2-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-methoxybenzoxazole | 29078-05-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-methoxybenzoxazole
• 英文别名: 2-(3,5-di-t-butyl-4-hydroxyphenyl)-5-methoxybenzoxazole；2,6-di-tert-butyl-4-(5-methoxybenzo[d]oxazol-2-yl)phenol；2,6-di-tert-butyl-4-(5-methoxy-benzooxazol-2-yl)-phenol；2-(3,5-Di-tert-butyl-4-hydroxyphenyl)-5-methoxybenzoxazole；2,6-ditert-butyl-4-(5-methoxy-1,3-benzoxazol-2-yl)phenol
• CAS: 29078-05-5
• 化学式: C₂₂H₂₇NO₃
• 分子量: 353.461
• InChiKey: UWNCPUDYIXKLDS-UHFFFAOYSA-N

物化性质

• 熔点：
  177-178 °C(Solv: methanol (67-56-1))
• 沸点：
  433.0±45.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  55.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-methoxybenzoxazole 、 碳酸氢钠 在 三溴化硼 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-hydroxybenzoxazole
  参考文献：
  名称：

  Compounds useful as neuro-protective agents

  摘要：

  本发明涉及新颖的苯基噁唑、噻唑、噁唑啉、噁二唑和苯并噁唑，它们作为神经保护剂具有效用。

  公开号：

  US06156748A1
• 作为产物：
  描述：

  4-甲氧基-2-硝基酚 、 2,6-二叔丁基-4-甲基苯酚 在 铁粉 、 sulfur 作用下， 以 邻二氯苯 为溶剂， 反应 24.0h， 以76%的产率得到2-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-methoxybenzoxazole
  参考文献：
  名称：

  Redox-Neutral Iron–Sulfur Promoted Transformation of 2-Nitrophenols and 2,6-Disubstituted p-Cresols into 2-Arylbenzoxazoles

  摘要：

  A catalyst based on iron and elemental sulfur has been shown to efficiently promote a redox-neutral reaction between 2-nitrophenols and 2,6-disubstituted p-cresols, allowing for the preparation of 2-arylbenzoxazoles in good yields. This synthetic methodology also affords high atom economy without the use of any external oxidizing and/or reducing reagents. This is the first redox-condensation reaction of 2-nitrophenols with 2,6-disubstituted p-cresols.

  DOI：

  10.1055/s-0033-1338995

文献信息

• Studies on the synthesis and anti-inflammatory activity of 2,6-di-tert-butylphenols with a heterocyclic group at the 4-position. I.
  作者：YASUO ISOMURA、NORIKI ITO、HIROSHIGE HOMMA、TETSUSHI ABE、KAZUO KUBO

  DOI：10.1248/cpb.31.3168

  日期：——

  A number of 2, 6-di-tert-butylphenols with a heterocyclic group at the 4-position were prepared. The heterocyclic groups were as follows : benzoxazole, benzothiazole, benzimidazole, indole, imidazo [1, 2-a] pyridine and imidazo [1, 2-a] pyrimidine. Anti-inflammatory activity of these compounds was examined by using the adjuvant-induced arthritis (A. A) assay. Some compounds were further tested in carrageenin-induced rat paw edema (CIPE) assay and AcOH-induced writhing (AIW) assay in mice. The anti-inflammatory activity was greatly dependent on the value of the heterocyclic group. Among these compounds, 2-(3, 5-di-tert-butyl-4-hydroxyphenyl)-benzoxazole (IIa) and 2-(3, 5-di-tert-butyl-4-hydroxyphenyl) indole (Xg) showed very potent activity. Both IIa and Xg had a minimum effective dose of 5 mg/kg (p. o.) in A. A assay and showed stronger activity than phenylbutazone in CIPE assay but weaker analgesic activity than aminopyrine in AIW assay.

  制备了一系列在4位含有杂环基团的2,6-二叔丁基苯酚。这些杂环基团包括：苯并噁唑、苯并噻唑、苯并咪唑、吲哚、咪唑[1,2-a]喹啉和咪唑[1,2-a]嘧啶。这些化合物的抗炎活性通过佐剂诱导的关节炎（A.A）测定进行评估。部分化合物在卡拉胶诱导的大鼠足肿胀（CIPE）测定和醋酸诱导的小鼠扭动（AIW）测定中进一步测试。这些化合物的抗炎活性在很大程度上取决于杂环基团的性质。在这些化合物中，2-(3,5-二叔丁基-4-羟基苯基)苯并噁唑（IIa）和2-(3,5-二叔丁基-4-羟基苯基)吲哚（Xg）表现出非常强的活性。IIa和Xg在A.A测定中的最小有效剂量为5 mg/kg（口服），在CIPE测定中显示出比苯基布托松更强的活性，但在AIW测定中的镇痛活性则弱于氨基吡啶。
• NOVEL COMPOUNDS USEFUL AS NEURO-PROTECTIVE AGENTS
  申请人：——

  公开号：US20010027194A1

  公开（公告）日：2001-10-04

  This invention relates to novel phenyl oxazoles, thiazoles, oxazolines, oxadiazoles and benzoxazoles useful as neuro-protective agents.

  这项发明涉及新颖的苯基噁唑、噻唑、噁唑啉、噁二唑和苯并噁唑，可用作神经保护剂。
• [EN] NOVEL COMPOUNDS USEFUL AS NEURO-PROTECTIVE AGENTS<br/>[FR] NOUVEAUX COMPOSES UTILES COMME AGENTS NEURO-PROTECTEURS
  申请人：ELI LILLY AND COMPANY

  公开号：WO1998015274A1

  公开（公告）日：1998-04-16

  (EN) This invention relates to novel phenyl oxazoles, thiazoles, oxazolines, oxadiazoles and benzoxazoles useful as neuro-protective agents.(FR) L'invention concerne de nouveaux phényle oxazoles, thiazoles, oxazolines, oxadiazoles et benzoxazoles pouvant être utilisés comme agents neuro-protecteurs.

  这项发明涉及一种新型的苯基噁唑、噻唑、噁唑啉、噁二唑和苯并噁唑，可用作神经保护剂。
• Novel compounds useful as neuro-protective agents
  申请人：——

  公开号：US20020177595A1

  公开（公告）日：2002-11-28

  This invention relates to novel phenyl oxazoles, thiazoles, oxazolines, oxadiazoles and benzoxazoles useful as neuro-protective agents.

  本发明涉及新的苯基噁唑，噻唑，噁唑啉，噁二唑和苯并噁唑，可用作神经保护剂。
• Methods of using novel compounds as neuro-protective agents
  申请人：——

  公开号：US20030050311A1

  公开（公告）日：2003-03-13

  This invention relates to novel phenyl oxazoles, thiazoles, oxazolines, oxadiazoles and benzoxazoles useful as neuro-protective agents.

  本发明涉及新型苯基噁唑、噻唑、噁唑啉、噁二唑和苯并噁唑，其作为神经保护剂具有用途。