5-cyano-2-(3',5'-di-tert-butyl-4'-hydroxyphenyl)pyridine | 114460-18-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-cyano-2-(3',5'-di-tert-butyl-4'-hydroxyphenyl)pyridine
• 英文别名: 6-(3,5-Ditert-butyl-4-hydroxyphenyl)pyridine-3-carbonitrile
• CAS: 114460-18-3
• 化学式: C₂₀H₂₄N₂O
• 分子量: 308.423
• InChiKey: HALXGPUMYUOZBS-UHFFFAOYSA-N

物化性质

• 沸点：
  415.2±45.0 °C(predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  56.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-氯-3-氰基吡啶 、 2,6-二叔丁基苯酚 在 potassium tert-butylate 、 1,2-二氰基苯 作用下， 以 氨 为溶剂， 以77%的产率得到5-cyano-2-(3',5'-di-tert-butyl-4'-hydroxyphenyl)pyridine
  参考文献：
  名称：

  Electrosynthesis of Unsymmetrical Polyaryls by a SRN1-Type Reaction

  摘要：

  Unsymmetrical polyaryls are electrosynthesized in liquid ammonia by a single-step S(RN)1 reaction in the presence of a redox mediator starting from aromatic halides and 2,6-di-tert-butyl phenoxide. With monoaryl halides activated by electron-withdrawing substituents (N of pyridyl or quinolyl, trifluoromethyl, cyano, sulfone, ester, ketone, alkyl sulfide, N+ of anilinium), biaryls are obtained in good yields (between 50 and 95%). The yields of ter- and quateraryls are lower (40% maximum). The reaction is extended to other ortho-disubstituted phenols. Elimination reactions of the tert-butyl groups from the products are achieved by a Friedel-Crafts reaction using either trifluoromethanesulfonic acid or aluminum trichloride as catalysts.

  DOI：

  10.1021/jo00095a024

文献信息

• Selective electrochemical and photochemical syntheses of unsymmetrical biaryls and their non-linear optical properties
  作者：Catherine Combellas、H�l�ne Gautier、Jacques Simon、Andr� Thiebault、Fran�ois Tournilhac、Marguerite Barzoukas、Dominique Josse、Isabelle Ledoux、Christian Amatore、Jean-No�l Verpeaux

  DOI：10.1039/c39880000203

  日期：——

  A selective synthesis of unsymmetrically substituted electron donor/electron acceptor biaryls is described which is based on an electrochemically or photochemically induced SRN1 reaction; the optical hyperpolarizability coefficients β are determined in solution for the various reaction products and found to be of the same order of magnitude as that of 4-nitro-aniline.

  描述了基于电化学或光化学诱导的S RN 1反应的不对称取代的电子给体/电子受体联芳基的选择性合成；在溶液中确定各种反应产物的光学超极化率系数β，发现其与4-硝基苯胺具有相同的数量级。
• Theory and experimental illustration of preparative electrochemistry using redox catalysis of electron transfer initiated radical chain reactions. Application to the cross-coupling between aryl halides and phenoxide ions
  作者：N. Alam、Christian Amatore、C. Combellas、A. Thiebault、J. N. Verpeaux

  DOI：10.1021/jo00313a022

  日期：1990.12

  A general equation predicting the yield of electron transfer initiated radical chain reaction (S(RN)1 and related mechanisms) under preparative electrochemical conditions is given for situations where the electron-transfer activation of the chain is performed by means of a redox mediator. Simple tests, allowing for the choice of proper redox mediator, are given, and their origins established and discussed. The validity and application of this simple model is shown and discussed for the case of the S(RN)1-like reaction involving di-tert-butylphenoxide as a nucleophile, to afford biaryls of interest for their properties in nonlinear optics.