9-hydroxy-9-benzhydrylfluorene | 4709-67-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9-hydroxy-9-benzhydrylfluorene
• 英文别名: 9-benzhydryl-9H-fluoren-9-ol；9-oxy-9-benzhydryl-fluorene；9-Oxy-9-benzhydryl-fluoren；9-Benzhydryl-fluoren-9-ol；9-Benzhydryl-9H-fluoren-9-ol；9-benzhydrylfluoren-9-ol
• CAS: 4709-67-5
• 化学式: C₂₆H₂₀O
• 分子量: 348.444
• InChiKey: FGYYSTRNLCQWBN-UHFFFAOYSA-N

物化性质

• 熔点：
  183 °C
• 沸点：
  538.0±19.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-hydroxy-9-benzhydrylfluorene 在 氯磺酸 作用下， 以 二氯甲烷 为溶剂， 生成 9-Benzhydrylfluoren-9-ylium
  参考文献：
  名称：

  Studies of 9-Fluorenyl Carbocations. Intramolecular Hydride Migration in a Substituted 9-Fluorenyl Carbocation

  摘要：

  The substituted fluorenyl cation, 9-(diphenylmethyl)fluoren-9-yl cation (4), is formed under stable ion conditions (low temperature/strong acid) from its corresponding alcohol 3. This ion is transformed to a substituted diphenyl methyl cation 8 at ambient temperature via an apparent 1,2-hydrogen shift. Irradiation of 9-(diphenylmethyl)fluoren-9-ol in methanol gives products derived from the corresponding cation along with radical-derived products from C-C and C-O homolysis processes. The laser flash photolysis of this alcohol gave a transient corresponding to cation 4. All of the photoproducts are derived from cation 4 or radical pathways. High level MO calculations point to a high barrier (23.8 kcal mol(-1)) for the 1,2-hydride shift. This barrier is the consequence of the minimum energy conformation of this fluorenyl cation which is less than ideal for the periplanar geometry necessary for this process.

  DOI：

  10.1021/jo0009200
• 作为产物：
  描述：

  二苯基甲烷 生成 9-hydroxy-9-benzhydrylfluorene
  参考文献：
  名称：

  Schlenk; Bergmann, Justus Liebigs Annalen der Chemie, 1928, vol. 464, p. 28

  摘要：

  DOI：

文献信息

• Radical–radical cross coupling reactions of photo-excited fluorenones
  作者：Simmi Sharma、Shaista Sultan、Shekaraiah Devari、Bhahwal Ali Shah

  DOI：10.1039/c6ob01879c

  日期：——

  Radical–radical cross coupling reactions of photoexcited 9-fluorenones have been accomplished for the first time, leading to the synthesis of 9-alkyl, pyrollidinyl and spiro-THF derivatives of 9-fluorenones. The method also reveals, for the first time, the behaviour of ketyl radicals in decarboxyaltive alkylation and ring expansion reactions.

  光激发的9-芴酮的自由基-自由基交叉偶联反应是第一次完成，导致了9-芴酮的9-烷基，吡咯烷基和螺-THF衍生物的合成。该方法还首次揭示了酮基在脱羧烷基化和扩环反应中的行为。
• Schlenk; Bergmann, Justus Liebigs Annalen der Chemie, 1928, vol. 463, p. 208
  作者：Schlenk、Bergmann

  DOI：——

  日期：——
• Practical Synthesis of Unsymmetrical Tetraarylethylenes and Their Application for the Preparation of [Triphenylethylene−Spacer−Triphenylethylene] Triads
  作者：Moloy Banerjee、Susanna J. Emond、Sergey V. Lindeman、Rajendra Rathore

  DOI：10.1021/jo701474y

  日期：2007.10.1

  [GRAPHICS]We have demonstrated that reactions of diphenylmethyllithium with a variety of substituted benzophenones produces corresponding tertiary alcohols that are easily dehydrated, without any need for purification, to produce various unsymmetrical and symmetrical tetraarylethylenes in excellent yields. The simplicity of the method allows for the preparation of a variety of ethylenic derivatives in multigram (10-50 g) quantities with great ease. The methodology was successfully employed for the preparation of various triphenylethylene (TPE)-based triads (i.e., TPE-spacer-TPE) containing polyphenylene and fluoranyl-based spacers. The ready availability of various substituted tetraarylethylenes allowed us to shed light on the effect of substituents on the oxidation potentials (E-ox) of various tetraarylethylenes. Moreover, the electronic coupling among the triphenylethylene moieties in various TPE-spacer-TPE triads was briefly probed by electrochemical and optical methods.
• Schlenk; Bergmann, Justus Liebigs Annalen der Chemie, 1928, vol. 464, p. 28
  作者：Schlenk、Bergmann

  DOI：——

  日期：——
• Studies of 9-Fluorenyl Carbocations. Intramolecular Hydride Migration in a Substituted 9-Fluorenyl Carbocation
  作者：Gabriela Mladenova、Lie Chen、Chris F. Rodriquez、K. W. Michael Siu、Linda J. Johnston、Alan C. Hopkinson、Edward Lee-Ruff

  DOI：10.1021/jo0009200

  日期：2001.2.1

  The substituted fluorenyl cation, 9-(diphenylmethyl)fluoren-9-yl cation (4), is formed under stable ion conditions (low temperature/strong acid) from its corresponding alcohol 3. This ion is transformed to a substituted diphenyl methyl cation 8 at ambient temperature via an apparent 1,2-hydrogen shift. Irradiation of 9-(diphenylmethyl)fluoren-9-ol in methanol gives products derived from the corresponding cation along with radical-derived products from C-C and C-O homolysis processes. The laser flash photolysis of this alcohol gave a transient corresponding to cation 4. All of the photoproducts are derived from cation 4 or radical pathways. High level MO calculations point to a high barrier (23.8 kcal mol(-1)) for the 1,2-hydride shift. This barrier is the consequence of the minimum energy conformation of this fluorenyl cation which is less than ideal for the periplanar geometry necessary for this process.