2-(5,5,6-trimethylbicyclo[2.2.1]hept-exo-2-yl)phenol | 4680-20-0

• 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: 2-(5,5,6-trimethylbicyclo[2.2.1]hept-exo-2-yl)phenol
• 英文别名: (+/-)-2-(5,5,6exo-Trimethyl-[2exo]norbornyl)-phenol；(+/-)-2-(5,5,6exo-Trimethyl-norbornyl-(2exo))-phenol；6-exo-o-Hydroxyphenyl-exo-isocamphan；2-[(1R,2S,4R,6S)-5,5,6-trimethyl-2-bicyclo[2.2.1]heptanyl]phenol
• CAS: 4680-20-0；24190-36-1
• 化学式: C₁₆H₂₂O
• 分子量: 230.35
• InChiKey: RJZHQMOKFMOSQY-OIMNJJJWSA-N

物化性质

• 沸点：
  285.5±9.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  2-(5,5,6-trimethylbicyclo[2.2.1]hept-exo-2-yl)phenol 生成 6-exo-Acetyl-exo-isocamphan
  参考文献：
  名称：

  The Condensation of Camphene and Phenol. Product Formation via a Direct 2,6-Hydride Transfer

  摘要：

  DOI：

  10.1021/ja01068a025
• 作为产物：
  描述：

  isobornyl-phenyl ether 在 三氟化硼乙醚 、 苯 作用下， 生成 2-(5,5,6-trimethylbicyclo[2.2.1]hept-exo-2-yl)phenol
  参考文献：
  名称：

  萜烯酚和酚醚。

  摘要：

  DOI：

  10.1021/ja01191a019

文献信息

• Tandem molecular rearrangement in the alkylation of phenol with camphene
  作者：I. Yu. Chukicheva、L. V. Spirikhin、A. V. Kuchin

  DOI：10.1134/s1070428008010077

  日期：2008.1

  The alkylation of phenol with camphene in the presence of boron trifluoride in glacial acetic acid was accompanied by tandem molecular rearrangement with formation of a mixture of ortho- and para-substituted phenols having 1,7,7-trimethylbicyclo[2.2.1]hept-exo-2-yl and 5,5,6-trimethylbicyclo[2.2.1]hept-exo-2-yl substituents. The same products were obtained by rearrangement of 1,7,7-trimethylbicyclo[2.2.1]hept-exo-2-yloxybenzene under analogous conditions. Similar reactions performed in the presence of aluminum phenoxide as catalyst resulted in predominant formation of the corresponding ortho-substituted phenols.

  在冰醋酸中，在三氟化硼存在下，苯酚与莰发生烷基化反应，同时发生串联分子重排反应，形成具有 1,7,7- 三甲基双环[2.2.1]庚-外-2-基和 5,5,6- 三甲基双环[2.2.1]庚-外-2-基取代基的正对和对位取代苯酚混合物。在类似条件下，1,7,7-三甲基双环[2.2.1]庚-外-2-基苯通过重排也得到了相同的产物。在有苯氧化铝作为催化剂的情况下进行的类似反应主要生成了相应的正交取代酚。
• Aluminum phenoxide-promoted alkylation of phenol with α- and β-pinenes
  作者：A. V. Kutchin、O. A. Shumova、I. Yu. Chukicheva

  DOI：10.1007/s11172-013-0062-9

  日期：2013.2

  Alkylation of phenol with natural α- and β-pinenes in the presence of Al(OPh)3 gives the O- and C-alkylation products with the structurally different terpene fragments. The terpenophenols obtained have proved to be optically active.

  在 Al(OPh)3 存在下，苯酚与天然 α-和 β-蒎烯进行烷基化，得到具有结构不同萜烯片段的 O-和 C-烷基化产物。所获得的萜酚已被证明具有光学活性。
• Evaluation of antiviral activity of terpenophenols and some of their N- and O-derivatives
  作者：I. Yu. Chukicheva、E. V. Buravlev、I. A. Dvornikova、I. V. Fedorova、V. V. Zarubaev、A. V. Slita、Ya. L. Esaulkova、A. V. Kutchin

  DOI：10.1007/s11172-022-3676-y

  日期：2022.11

  comparative evaluation of the antiviral activity of a number of new and previously synthesized terpenophenols and their N- or O-containing derivatives against the A/Puerto Rico/8/34 (H1N1) virus strain was carried out. 2-Isobornylphenol, 1,2-dihydroxy-6-isobornyl-4-methylbenzene, 2-isobornyl-1,4-benzoquinone, and N-butyl-4-hydroxy-3,5-diisobornylbenzamide showed the highest activity.

  对一些新的和先前合成的萜酚及其含氮或含氧衍生物针对 A/Puerto Rico/8/34 (H1N1) 病毒株的抗病毒活性进行了比较评估。 2-异冰片基苯酚、1,2-二羟基-6-异冰片基-4-甲基苯、2-异冰片基-1,4-苯醌和N-丁基-4-羟基-3,5-二异冰片基苯甲酰胺显示出最高的活性。
• Certain features of the alkylation of phenol by borneol and isoborneol catalyzed by aluminum alkoxides
  作者：I. Yu. Chukicheva、I. V. Fedorova、V. A. Yagolˈnitskaya、A. V. Kuchin

  DOI：10.1007/s10600-011-9828-1

  日期：2011.3

  Phenol was alkylated by borneol and its stereoisomer isoborneol in the presence of aluminum phenolate and isopropylate. The reaction products were isolated and characterized. Certain features of the process were defined.

  在苯酚铝和异丙醇铝存在下，苯酚被冰片及其立体异构体异冰片烷基化。分离并表征反应产物。定义了该过程的某些特征。
• Alkylation of aluminum phenolate with unsaturated monoterpenes
  作者：A. V. Kutchin、I. Yu. Chukicheva、I. V. Fedorova、O. A. Shumova

  DOI：10.1134/s0012500811040124

  日期：2011.4