1-(2-Chloro-4,4-dimethylpentan-2-yl)-3-(trifluoromethyl)benzene | 223128-59-4

• 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: 1-(2-Chloro-4,4-dimethylpentan-2-yl)-3-(trifluoromethyl)benzene
• CAS: 223128-59-4
• 化学式: C₁₄H₁₈ClF₃
• 分子量: 278.745
• InChiKey: BVRZSWBFLBFORX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  m-trifluoro-methyl-phenyl-magnesium bromide 在 盐酸 、 potassium hydrogensulfate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 1-(2-Chloro-4,4-dimethylpentan-2-yl)-3-(trifluoromethyl)benzene
  参考文献：
  名称：

  Solvolysis of 2-Aryl-2-chloro-4,4-dimethylpentanes. Confirmation of Validity of Brown−Okamoto σ⁺ Constants

  摘要：

  Specific rate constants of solvolysis in 90% aqueous acetone have been determined at 25 degrees C for 10 2-aryl-2-chloro-4,4-dimethylpentanes (3) having a substituent p-cycPr, p-Me, m-Me, p-F, (H), p-Cl, m-Cl, m-CF3, p-CF3, or p-NO2. The Hammett-Brown relation is satisfactorily Linear (r = 0.999) with pi of -4.51, showing that Brown-Okamoto sigma(+) values based on the solvolysis of the cumyl chloride system 1 are widely usable for the substrates solvolyzing without appreciable nucleophilic solvent participation. Solvolysis of 3 having 3,5-Cl-2 or 3,5-(CF3)(2) substituents suggests the use of sigma(+) values of +0.740 and +0.982 instead of respective 2 sigma(m)(+) values of +0.798 and +1.040. The large negative rho(+) values in TFE of -5.91 and -5.63 for 1 and 3, respectively, reflect decreased nucleophilic (or Br phi nsted base type) solvation. Comparison of solvolysis rates of 1 with 3, both having m-Cl, p-CFB, or 3,5-(CF3)(2) substituents, in aqueous ethanol, aqueous acetone, TFE, and TFE-EtOH suggests that nucleophilic intervention by solvent in the cumyl system increases as the intermediate carbocation becomes more electron-demanding.

  DOI：

  10.1021/jo9821067