1-甲氧基-4-(2,2,2-三氟-1-碘乙基)苯 | 104395-41-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-甲氧基-4-(2,2,2-三氟-1-碘乙基)苯
• 英文名称: 1-(4-Methoxyphenyl)-2,2,2-trifluoroethyl iodide
• 英文别名: 1-Methoxy-4-(2,2,2-trifluoro-1-iodoethyl)benzene；1-methoxy-4-(2,2,2-trifluoro-1-iodoethyl)benzene
• CAS: 104395-41-7
• 化学式: C₉H₈F₃IO
• 分子量: 316.062
• InChiKey: LWQSCLMERWNLHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-甲氧基-4-(2,2,2-三氟-1-碘乙基)苯 在 sodium perchlorate 、 水 作用下， 生成 2,2,2-三氟-1-(4-甲氧基苯基)乙醇
  参考文献：
  名称：

  On the importance of reactions of carbocation ion pairs in water: common ion inhibition of solvolysis of 1-(4-methoxyphenyl)-2,2,2-trifluoroethyl bromide and trapping of an ion-pair intermediate by solvent

  摘要：

  The effect of added bromide ion on the reactivity of 1-(4-methoxyphenyl)-2,2,2-trifluoroethyl bromide in water at 25-degrees-C and I = 6.00 (NaClO4) has been determined. The pseudo-first-order rate constant for this reaction decreases 300-fold as [NaBr] is increased from 0-5.00 M, which shows that greater-than-or-equal-to 99.7% of the solvolysis reaction proceeds through the free carbocation intermediate, whose concentration is reduced by mass action of added bromide ion. At high [NaBr], the observed rate constants show a significant positive deviation from the rate law for a reaction in which solvolysis products are derived solely from capture of the free carbocation. This deviation is consistent with a second pathway for the formation of solvolysis products, by direct attack of solvent on an ion-pair intermediate. The limiting velocity through this pathway, approached at high concentrations of bromide ion, is estimated to be 0.06% of that through the liberated carbocation. It is concluded that the capture of ion-pair intermediates of solvolysis reactions by solvent water is normally an unimportant reaction.

  DOI：

  10.1021/jo00028a041
• 作为产物：
  描述：

  2,2,2-三氟-1-(4-甲氧基苯基)乙醇 在 sodium iodide 作用下， 以 various solvent(s) 为溶剂， 反应 0.17h， 生成 1-甲氧基-4-(2,2,2-三氟-1-碘乙基)苯
  参考文献：
  名称：

  The extraordinarily long lifetimes and other properties of highly destabilized ring-substituted 1-phenyl-2,2,2-trifluoroethyl carbocations

  摘要：

  DOI：

  10.1021/ja00186a047

文献信息

• Richard, John P.; Yeary, Paul E., Journal of the American Chemical Society, 1993, vol. 115, # 5, p. 1739 - 1744
  作者：Richard, John P.、Yeary, Paul E.

  DOI：——

  日期：——
• The extraordinarily long lifetimes and other properties of highly destabilized ring-substituted 1-phenyl-2,2,2-trifluoroethyl carbocations
  作者：John P. Richard

  DOI：10.1021/ja00186a047

  日期：1989.2
• On the importance of reactions of carbocation ion pairs in water: common ion inhibition of solvolysis of 1-(4-methoxyphenyl)-2,2,2-trifluoroethyl bromide and trapping of an ion-pair intermediate by solvent
  作者：John P. Richard

  DOI：10.1021/jo00028a041

  日期：1992.1

  The effect of added bromide ion on the reactivity of 1-(4-methoxyphenyl)-2,2,2-trifluoroethyl bromide in water at 25-degrees-C and I = 6.00 (NaClO4) has been determined. The pseudo-first-order rate constant for this reaction decreases 300-fold as [NaBr] is increased from 0-5.00 M, which shows that greater-than-or-equal-to 99.7% of the solvolysis reaction proceeds through the free carbocation intermediate, whose concentration is reduced by mass action of added bromide ion. At high [NaBr], the observed rate constants show a significant positive deviation from the rate law for a reaction in which solvolysis products are derived solely from capture of the free carbocation. This deviation is consistent with a second pathway for the formation of solvolysis products, by direct attack of solvent on an ion-pair intermediate. The limiting velocity through this pathway, approached at high concentrations of bromide ion, is estimated to be 0.06% of that through the liberated carbocation. It is concluded that the capture of ion-pair intermediates of solvolysis reactions by solvent water is normally an unimportant reaction.