3',5'-Di-tert-butyl-4-chloro-4'-hydroxy-1,1'-biphenyl | 20031-73-6

• 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-chloro-4'-hydroxy-1,1'-biphenyl
• 英文别名: 4-(p-Chlorophenyl)-2,6-di-t-butylphenol；2,6-ditert-butyl-4-(4-chlorophenyl)phenol
• CAS: 20031-73-6
• 化学式: C₂₀H₂₅ClO
• 分子量: 316.871
• InChiKey: MHXCWAPLZALOOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  22
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3',5'-Di-tert-butyl-4-chloro-4'-hydroxy-1,1'-biphenyl 在 potassium tert-butylate 、 氧气 作用下， 以 叔丁醇 为溶剂， 生成 2,5-Di-tert-butyl-3-(4-chloro-phenyl)-cyclopenta-2,4-dienone
  参考文献：
  名称：

  Base-catalyzed oxygenation of tert-butylated phenols. 2. Formation of 3-aryl-2,5-di-tert-butyl-2,4-cyclopentadienones by base-catalyzed oxygenation of 4-aryl-2,6-di-tert-butylphenols: x-ray structure determination of 2,5-di-tert-butyl-3-(4-chlorophenyl)cyclopentadienone

  摘要：

  DOI：

  10.1021/ja00474a027
• 作为产物：
  描述：

  2,6-Di-tert-butyl-4-(4-chloro-phenyl)-4-hydroxy-cyclohexa-2,5-dienone 以6%的产率得到
  参考文献：
  名称：

  Nishinaga Akira, Kojima Shinya, Mashino Takahiro, Maruyama Kazushige, Chem. Lett, (1994) N 5, S 961-964

  摘要：

  DOI：

文献信息

• Novel Reduction of 2,6-Di-<i>t</i>-butyl-<i>p</i>-quinols with Sodium Borohydride
  作者：Akira Nishinaga、Shinya Kojima、Takahiro Mashino、Kazushige Maruyama

  DOI：10.1246/cl.1994.961

  日期：1994.5

  Reduction of 2,6-di-t-butyl-p-quinols with NaBH4 results unexpectedly in the regio- and stereoselective formation of the corresponding dihydro-p-quinols. The novel reduction occurs via a quinoxyborohydride anion intermediate, which regulates the stereochemistry of the 4- and 6-positions in the products. Aromatization of the products is blocked by the t-butyl groups.

  用 NaBH4 还原 2,6-二叔丁基-对羟基苯酚出人意料地导致相应二氢对羟基苯酚的区域选择性和立体选择性形成。新的还原反应是通过喹氧基硼氢化物阴离子中间体进行的，该中间体调节产物中 4 位和 6 位的立体化学。产物的芳构化被叔丁基阻止。
• Regioselective formation of peroxyquinolatocobalt(III) complexes in the oxygenation of 2,6-di-t-butylphenols with cobalt(II) Schiff-base complexes
  作者：Akira Nishinaga、Haruo Tomita、Kanji Nishizawa、Teruo Matsuura、Shunichiro Ooi、Ken Hirotsu

  DOI：10.1039/dt9810001504

  日期：——

  The oxygenation of 2,6-di-t-butylphenols with five-co-ordinate cobalt(II) Schiff-base complexes in aprotic solvents, such as CH2Cl2, thf, and dmf (thf = tetrahydrofuran, dmf = dimethylformamide), has been found to result in regioselective formation of peroxyquinolatocobalt(III) complexes. The regioselectivity depends on the nature of the substituent at the 4-position of the phenol used: 4-alkyl-2,6-di-t-butylphenols

  在质子惰性溶剂（例如CH 2 Cl 2，thf和dmf（thf =四氢呋喃，dmf =二甲基甲酰胺）中，用五坐标的席夫碱钴（II）Schiff碱络合氧化2,6-二叔丁基苯酚，已发现导致过氧喹诺酮钴（III）配合物的区域选择性形成。区域选择性取决于所用苯酚的4位上取代基的性质：4-烷基-2,6-二叔丁基苯酚（1）提供过氧-对-喹啉钴（III）配合物，而过氧-邻由4-芳基-2,6-二叔丁基苯酚（4）形成喹诺酮络合物。氧合作用的起始是超氧杂钴（III）提取氢。）酚类化合物，得到相应的苯氧基自由基（10）。随后用钴（II）物种快速还原（10），生成了苯并三价酚（III）配合物中间体，其中掺入了双氧。氧化的区域选择性归因于苯酚钴（III）配合物中间体的形成。所述过氧的晶体p -quinolatocobalt（III）复合物（2a）中是斜方晶系，空间群P 2 1 2 1 2 1，具有一个= 33.749（11），b
• Electrochemically Induced S_RN1 Reactions: Selective Substitutions at 1,4-Dichlorobenzene
  作者：Catherine Combellas、Hatem Marzouk、Charles Suba、André Thiébault

  DOI：10.1055/s-1993-25942

  日期：——

  3′,5′-Di-tert-butyl-4-chloro-4′-hydroxy-1,1′-biphenyl was obtained selectively by an electro-induced SRN1 reaction, starting from 1,4-dichlorobenzene and 2,6-di-tert-butylphenoxide. The product was then further substituted to give a phosphine and (phosphoniohenyl)phenoxide zwitterions or carboxylated to obtain 3′,5′-di-tert-butyl-4′-hydroxy-1, 1′-biphenyI-4-carboxylic acid.

  通过电诱导的SRN1反应，选择性地获得了3′,5′-二叔丁基-4-氯-4′-羟基-1,1′-联苯，起始物为1,4-二氯苯和2,6-二叔丁基苯氧化物。随后，将产品进一步取代，生成了膦和（膦基苯）苯氧负离子或羧化，从而获得了3′,5′-二叔丁基-4′-羟基-1,1′-联苯-4-羧酸。
• Linked aryl aryloxypropanolamines as a new class of lipid catabolic agents
  作者：Michael T. Cox、Stuart E. Jaggers、Geraint Jones

  DOI：10.1021/jm00200a008

  日期：1978.2

  The synthesis of a series of stilbene, biaryl, tolane, diaryl ether, sulfide, sulfoxide, and sulfone oxypropanolamines as potential antiobesity agents is described. These compounds were evaluated in a mouse lipid catabolism screen, and the more active members of the series, 4, 57, and 58, were further investigated in rats and dogs. 1-(2,6-Ditert-butyl-4-trans-styrylphenoxy)-3-isopropylamino-2-propanol (4) possessed considerable lipid catabolic activity in mice and caused a significant reduction in the body weight of rats after 5 weeks and of dogs after 6 weeks. Only hematological irregularities in a chronic toxicity study precluded further development of this compound as an alternative antiobesity treatment.
• Field control of regioselectivity in CoIII(salpr)(OH) promoted oxygenation of 4-aryl-2,6-di-tert-butylphenols
  作者：Masafumi Yano、Kazushige Maruyama、Takahiro Mashino、Akira Nishinaga

  DOI：10.1016/0040-4039(95)01099-4

  日期：1995.8