(2S,3S,5R)-2-azido-1-(3,5-difluoro-phenoxy)-5-methoxy-6-(4,4,4-trifluoro-butoxy)-hexan-3-ol | 1221400-86-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S,3S,5R)-2-azido-1-(3,5-difluoro-phenoxy)-5-methoxy-6-(4,4,4-trifluoro-butoxy)-hexan-3-ol
• 英文别名: 2-azido-1-(3,5-difluoro-phenoxy)-5-methoxy-6-(4,4,4-trifluoro-butoxy)-hexan-3-ol
• CAS: 1221400-86-7
• 化学式: C₁₇H₂₂F₅N₃O₄
• 分子量: 427.371
• InChiKey: DFILSTJHTLNSOV-PMPSAXMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  29.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  96.68
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,5R)-2-azido-1-(3,5-difluoro-phenoxy)-5-methoxy-6-(4,4,4-trifluoro-butoxy)-hexan-3-ol 在 5% Pd(II)/C(eggshell) 、 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  P2′-truncated BACE-1 inhibitors with a novel hydroxethylene-like core

  摘要：

  Highly potent BACE-1 protease inhibitors derived from a novel hydroxyethylene-like core structure were recently developed by our group using X-ray crystal structure data and molecular modelling. In a continuation of this work guided by molecular modelling we have explored a truncated core motif where the P2' amide group is replaced by an ether linkage resulting in a set of alkoxy, aryloxy and alkylaryl groups, with the overall aim to reduce molecular weight and the number of amide bonds to increase permeability and bestow the inhibitors with drug-like features. The most potent of these inhibitors displayed a BACE-I IC50 value of 140 nM. The synthesis of these BACE-I inhibitors utilizes readily available starting materials, furnishing the target compounds in good overall yields. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.10.041
• 作为产物：
  描述：

  (2R,4S,5S)-5-azido-6-(3,5-difluoro-phenoxy)-2-methoxyhexane-1,4-diol 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 、 叔丁胺氢碘酸盐 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.5h， 以36%的产率得到(2S,3S,5R)-2-azido-1-(3,5-difluoro-phenoxy)-5-methoxy-6-(4,4,4-trifluoro-butoxy)-hexan-3-ol
  参考文献：
  名称：

  P2′-truncated BACE-1 inhibitors with a novel hydroxethylene-like core

  摘要：

  Highly potent BACE-1 protease inhibitors derived from a novel hydroxyethylene-like core structure were recently developed by our group using X-ray crystal structure data and molecular modelling. In a continuation of this work guided by molecular modelling we have explored a truncated core motif where the P2' amide group is replaced by an ether linkage resulting in a set of alkoxy, aryloxy and alkylaryl groups, with the overall aim to reduce molecular weight and the number of amide bonds to increase permeability and bestow the inhibitors with drug-like features. The most potent of these inhibitors displayed a BACE-I IC50 value of 140 nM. The synthesis of these BACE-I inhibitors utilizes readily available starting materials, furnishing the target compounds in good overall yields. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.10.041