4-[1-Acetoxy-6-(2-naphthyl)hexyl]-5-hydroxy-2(5H)-furanone | 120755-18-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-[1-Acetoxy-6-(2-naphthyl)hexyl]-5-hydroxy-2(5H)-furanone
• 英文别名: [1-(2-hydroxy-5-oxo-2H-furan-3-yl)-6-naphthalen-2-ylhexyl] acetate
• CAS: 120755-18-2
• 化学式: C₂₂H₂₄O₅
• 分子量: 368.43
• InChiKey: IRWIEGQYOGKFCS-UHFFFAOYSA-N

物化性质

• 沸点：
  604.1±55.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(trimethylsilyl)-4-furaldehyde 在 rose bengal 氧气 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 4-[1-Acetoxy-6-(2-naphthyl)hexyl]-5-hydroxy-2(5H)-furanone
  参考文献：
  名称：

  Singlet oxygen oxidation of substituted furans to 5-hydroxy-2(5H)-furanone

  摘要：

  The conditions for the regiospecific singlet oxygen oxidation of various 2,4-disubstituted furans 9 to 4-substituted-2 (5H)-furanones 3 are developed. The presence of a C-2 substituent (e.g., trimethylsilyl, tert-butyldimethylsilyl, or tributylstannyl) in 9 is an absolute requirement for the formation of the 4-substituted-5-hydroxy-2(5H)-furanone regioisomer 3. When the C-2 substituent is triethylsilyl (TES) or TBDMS, however, apart from 3, the corresponding 5-trialkylsiloxy derivative 11 is also isolated in a significant amount. These silyl acetals are unexpectedly stable but can be hydrolyzed back to 3 on stirring with dilute acid. The formation of silyl acetals, to our knowledge, has never been reported in the singlet oxygen oxidation of (trialkylsilyl)furan. A plausible mechanism for their formation is proposed. The presence of a catalytic amount of water in the oxidation of 2-(trialkylsilyl)-4-substituted-furans not only eliminates the formation of the silyl acetals but also speeds up the rate of the oxidation process. Moreover, the oxidation can then be carried out at 0-degrees-C instead of at -78-degrees-C. Oxidation of 2-(1-hydroxyalkyl)-4-substituted-furans in the absence of a reducing agent gives little or no sign of 2,5-disubstituted-6-hydroxy-3(2H)-pyranone 23 but instead 26 selectively. Thus, the (1-hydroxy)alkyl group can be utilized as the trialkylsilyl or trialkylstannyl group in dictating the regioselectivity in the singlet oxygen oxidation of substituted furans.

  DOI：

  10.1021/jo00025a012

文献信息

• [EN] PHARMACEUTICAL COMPOSITIONS CONTAINING 3 AND 4-SUBSTITUTED 2(5H)-FURANONES FOR INHIBITING BONE LOSS<br/>[FR] COMPOSITIONS PHARMACEUTIQUES CONTENANT DES 2(5H)-FURANONES A SUBSTITUTION EN POSITIONS 3 et 4 DESTINEES A INHIBER LES PERTES OSSEUSES
  申请人：ALLERGAN, INC.

  公开号：WO1993021915A1

  公开（公告）日：1993-11-11

  (EN) 3 and 4-substituted 2(5H)-furanone compounds influence the balance between bone production and bone resorption in mammals, including humans. The active compounds are administered to mammals, including humans, in an effective dose which ranges between 0.05 to 100 mg per kilogram, body weight, per day, for the purpose of influencing the balance between bone production and bone resorption, and particularly for treating osteoporosis.(FR) L'invention se rapporte à des composés de 2(5H)-furanone à substitution en positions 3 et 4 qui agissent sur l'équilibre de la formation osseuse et de la résorption osseuse chez les mammifères ainsi que chez l'homme. Les composés actifs sont administrés aux mammifères ainsi qu'à l'homme, en une dose efficace comprise entre 0,05 et 100 mg par kilo/poids/jour afin d'agir sur l'équilibre entre la formation osseuse et la résorption osseuse, et notamment pour traiter l'ostéoporose.

  EN：3 和 4-取代的 2(5H)-furanone 化合物影响哺乳动物（包括人类）骨生成和骨吸取的平衡。活性化合物被给予包括人类在内的哺乳动物，以有效剂量（0.05 到 100 毫克每公斤体重，每日一次），用于影响骨生成和骨吸取的平衡，特别用于治疗骨质疏松。 FR： invention pertient à des com posés de 2(5H)-furanone à substitution en position 3 et 4 qui agissent sur l'équilibre de la formation ossaire et de la dissolution ossaire chez les mammifères et l'iTl homme. Les com posés actifs sont soumis aux mammifères et l'iTl Wesley, en dose effective comprise entre O,05 et 100 mg par kilogramme par jour, avant d'avoir pour objectif d'agir sur l'équilibre entre la formation ossaire et la dissolution ossaire, et en particulier pour traiter l'ostéoporose.
• Anti-inflammatory furanones
  申请人：ALLERGAN, INC

  公开号：EP0295056B1

  公开（公告）日：1992-08-05
• PHARMACEUTICAL COMPOSITIONS CONTAINING 3 AND 4-SUBSTITUTED 2(5H)-FURANONES FOR INHIBITING BONE LOSS
  申请人：ALLERGAN, INC.

  公开号：EP0637240A1

  公开（公告）日：1995-02-08
• US5134128A
  申请人：——

  公开号：US5134128A

  公开（公告）日：1992-07-28
• US5268387A
  申请人：——

  公开号：US5268387A

  公开（公告）日：1993-12-07