3,3',5,5'-tetraphenyl-2,2'-dihydroxybiphenyl | 19550-97-1

• 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: 3,3',5,5'-tetraphenyl-2,2'-dihydroxybiphenyl
• 英文别名: 3,3',5,5'-tetraphenyl-2,2'-biphenol；2,2'-Dihydroxy-3,3',5,5'-tetraphenyl-biphenyl；2-(2-Hydroxy-3,5-diphenylphenyl)-4,6-diphenylphenol
• CAS: 19550-97-1
• 化学式: C₃₆H₂₆O₂
• 分子量: 490.601
• InChiKey: XDUKQWGOXVTDEV-UHFFFAOYSA-N

物化性质

• 熔点：
  194-197 °C
• 沸点：
  616.3±50.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,3',5,5'-tetraphenyl-2,2'-dihydroxybiphenyl 在 potassium ferricyanide 、 sodium hydroxide 作用下， 以 乙醚 、 水 为溶剂， 反应 0.17h， 以80%的产率得到3,3',5,5'-tetraphenyl-2,2'-biphenoquinone
  参考文献：
  名称：

  Effect of Aryl Substituents on Intramolecular Cyclization of 2,2’-Biphenoquinones

  摘要：

  Effect of aryl substituents on intramolecular cyclizations of 3,3',5,5'-tetraaryl-2,2'-biphenoquinones (Ar = phenyl (1a) and 4-methoxyphenyl (1b)) has been studied. In benzene, 1a gave 2,4,6,8-tetraphenyldibenzofuran-1-ol (10) gradually as a main product, indicating the phenyl substituents preferred to stabilize the intermediate by delocalization of the negative charge rather than that of the positive one. In contrast, the reaction of 1b occurred spontaneously in order to give a complex mixture, which should be due to 4-methoxyphenyl substituent at the 3 position.

  DOI：

  10.3987/com-08-s(d)57
• 作为产物：
  描述：

  2,2'-二羟基联苯 在 四(三苯基膦)钯 盐酸 、 溴 、 sodium hydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 乙醇 为溶剂， 反应 99.0h， 生成 3,3',5,5'-tetraphenyl-2,2'-dihydroxybiphenyl
  参考文献：
  名称：

  双酚基亚磷酰胺配体用于铜的对映选择性共轭二乙基锌加成反应

  摘要：

  基于邻位取代的双酚和手性胺的亚磷酰胺配体在铜催化的将二烷基锌试剂共轭添加到多种Michael受体中时，诱导出高对映选择性（ee高达99％）。特别是，对于无环硝基烯烃，获得了报道最好的ee。

  DOI：

  10.1021/jo049359m

文献信息

• Counteranion-controlled regioselectivity in palladium-catalyzed allylic amination of dienyl allylic carbonates
  作者：Meng-Lan Shen、Pu-Sheng Wang、Liu-Zhu Gong

  DOI：10.1016/j.tet.2021.131996

  日期：2021.3

  A regioselective Pd-catalyzed allylic amination reaction of dienyl allylic carbonates and aromatic amines has been developed by means of phosphoramidte-palladium catalysis. The regioselectivity could be altered by the counterion of the π-allylpalladium intermediate. As a result, either branched Z-dienyl allylic amines or linear conjugated allylic amines were generated in high levels of regioselectivity

  通过磷酰胺-钯催化已经开发了区域选择性的Pd催化的二烯丙基烯丙基碳酸酯和芳族胺的烯丙基胺化反应。区域选择性可以通过π-烯丙基铝中间体的抗衡离子来改变。结果，通过调节反应条件，从相同的底物以高水平的区域选择性产生支链Z-二烯基烯丙基胺或线性共轭烯丙基胺。
• Biphenol-based ligands for Cu-catalyzed asymmetric conjugate addition
  作者：Alexandre Alexakis、Damien Polet、Cyril Benhaim、Stéphane Rosset

  DOI：10.1016/j.tetasy.2004.05.016

  日期：2004.7

  The synthesis and characterization of seven new phosphoramidite ligands are described, as well as their use in copper-catalyzed 1,4-addition of diethylzine to a wide range of substrates. Enantioselectivities of up to >99.5% are obtained. (C) 2004 Elsevier Ltd. All rights reserved.
• Flash photolysis study of the kinetics of the destruction of mono- and disubstituted phenoxyl radicals
  作者：P. P. Levin、I. V. Khudyakov、V. A. Kuz'min

  DOI：10.1007/bf00961741

  日期：1980.2
• Biphenol-Based Phosphoramidite Ligands for the Enantioselective Copper-Catalyzed Conjugate Addition of Diethylzinc
  作者：Alexandre Alexakis、Damien Polet、Stéphane Rosset、Sébastien March

  DOI：10.1021/jo049359m

  日期：2004.8.1

  Phosphoramidite ligands, based on ortho-substituted biphenols and a chiral amine, induce high enantioselectivities (ee's up to 99%) in the copper-catalyzed conjugate addition of dialkylzinc reagents to a variety of Michael acceptors. Particularly, the best reported ee's were obtained for acyclic nitroolefins.

  基于邻位取代的双酚和手性胺的亚磷酰胺配体在铜催化的将二烷基锌试剂共轭添加到多种Michael受体中时，诱导出高对映选择性（ee高达99％）。特别是，对于无环硝基烯烃，获得了报道最好的ee。
• Effect of Aryl Substituents on Intramolecular Cyclization of 2,2’-Biphenoquinones
  作者：Naoto Hayashi、Takeyuki Akita、Akifumi Kanda、Taku Kamoto、Hiroyuki Higuchi

  DOI：10.3987/com-08-s(d)57

  日期：——

  Effect of aryl substituents on intramolecular cyclizations of 3,3',5,5'-tetraaryl-2,2'-biphenoquinones (Ar = phenyl (1a) and 4-methoxyphenyl (1b)) has been studied. In benzene, 1a gave 2,4,6,8-tetraphenyldibenzofuran-1-ol (10) gradually as a main product, indicating the phenyl substituents preferred to stabilize the intermediate by delocalization of the negative charge rather than that of the positive one. In contrast, the reaction of 1b occurred spontaneously in order to give a complex mixture, which should be due to 4-methoxyphenyl substituent at the 3 position.