3''',5'''-Di-tert-butyl-4'''-hydroxy-<1,1':4',1'':4'',1'''-quaterphenyl>-4-carbonitrile | 139780-24-8

• 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''',5'''-Di-tert-butyl-4'''-hydroxy-<1,1':4',1'':4'',1'''-quaterphenyl>-4-carbonitrile
• 英文别名: 4-[4-[4-(3,5-Ditert-butyl-4-hydroxyphenyl)phenyl]phenyl]benzonitrile；4-[4-[4-(3,5-ditert-butyl-4-hydroxyphenyl)phenyl]phenyl]benzonitrile
• CAS: 139780-24-8
• 化学式: C₃₃H₃₃NO
• 分子量: 459.631
• InChiKey: KXZDCYPOJSRQJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4,4'-二溴联苯 在 钯 4,4'-联吡啶 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 氨 为溶剂， 生成 3''',5'''-Di-tert-butyl-4'''-hydroxy-<1,1':4',1'':4'',1'''-quaterphenyl>-4-carbonitrile
  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

• Electrosynthesis of unsymmetrical donor-acceptor polyaryls
  作者：P. Boy、C. Combellas、A. Thiébault、C. Amatore、A. Jutand

  DOI：10.1016/s0040-4039(00)93977-7

  日期：1992.1

  Unsymmetrical Donor-Acceptor Polyaryls are synthesized by an electrochemically induced SRN1 reaction using 2,6-ditertbutyl phenoxide as nucleophile and acceptor substituted polyarylbromides The latter are synthesized by a cross coupling reaction of aromatic organometallic reagents and aromatic halides catalyzed by palladium complexes.

  不对称的供体-受体聚芳基是通过电化学诱导的S RN 1反应合成的，使用2,6-二叔丁基苯氧化物作为亲核试剂和受体取代的聚芳基溴化物。后者是通过钯配合物催化的芳族有机金属试剂与芳族卤化物的交叉偶联反应合成的。
• Electrosynthesis of Unsymmetrical Polyaryls by a SRN1-Type Reaction
  作者：P. Boy、C. Combellas、C. Suba、A. Thiebault

  DOI：10.1021/jo00095a024

  日期：1994.8

  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.