles, especially thiols, in the lung. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(98)00343-1

文献信息

• Fluoroalkene chemistry
  作者：Christopher M. Timperley、Matthew J. Waters、Jackie A. Greenall

  DOI：10.1016/j.jfluchem.2005.11.008

  日期：2006.2

  Reactions of perfluoroisobutene (PFIB), perfluoropropene (PFP) and chlorotrifluoroethene (CTFE) with benzenethiol and 2-methoxybenzenethiol in acetonitrile, with potassium carbonate as base, were compared. PFIB reacted with benzenethiol to give ketene thioacetal (CF3)2CC(SAr)2 and with 2-methoxybenzenethiol to give mono- and bis-vinyl species (CF3)2CCFSAr and (CF3)2CC(SAr)2. PFP reacted with both thiols

  比较了全氟异丁烯（PFIB），全氟丙烯（PFP）和三氟氯乙烯（CTFE）在乙腈中以碳酸钾为碱与苯硫醇和2-甲氧基苯硫醇的反应。PFIB与苯硫醇反应生成烯酮硫缩醛（CF 3）2 CC（SAr）2，与2-甲氧基苯硫醇反应生成单乙烯基和双乙烯基物质（CF 3）2 CCFSAr和（CF 3）2 CC（SAr）2。PFP与两种硫醇反应生成加成产物CF 3 CFHCF 2 SAr和乙烯基异构体CF 3 CFCFSAr（6：1 E / Z比率）。CTFE与几种甲氧基取代的芳硫醇反应，得到结构CFClHCF 2 SAr的加成产物。整个研究中使用的芳基硫醇模仿了生物硫醇。氟代烯烃的吸入毒性以PFIB> PFP> CTFE的顺序降低，并且与它们对模型硫醇的反应性相关，这支持了当前的观点，即其毒性与它们与生物硫醇的反应能力有关。