1-(3',5'-Di-tert-butyl-4'-hydroxybiphenyl-4-yl)ethanone | 20031-75-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3',5'-Di-tert-butyl-4'-hydroxybiphenyl-4-yl)ethanone
• 英文别名: 4-acetyl-3',5'-di-tert-butyl-4'-hydroxybiphenyl；2,6-di-tert-butyl-4-(4-acetylphenyl)phenol；1-(3',5'-ditert-butyl-4'-hydroxy-1,1'-biphenyl-4-yl)ethanone；3,5-Di-tert.-butyl-4'-acetyl-biphenyl-4-ol；4-(4-Acetophenyl)-2,6-di-tert-butylphenol；1-[4-(3,5-ditert-butyl-4-hydroxyphenyl)phenyl]ethanone
• CAS: 20031-75-8
• 化学式: C₂₂H₂₈O₂
• 分子量: 324.463
• InChiKey: OJYVKOJVYHOLBN-UHFFFAOYSA-N

物化性质

• 沸点：
  416.3±45.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3',5'-Di-tert-butyl-4'-hydroxybiphenyl-4-yl)ethanone 在 三氟甲磺酸 、 甲苯 作用下， 反应 2.0h， 以65%的产率得到1-[4-(4-羟基苯基)苯基]乙酮
  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 、 对氯苯乙酮 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-(3',5'-Di-tert-butyl-4'-hydroxybiphenyl-4-yl)ethanone
  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-(naphthalen-2-ylmethyl)-3-phenylpropanamide 在 cesium hydroxide 、 4-methoxy-2,2,6,6-tetramethylpiperidin-1-ol 、 1-(3',5'-Di-tert-butyl-4'-hydroxybiphenyl-4-yl)ethanone 作用下， 以 乙腈 为溶剂， 反应 40.0h， 以81%的产率得到3-苯基丙酰胺
  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

• Developing potential agents against atherosclerosis: Design, synthesis and pharmacological evaluation of novel dual inhibitors of oxidative stress and Squalene Synthase activity
  作者：Maria G. Katselou、Alexios N. Matralis、Angeliki P. Kourounakis

  DOI：10.1016/j.ejmech.2017.06.042

  日期：2017.9

  present the design, synthesis and pharmacological evaluation of novel dual-acting molecules as a therapeutic approach for atherosclerosis. Analogues 1–10 were rationally designed through structural modifications of their parent compounds (A-E) in order for structure-activity relationship studies to be carried out. Most compounds showed a significant inhibition against Squalene Synthase activity exhibiting

  对于多因素和复杂疾病的治疗，与仅对单个靶标具有高特异性的化合物相比，作用于多个靶标的化合物通常具有更高的疗效，这一点已变得越来越明显。在先前研究证明吗啉和1,4-苯并（x / thi）嗪衍生物（AE）具有重要的抗氧化和降血脂作用的基础上，我们在此介绍新型双作用分子作为药物的设计，合成和药理学评价。动脉粥样硬化的治疗方法。类似物1–10是通过对其母体化合物（AE），以便进行结构-活性关系研究。大多数化合物显示出对角鲨烯合酶活性的显着抑制作用，同时显示出非常有效的多峰抗氧化剂（抗脂质过氧化和自由基清除剂）作用，从而使2-芳基-1,4-苯并（x / thia）zin-2-ol支架是用于设计有效抗氧化剂的出色药效基团。最后，尽管保留了（抗高胆固醇血症）活性甚至改善了（抗高血脂血症）活性，但用其各自的1,4-苯并噻嗪（化合物4）代替了铅化合物D的八氢-1,4-苯并恶嗪部分。保留D的抗糖尿病作用。
• Derivatives of heterocycles with 5 members, their preparation and their use as medicaments
  申请人：——

  公开号：US20040132788A1

  公开（公告）日：2004-07-08

  The invention relates to thiazole, oxazole, imidazole, isoxazole and isoxazoline derivatives of general formula (I) 1 wherein Het is thiazole, oxazole, imidazole, isoxazole or isoxazoline, n is an integer from 0 to 6, A is notably selected from various optionally substituted aromatic radicals, B is notably hydrogen, alkyl or phenyl, R 1 and R 2 are notably independently hydrogen, alkyl or cycloalkyl and &OHgr; is —NR 46 R 47 or —OR 48 R 46 and R 47 are notably independently hydrogen, alkyl, cycloalkyl or —(CH 2 ) k —COOR 51 , R 51 is notably alkyl or haloalkyl and R 48 is notably hydrogen or alkyl. These compounds have advantageous pharmacological properties which allow their use in therapeutics, notably for treating neurodegenerative disorders or pain.

