6-Cyclohexyloxyhexan-1-ol | 1383149-49-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-Cyclohexyloxyhexan-1-ol
• CAS: 1383149-49-2
• 化学式: C₁₂H₂₄O₂
• 分子量: 200.321
• InChiKey: HIFKZHJIMPYECQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-Cyclohexyloxyhexan-1-ol 在 silica gel 、 溶剂黄146 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 29.0h， 生成 (2R,3R,4R,5S)-1-(6-(cyclohexyloxy)hexyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of N-Alkylated Deoxynojirimycin (DNJ) Derivatives for the Treatment of Dengue Virus Infection

  摘要：

  We recently described the discovery of oxygenated N-alkyl deoxynojirimycin (DNJ) derivative 7 (CM-10-18) with antiviral activity against dengue virus (DENY) infection both in vitro and in vivo. This imino sugar was promising but had an EC50 against DENY in BHK cells of 6.5 mu M, which limited its use in in vivo. Compound 7 presented structural opportunities for activity relationship analysis, which we exploited and report here. These structure activity relationship studies led to analogues 2h, 2l, 3j, 3l, 3v, and 4b-4c with nanomolar antiviral activity (EC50 = 0.3-0.5 mu M) against DENY infection, while maintaining low cytotoxicity (CC50 > 500 mu M, SI > 1000). In male Sprague-Dawley rats, compound 3l was well tolerated at a dose up to 200 mg/kg and displayed desirable PK profiles, with significantly improved bioavailability (F = 92 +/- 4%).

  DOI：

  10.1021/jm300171v
• 作为产物：
  描述：

  6-(苄氧基)-1-己醇 在 吡啶 、 palladium 10% on activated carbon 、 氢气 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.5h， 生成 6-Cyclohexyloxyhexan-1-ol
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of N-Alkylated Deoxynojirimycin (DNJ) Derivatives for the Treatment of Dengue Virus Infection

  摘要：

  We recently described the discovery of oxygenated N-alkyl deoxynojirimycin (DNJ) derivative 7 (CM-10-18) with antiviral activity against dengue virus (DENY) infection both in vitro and in vivo. This imino sugar was promising but had an EC50 against DENY in BHK cells of 6.5 mu M, which limited its use in in vivo. Compound 7 presented structural opportunities for activity relationship analysis, which we exploited and report here. These structure activity relationship studies led to analogues 2h, 2l, 3j, 3l, 3v, and 4b-4c with nanomolar antiviral activity (EC50 = 0.3-0.5 mu M) against DENY infection, while maintaining low cytotoxicity (CC50 > 500 mu M, SI > 1000). In male Sprague-Dawley rats, compound 3l was well tolerated at a dose up to 200 mg/kg and displayed desirable PK profiles, with significantly improved bioavailability (F = 92 +/- 4%).

  DOI：

  10.1021/jm300171v

文献信息

• PROCESS FOR PREPARING DIOLS BY HYDROGENATING A CARBOXYLIC ACID-COMPRISING MIXTURE BY MEANS OF COBALT-COMPRISING CATALYSTS
  申请人：PINKOS Rolf

  公开号：US20110124926A1

  公开（公告）日：2011-05-26

  The present invention relates to a process for preparing diols by hydrogenating a mixture comprising carboxylic acid, carboxylic anhydrides and/or carboxylic esters/lactones by means of a cobalt-comprising catalyst, wherein alkali metal and/or alkaline earth metal ions are added to the hydrogenation feed, excluding alkali metal and/or alkaline earth metal ions of mineral acids.

  本发明涉及一种通过使用含钴催化剂氢化包含羧酸、羧酸酐和/或羧酸酯/内酯的混合物来制备二醇的方法，其中向氢化原料中添加碱金属和/或碱土金属离子，但不包括矿酸中的碱金属和/或碱土金属离子。
• VERFAHREN ZUR HERSTELLUNG VON DIOLEN DURCH HYDRIERUNG EINES CARBONSÄURE ENTHALTENDEN GEMISCHES MITTELS KOBALT ENTHALTENDEN KATALYSATOREN
  申请人：BASF SE

  公开号：EP2504300A1

  公开（公告）日：2012-10-03
• US8383866B2
  申请人：——

  公开号：US8383866B2

  公开（公告）日：2013-02-26
• [DE] VERFAHREN ZUR HERSTELLUNG VON DIOLEN DURCH HYDRIERUNG EINES CARBONSÄURE ENTHALTENDEN GEMISCHES MITTELS KOBALT ENTHALTENDEN KATALYSATOREN<br/>[EN] METHOD FOR PRODUCING DIOLS BY HYDROGENATION OF A CARBOXYLIC ACID-CONTAINING MIXTURE USING COBALT-CONTAINING CATALYSTS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE DIOLS PAR HYDROGÉNATION D'UN MÉLANGE CONTENANT DE L'ACIDE CARBOXYLIQUE AU MOYEN DE CATALYSEURS AU COBALT
  申请人：BASF SE

  公开号：WO2011064182A1

  公开（公告）日：2011-06-03

  Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von Diolen durch Hydrierung eines Carbonsäure, Carbonsäureanhydride und/oder Carbonsäureester/Lactone enthaltendes Gemisch mit Hilfe eines Kobalt enthaltenden Katalysators, wobei dem Hydrierzulauf Alkali- und/oder Erdalkaliionen hinzugefügt werden und Alkali- und/oder Erdalkaliionen von Mineralsäuren ausgeschlossen sind.