3-phenyl-1,5-dioxa-9-aza-spiro[5.5]undecane | 17385-13-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: 3-phenyl-1,5-dioxa-9-aza-spiro[5.5]undecane
• 英文别名: 3-Phenyl-1,5-dioxa-9-azaspiro<5.5>undecan；3-Phenyl-1,5-dioxa-9-azaspiro[5.5]undecane
• CAS: 17385-13-6
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: PPHSMIAALMJJJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carboxylic acid 、 3-phenyl-1,5-dioxa-9-aza-spiro[5.5]undecane 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 [3-Chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]-(9-phenyl-7,11-dioxa-3-azaspiro[5.5]undecan-3-yl)methanone
  参考文献：
  名称：

  Design and synthesis of spirocyclic compounds as HCV replication inhibitors by targeting viral NS4B protein

  摘要：

  Two novel series of spirocyclic piperidine analogs appended to a pyrazolo[1,5-alpha] pyridine core were designed, synthesized and evaluated for their anti-HCV activity. A series of piperidine ketals afforded dispiro 6p which showed excellent in vitro anti-HCV activities (EC50 of 1.5 nM and 1.2 nM against genotype 1a and 1b replicons, respectively). A series of piperidine oxazolidinones afforded 27c which showed EC50's of 10.9 nM and 6.1 nM against 1a and 1b replicons, respectively. Both compounds 6p and 27c bound directly to non-structural NS4B protein in vitro (IC50's = 10.2 and 30.4 nM, respectively) and exhibited reduced potency in replicons containing resistance mutations encoding changes in the NS4B protein. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.080
• 作为产物：
  描述：

  2-苯基-1,3-丙二醇 在 palladium 10% on activated carbon 、 氢气 、 对甲苯磺酸 作用下， 以 甲醇 、 甲苯 为溶剂， 135.0~140.0 ℃ 、101.33 kPa 条件下， 生成 3-phenyl-1,5-dioxa-9-aza-spiro[5.5]undecane
  参考文献：
  名称：

  Design and synthesis of spirocyclic compounds as HCV replication inhibitors by targeting viral NS4B protein

  摘要：

  Two novel series of spirocyclic piperidine analogs appended to a pyrazolo[1,5-alpha] pyridine core were designed, synthesized and evaluated for their anti-HCV activity. A series of piperidine ketals afforded dispiro 6p which showed excellent in vitro anti-HCV activities (EC50 of 1.5 nM and 1.2 nM against genotype 1a and 1b replicons, respectively). A series of piperidine oxazolidinones afforded 27c which showed EC50's of 10.9 nM and 6.1 nM against 1a and 1b replicons, respectively. Both compounds 6p and 27c bound directly to non-structural NS4B protein in vitro (IC50's = 10.2 and 30.4 nM, respectively) and exhibited reduced potency in replicons containing resistance mutations encoding changes in the NS4B protein. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.080