1-(2-溴-1,1,1-三氟丙烷-2-基)-4-甲氧基苯 | 76954-04-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-(2-溴-1,1,1-三氟丙烷-2-基)-4-甲氧基苯
• 英文名称: 1-(4-Methoxyphenyl)-1-(trifluoromethyl)ethyl bromide
• 英文别名: 1-(2-Bromo-1,1,1-trifluoropropan-2-yl)-4-methoxybenzene
• CAS: 76954-04-6
• 化学式: C₁₀H₁₀BrF₃O
• 分子量: 283.088
• InChiKey: LKGMKELBRSFBNB-UHFFFAOYSA-N

物化性质

• 沸点：
  238.9±40.0 °C(Predicted)
• 密度：
  1.465±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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-(2-溴-1,1,1-三氟丙烷-2-基)-4-甲氧基苯 、 1-methoxy-4-(2,2,2-trifluoroethyl)benzene 生成 4-methoxy-(2,2,2-trifluoro-1-methylethyl)benzene
  参考文献：
  名称：

  Substituted benzylaminopiperidine compounds

  摘要：

  这项发明提供了一种取代苄基氨基哌啶化合物，可用于治疗胃肠道疾病；中枢神经系统（CNS）疾病；炎症性疾病；呕吐；尿失禁；疼痛；偏头痛；晒伤；由幽门螺杆菌引起的疾病、疾病和不良症状；或血管生成，尤其是在哺乳动物主体中的中枢神经系统疾病，尤其是在人类中。

  公开号：

  US06329396B1
• 作为产物：
  描述：

  2,2,2-三氟-4-甲氧基乙酰苯 在 三溴化磷 作用下， 反应 4.0h， 生成 1-(2-溴-1,1,1-三氟丙烷-2-基)-4-甲氧基苯
  参考文献：
  名称：

  替代效应。十九。1-Aryl-1-(trifluoromethyl)ethyl Tosylates 的溶剂分解

  摘要：

  1-芳基-1-（三氟甲基）乙基甲苯磺酸酯的溶剂分解速率在 80% 乙醇水溶液中测定一系列取代基。Brown ρ+σ+ 处理未能给出简单的线性图，但所有 p-π-供体都从元相关线向上偏离。另一方面，Yukawa-Tsuno LArSR Eq。在整个取代基范围内给出线性相关性，log(k⁄k0)=−6.287(σ°+1.388Δ\barσR+)，具有出色的精度。α-CF3 对碳正离子中间体的强烈不稳定似乎仅反映在极高的 r 值上，而不反映在取代基效应的 ρ 值上。这与文献中基于简单布朗 σ+ 处理给出的该反应的结论严重冲突。该反应具有极高的共振需求 r=1.4，应该远远超出简单的 Brown σ+ 分析的范围。改变共振需求应该是充分描述关于共轭碳正离子反应的取代基效应的基本要求。

  DOI：

  10.1246/bcsj.63.1129

文献信息

• Solvolysis of 1-aryl-1-(trifloromethyl)ethyl tosylates. Evidence for an extremely high electron demand carbenium ion intermediate due to the presence of α-trifluoromethyl substituent
  作者：Kwang-Ting Liu、Ching-Fen Sheu

  DOI：10.1016/0040-4039(80)88074-9

  日期：1980.1

  The rate-retarding effect of ?-trifluoromethyl group observed in the solvolysis of 1-aryl-1-(trifluoromethyl)ethyl tosylates is so profound that a very large negative α+ value, −8.82, is resulted and the 1-phenyl derivative becomes even less reactive than benzyl tosylate.

  在1-芳基-1-（三氟甲基）乙基甲苯磺酸酯的溶剂分解中观察到的α-三氟甲基的缓速作用如此深刻，以至于产生非常大的负α +值-8.82，并且1-苯基衍生物变成甚至不如甲苯磺酸苄酯。
• The effects of .alpha.-substituents on the kinetic and thermodynamic stability of 4-methoxybenzyl carbocations: carbocation lifetimes that are independent of their thermodynamic stability
  作者：Tina L. Amyes、Ishmael W. Stevens、John P. Richard

  DOI：10.1021/jo00074a036

  日期：1993.10

  The following new rate constants for reaction of alpha-substituted 4-methoxybenzyl carbocations, 4-MeOC6H4CR1(R2)+, With a solvent of 50:50 (v/v) trifluoroethanol/water at 25-degrees-C and ionic strength 0.50 (NaClO4) are reported: 4-MeOC6H4CH(OMe)+, k(S) = 2.2 X 10(7) s-1; 4-MeOC6H4CH(N3)+, k(S) = 3.3 X 10(5) s-1; 4-MeOC6H4C(CH3)2+, k(S) = 1.3 x 10(7) s-1; 4-MeOC6H4CH(CO2Et)+, k(S) = 1.4 X 10(7) s-1; 4-MeOC6H4CCH3(CF3)+, k(S) = 2.5 x 10(7) s-1. The values of k(S) for reaction of 4-MeOC6H4CR1(R2)+ with 50:50 (v/v) trifluoroethanol/water are nearly independent of very large changes in the thermodynamic stability of these carbocations caused by the addition of a wide range of electron-withdrawing or electron-donating groups at the alpha-position. In the most extreme case, the change from an alpha-methoxy to two alpha-(trifluoromethyl) substituents leads to a 23 kcal/mol thermodynamic destabilization of 4-MeOCrH4CR1(R2)+ relative to the neutral azide ion adducts but a 5-fold decrease in its reactivity toward solvent. The data show that the effects of alpha-substituents on the kinetic stability of 4-MeOC6H4CR1(R2)+ are complex and do not parallel the thermodynamic stability of these carbocations. The results are explained by consideration of the polar and resonance effects of the alpha-substituents on both the thermodynamic driving force and the intrinsic barrier for capture of the carbocations by solvent. These reactions are a new example of the consequences of the ''principle of nonperfect synchronization''.41
• Solvolytic studies of the highly deactivated 1-aryl-1-(trifluoromethyl)ethyl tosylates
  作者：Kwang Ting Liu、Mann Yan Kuo、Ching Fen Sheu

  DOI：10.1021/ja00365a038

  日期：1982.1
• LIU, KWANG-TING;WU, YUH, WERN, J. CHEM. RES. SYNOP., 1984, N 12, 408-409
  作者：LIU, KWANG-TING、WU, YUH, WERN

  DOI：——

  日期：——