1-<2-(5-trifluoromethylpyridyl)>-4-hydroxy-3,5-di-t-butylbenzene | 139218-72-7

• 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: 1-<2-(5-trifluoromethylpyridyl)>-4-hydroxy-3,5-di-t-butylbenzene
• 英文别名: 5-Trifluoromethyl-2-(3',5'-di-tert-butyl-4'-hydroxyphenyl)pyridine；2,6-Ditert-butyl-4-[5-(trifluoromethyl)pyridin-2-yl]phenol；2,6-ditert-butyl-4-[5-(trifluoromethyl)pyridin-2-yl]phenol
• CAS: 139218-72-7
• 化学式: C₂₀H₂₄F₃NO
• 分子量: 351.412
• InChiKey: ZUYHLDRBQUNXRG-UHFFFAOYSA-N

物化性质

• 沸点：
  373.4±42.0 °C(Predicted)
• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-<2-(5-trifluoromethylpyridyl)>-4-hydroxy-3,5-di-t-butylbenzene 在 三氟甲磺酸 、 甲苯 作用下， 反应 3.0h， 以80%的产率得到4-(5-(trifluoromethyl)pyridin-2-yl)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
• 作为产物：
  描述：

  2,6-二叔丁基苯酚 、 2-氯-5-三氟甲基吡啶 在 potassium tert-butylate 、 1,2-二氰基苯 作用下， 以 氨 为溶剂， 以50%的产率得到1-<2-(5-trifluoromethylpyridyl)>-4-hydroxy-3,5-di-t-butylbenzene
  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

• SRN1 reactions of chlorotrifluoromethyl pyridines with naphtholate, phenolate and malonate anions
  作者：R Beugelmans

  DOI：10.1016/s0040-4020(01)88013-3

  日期：1993.9.3

  group on position 3, 4, 5 or 6 (2-Cl Py CF3) were found to be suitable substrates for photostimulated SRN1 reactions with nucleophiles derived from 2-naphthol (Nap-OH) or from phenol (PhOH). Carbon-carbon coupling between the regiospecifically generated 2-pyridyl radical and the carbanionic site of the nucleophile yields 2-heterobiaryl derivatives (CF3Py-Nap-OH or CF3Py-PhOH). Similarly, coupling of

  -发现在3、4、5或6位带有CF 3基团的2-氯吡啶（2-Cl Py CF 3）是与来自2-萘酚（Nap-OH）的亲核试剂进行光刺激S RN 1反应的合适底物）或苯酚（PhOH）。区域特异性产生的2-吡啶基基团与亲核试剂的碳负离子位点之间的碳-碳偶联产生2-杂二芳基衍生物（CF 3 Py-Nap-OH或CF 3 Py-PhOH）。类似地，将2-氨基-5-CF 3-3-吡啶基基团偶联产生3-杂联芳基衍生物。丙二酸根阴离子与上述自由基发生偶联。
• 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.