9-Phenanthrenol, 1,3,4-trimethyl-10-(2,4,6-trimethylphenyl)- | 185553-11-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 9-Phenanthrenol, 1,3,4-trimethyl-10-(2,4,6-trimethylphenyl)-
• 英文别名: 1,3,4-trimethyl-10-(2,4,6-trimethylphenyl)phenanthren-9-ol
• CAS: 185553-11-1
• 化学式: C₂₆H₂₆O
• 分子量: 354.492
• InChiKey: NKGMZQMMYLMUPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-苯基-2,2-二(2,4,6-三甲基苯基)乙烯醇 在 吡啶 、 tris(4-nitrophenyl)aminium hexachloroantimonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 9-Phenanthrenol, 1,3,4-trimethyl-10-(2,4,6-trimethylphenyl)-
  参考文献：
  名称：

  Electroactive protecting groups and reaction units. Part 4. Mesolytic O–CO bond cleavage versus intramolecular cyclization reaction in enol trifluoroacetate cation radicals. A kinetic and mechanistic investigation

  摘要：

  The one-electron oxidation of two beta,beta-dimesityl enol trifluoroacetates with different substituents R at C-alpha was investigated. For the first time enol trifluoroacetate cation radicals could be reversibly monitored in cyclic voltammetry experiments allowing the determination of the rate constants of their follow-up reactions. While mesolytic cleavage of the O-CO bond (k(f) = 1.4 s(-1)) with direct formation of an alpha-carbonyl cation constitutes the primary reaction of the enol trifluoroacetate cation radical with R = Bu(t), the one with R = Ph exclusively cyclizes (k(f) = 75 s(-1)) to a phenanthrene derivative. This change in reactivity can be rationalized by the different nature of the electrophoric system as a function of the substituent R.

  DOI：

  10.1039/p29960002401

文献信息

• Electroactive protecting groups and reaction units. Part 4. Mesolytic O–CO bond cleavage versus intramolecular cyclization reaction in enol trifluoroacetate cation radicals. A kinetic and mechanistic investigation
  作者：Michael Schmittel、Holger Trenkle

  DOI：10.1039/p29960002401

  日期：——

  The one-electron oxidation of two beta,beta-dimesityl enol trifluoroacetates with different substituents R at C-alpha was investigated. For the first time enol trifluoroacetate cation radicals could be reversibly monitored in cyclic voltammetry experiments allowing the determination of the rate constants of their follow-up reactions. While mesolytic cleavage of the O-CO bond (k(f) = 1.4 s(-1)) with direct formation of an alpha-carbonyl cation constitutes the primary reaction of the enol trifluoroacetate cation radical with R = Bu(t), the one with R = Ph exclusively cyclizes (k(f) = 75 s(-1)) to a phenanthrene derivative. This change in reactivity can be rationalized by the different nature of the electrophoric system as a function of the substituent R.