trans-3-Hydroxy-4-(2,3-dimethylphenoxy)-piperidin

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: trans-3-Hydroxy-4-(2,3-dimethylphenoxy)-piperidin
• 英文别名: 3R,4R-4-(2,3-dimethylphenoxy)-3-hydroxypiperidine；(3R,4R)-4-(2,3-dimethylphenoxy)piperidin-3-ol
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: ZHFIAFNZGWCLHU-DGCLKSJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-3-Hydroxy-4-(2,3-dimethylphenoxy)-piperidin 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.83h， 生成 trans-4-(2,3-dimethyl-phenoxy)-6-oxa-1-aza-bicyclo[3.2.1]octan-7-one
  参考文献：
  名称：

  Bicyclic carbamates as inhibitors of papain-like cathepsin proteases

  摘要：

  A 6-oxa-1-aza-bicyclo[3.2.1]octan-7-one system inhibits the proteolytic activity of several cysteine proteases belonging to the papain family. In vitro mechanistic studies and in silico calculations suggest that the minimal pi-overlap between the bridgehead nitrogen and the carbonyl leads to a considerable weakening of the urethane system, making it susceptible to nucleophilic attack from the active site thiol group. The resulting covalent adduct is slowly hydrolyzed, releasing the hydroxypiperidine product of the inhibitor. Synthesis and testing of a set of analogs led to variable protease subtype selectivities ranging from micromolar to nanomolar potencies. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.014
• 作为产物：
  描述：

  1,2,3,6-四氢吡啶 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 sodium carbonate 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 61.0h， 生成 trans-3-Hydroxy-4-(2,3-dimethylphenoxy)-piperidin
  参考文献：
  名称：

  Bicyclic carbamates as inhibitors of papain-like cathepsin proteases

  摘要：

  A 6-oxa-1-aza-bicyclo[3.2.1]octan-7-one system inhibits the proteolytic activity of several cysteine proteases belonging to the papain family. In vitro mechanistic studies and in silico calculations suggest that the minimal pi-overlap between the bridgehead nitrogen and the carbonyl leads to a considerable weakening of the urethane system, making it susceptible to nucleophilic attack from the active site thiol group. The resulting covalent adduct is slowly hydrolyzed, releasing the hydroxypiperidine product of the inhibitor. Synthesis and testing of a set of analogs led to variable protease subtype selectivities ranging from micromolar to nanomolar potencies. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.014

文献信息

• Diastereomers of 4-aryloxy-3-hydroxypiperidines
  申请人：Rattan Singh Balvinder

  公开号：US20050203136A1

  公开（公告）日：2005-09-15

  The present invention relates to essentially pure diastereomers of 4-aryloxy-3-hydroxypiperidines, including purified diastereomers of ifoxetine, methods of purifying said diastereomers, pharmaceutical compositions comprising said diastereomers and methods of treatment utilizing said pharmaceutical compositions.

  本发明涉及基本纯的4-芳氧基-3-羟基哌啶的对映体，包括纯化的异氟西汀对映体，纯化该对映体的方法，包括该对映体的制药组合物以及利用该制药组合物的治疗方法。
• WO2008/51763
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] DIASTEREOMERS OF 4-ARYLOXY-3-HYDROXYPIPERIDINES<br/>[FR] DIASTEREOISOMERES DE 4-ARYLOXY-3-HYDROXYPIPERIDINES
  申请人：BRENTWOOD EQUITIES LTD

  公开号：WO2005023767A3

  公开（公告）日：2005-05-12
• DIASTEREOMERS OF 4-ARYLOXY-3-HYDROXYPIPERIDINES
  申请人：BRENTWOOD EQUITIES LTD.

  公开号：EP1667972B1

  公开（公告）日：2013-06-19
• CATHEPSIN PROTEASES INHIBITORS
  申请人：IRM LLC

  公开号：EP2078027A1

  公开（公告）日：2009-07-15