  本发明涉及噻唑、噁唑、咪唑、异噁唑和异噁唑啉的一般式(I)衍生物，其中Het为噻唑、噁唑、咪唑、异噁唑或异噁唑啉，n为0至6的整数，A特别选自各种可任选取代的芳香族基团，B特别为氢、烷基或苯基，R1和R2特别独立地为氢、烷基或环烷基，Ω为—NR46R47或—OR48，R46和R47特别独立地为氢、烷基、环烷基或—(CH2)k—COOR51，R51特别为烷基或卤代烷基，R48特别为氢或烷基。这些化合物具有有利的药理学特性，使其可用于治疗学，特别是用于治疗神经退行性疾病或疼痛。
• New Multifunctional Di-<i>tert</i>-butylphenoloctahydro(pyrido/benz)oxazine Derivatives with Antioxidant, Antihyperlipidemic, and Antidiabetic Action
  作者：Eleni Ladopoulou、Alexios N. Matralis、Angeliki P. Kourounakis

  DOI：10.1021/jm400101e

  日期：2013.4.25

  Compound 2 also indicated a good anti-inflammatory activity, decreasing edema by 44%, while it was further evaluated for its antidiabetic activity using a type 2 diabetes experimental mouse model. After 7 weeks of administration, it produced a significant antihyperglycemic and antihyperlipidemic activity. In conclusion, rational drug design led to a compound combining improved antioxidant, antidyslipidemic

  氧化应激，炎症和高脂血症是动脉粥样硬化和2型糖尿病的病理生理学中涉及的常见因素。我们以前已经开发了具有抗氧化剂和抗动脉粥样硬化特性的多功能抗血脂异常衍生物。我们现在报告设计，合成和评估两个这样的新型衍生物，其中包含抗糖尿病药琥珀醇的结构部分。新化合物在体外抗氧化剂和角鲨烯合酶的抑制活性（在较低的微摩尔浓度下）表现出极大的改善，并且具有显着的降血脂作用，可将血浆总胆固醇，甘油三酸酯和MDA降低65-90％。化合物2还显示出良好的抗炎活性，可将水肿减少44％，同时使用2型糖尿病实验小鼠模型进一步评估了其抗糖尿病活性。给药7周后，它产生了显着的降血糖和降血脂活性。总之，合理的药物设计导致了一种结合了改进的抗氧化剂，抗血脂异常和抗糖尿病作用的化合物，这些化合物可作为代谢综合征的潜在治疗策略。
• 4-PHENYLTHIAZOLE AND 4-PHENYLIMIDIZOLE DERIVATIVES AND THEIR USE AS MEDICAMENTS FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES, PAIN AND EPILEPSY
  申请人：CHABRIER de LASSAUNIERE Pierre-Etienne

  公开号：US20080108683A1

  公开（公告）日：2008-05-08

  The invention relates to novel derivatives of 4-phenylthiazoles and 4-phenylimidizoles and the use thereof as medicaments. The invention especially relates to the following compounds: butyl-2-[4-(4-aminophenyl)-1H-imidizol-2-yl]ethyl-carbamate, and 4-[2-(1-aminocyclopentyl)-1,3-thiazol-4-yl]-2,6-di-tert-butylphenol, and the salts of the same.

  本发明涉及4-苯基噻唑和4-苯基咪唑的新衍生物及其作为药物的用途。本发明特别涉及以下化合物：丁基-2-[4-(4-氨基苯基)-1H-咪唑-2-基]乙基-氨基甲酸酯，以及4-[2-(1-氨基环戊基)-1,3-噻唑-4-基]-2,6-二叔丁基苯酚及其盐。
• 4-Phenlthiazole and 4-phenylimidizole derivatives and their use as medicaments for the treatment of neurodegenerative diseases, pain and epilepsy
  申请人：Chabrier de Lassauniere Pierre-Etienne

  公开号：US20070054900A1

  公开（公告）日：2007-03-08

  The invention relates to novel derivatives of 4-phenylthiazoles and 4-phenylimidazoles and the use thereof medicament. The invention especially relates to the following compounds: butyl-2-[4-(4-(aminophenyl)-1H-imidazol-2-yl]ethyl-carbamate, and 4-[2-(1-aminocyclopentyl)-1,3-thiazol-4-yl]-2,6-di-tert-butylphenol, and the salts of the same.

  该发明涉及4-苯基噻唑和4-苯基咪唑的新衍生物及其药物用途。该发明特别涉及以下化合物：丁基-2-[4-(4-(氨基苯基)-1H-咪唑-2-基)]乙基氨基甲酸酯，以及4-[2-(1-氨基环戊基)-1,3-噻唑-4-基]-2,6-二叔丁基苯酚，以及其盐。