1-(4-Methoxyphenyl)-2,2,2-trifluoroethyl azide | 150935-07-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-Methoxyphenyl)-2,2,2-trifluoroethyl azide
• 英文别名: 1-(1-Azido-2,2,2-trifluoroethyl)-4-methoxybenzene
• CAS: 150935-07-2
• 化学式: C₉H₈F₃N₃O
• 分子量: 231.177
• InChiKey: VTSJOJZIBHFITJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(4-Methoxyphenyl)-2,2,2-trifluoroethyl azide 以 水 为溶剂， 生成 2,2,2-Trifluoro-1-(4-methoxyphenyl)ethylium
  参考文献：
  名称：

  Carbocation lifetimes that are independent of carbocation stability: the reaction of α-substituted 4-methoxybenzyl carbocations

  摘要：

  α-甲氧基-4-甲氧基苄基碳正离子与溶剂三氟乙醇→水（50：50 v/v）反应，速率常数ks= 3 × 107 s→1；当碳正离子通过强吸电子α-CF3 取代基取代强给电子α-OMe 取代基而不稳定时，ks 增加不到两倍。

  DOI：

  10.1039/c39910000200
• 作为产物：
  描述：

  1-(1-溴-2,2,2-三氟乙基)-4-甲氧基苯 在 sodium azide 、 水 作用下， 生成 1-(4-Methoxyphenyl)-2,2,2-trifluoroethyl azide
  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

文献信息

• 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
• 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：——