2,6-di-tert-butyl-4-(4-cyanophenyl)phenol | 114460-19-4

• 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: 2,6-di-tert-butyl-4-(4-cyanophenyl)phenol
• 英文别名: 4-(3,5-Ditert-butyl-4-hydroxyphenyl)benzonitrile
• CAS: 114460-19-4
• 化学式: C₂₁H₂₅NO
• 分子量: 307.436
• InChiKey: GWACIUVHHZQYFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  414.8±45.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-di-tert-butyl-4-(4-cyanophenyl)phenol 在 三氯化铝 作用下， 以 甲苯 为溶剂， 生成 氰基联苯酚
  参考文献：
  名称：

  不对称联芳基的选择性电化学和光化学合成及其非线性光学性质

  摘要：

  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。

  DOI：

  10.1039/c39880000203
• 作为产物：
  描述：

  对氯苯甲腈 、 2,6-二叔丁基苯酚 在 4,4'-联吡啶 、 potassium tert-butylate 作用下， 以 氨 为溶剂， 以83%的产率得到2,6-di-tert-butyl-4-(4-cyanophenyl)phenol
  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
• 作为试剂：
  描述：

  N-(1-phenylethyl)furan-2-carboxamide 在 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl benzoate 、 2,6-di-tert-butyl-4-(4-cyanophenyl)phenol 、 potassium hydroxide 作用下， 以 丙酮 为溶剂， 反应 15.0h， 以82%的产率得到糠酰胺
  参考文献：
  名称：

  可见光或近可见光引发的选择性脱除苄基、烯丙基和炔丙基类保护基的方法

  摘要：

  本发明提供了一种可见光或近可见光引发的选择性脱除苄基、烯丙基和炔丙基类保护基的方法，即含苄基、烯丙基或炔丙基类保护基的底物，在酚催化剂、碱、氢源和光的作用下，通过自由基裂解反应，得到目标选择性脱保护基的产物；本方法操作简单，采用安全清洁的可见光或近可见光为激发条件，试剂便宜易得，反应产率高，反应的化学和区域选择性高，适用于各种底物中苄基、烯丙基和炔丙基类保护基的选择性脱除。

  公开号：

  CN113501779B

文献信息

• Palladium-Catalyzed Arylation of 2,6-Di-tert-butylphenol with Aryl Bromides to Produce 1,1′-Biphenyl-4-ol Derivatives
  作者：Yoshiki Kawamura、Tetsuya Satoh、Masahiro Miura、Masakatsu Nomura

  DOI：10.1246/cl.1998.931

  日期：1998.9

  hindered phenol, 2,6-di-tert-butylphenol, efficiently reacts with various bromobenzenes in the presence of a palladium catalyst and a base to selectively afford the corresponding 1,1′-biphenyl-4-ol derivatives.

  空间位阻酚，2,6-二叔丁基苯酚，在钯催化剂和碱的存在下与各种溴苯有效反应，选择性地提供相应的 1,1'-联苯-4-醇衍生物。
• SRN1C-arylation of potassium aryloxides by arylazo phenyl or tert- butyl sulfides in DMSO
  作者：Giovanni Petrillo、Marino Novi、Carlo Dell Erba、Cinzia Tavani、Giovanni Berta

  DOI：10.1016/s0040-4020(01)90095-x

  日期：1990.1

  Aryloxide ions (Ar'O-) behave as C-nucleophiles towards diazosulfides (ArN=NSR; R = Ph, But) leading to unsymmetrical hydroxybiaryls (ArAr'OH) via C-C coupling. The reaction is particularly suited for the synthesis of terms which contain electron-withdrawing groups on the Ar moiety. The SRN1 mechanism is proposed on the grounds of experimental evidences.

  芳氧基离子（Ar'O - ）表现为向diazosulfides C-亲核试剂（ARN = NSR; R = PH，卜吨），导致不对称hydroxybiaryls（ArAr'OH）通过CC耦合。该反应特别适合于在Ar部分上包含吸电子基团的项的合成。S RN 1机制是根据实验证据提出的。
• Synthesis of fluorinated biaryl derivatives via SRN1 reactions
  作者：René Beugelmans、Jacqueline Chastanet

  DOI：10.1016/0040-4039(91)80813-l

  日期：1991.7

  Flourinated biaryl derivatives Y-C6-H4-ArOH (Y = F, CF3, OCF3) are obtained by coupling Y-C6-H4-Br(p) with anions derived from ArOH via a photostimulated SRN1 reaction.

  通过光刺激的S RN 1反应，将YC 6 -H 4 -Br（p）与衍生自ArOH的阴离子偶联，可得到氟化的芳基联芳基衍生物YC 6 -H 4 -ArOH（Y = F，CF 3，OCF 3）。
• Phenoxide and naphthoxide ions as nucleophiles for SRN1 reactions: Synthesis of biphenyl and phenylnaphthyl derivatives
  作者：René Beugelmans、Michèle Bois-Choussy

  DOI：10.1016/s0040-4039(00)80279-8

  日期：1988.1

  Biphenyl or phenylnaphthyl derivatives are obtained by photostimulated SRN1 reactions between the anion of phenols or naphthols and variously substituted haloarenes.

  联苯或苯基萘基衍生物是通过苯酚或萘酚的阴离子与各种取代的卤代芳烃之间的光刺激S RN 1反应获得的。
• 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.