5-(3-hydroxy-azetidin-1-yl)-5-oxo-2,2-diphenylpentanenitrile | 1355533-23-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(3-hydroxy-azetidin-1-yl)-5-oxo-2,2-diphenylpentanenitrile
• 英文别名: 5-(3-Hydroxyazetidin-1-yl)-5-oxo-2,2-diphenylpentanenitrile
• CAS: 1355533-23-1
• 化学式: C₂₀H₂₀N₂O₂
• 分子量: 320.391
• InChiKey: IRLIMDDKVVBNPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(3-hydroxy-azetidin-1-yl)-5-oxo-2,2-diphenylpentanenitrile 、 甲基氯化镁 在 氯化锆(IV) 作用下， 以 四氢呋喃 为溶剂， 以66%的产率得到5-(3-hydroxyazetidin-1-yl)-5-methyl-2,2-diphenylhexanenitrile
  参考文献：
  名称：

  Development of a Scaleable Synthesis of a Geminal Dimethyl Tertiary Amine as an Inhaled Muscarinic Antagonist for the Treatment of COPD

  摘要：

  An efficient and scalable process for the synthesis of muscarinic antagonist, PF-3635659 1, is described, illustrating redesign of an analogue-targeted synthesis which contained a scale-limiting rhodium-activated C H amination step. The final route includes a reproducible modified Bouveault reaction which has not previously been reported on a substrate of this complexity, or on such a scale with over 5 kg of the requisite gem-dimethylamine prepared via this methodology.

  DOI：

  10.1021/op200233r
• 作为产物：
  描述：

  tert-butyl 4-cyano-4,4-diphenylbutanoate 在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 5-(3-hydroxy-azetidin-1-yl)-5-oxo-2,2-diphenylpentanenitrile
  参考文献：
  名称：

  Development of a Scaleable Synthesis of a Geminal Dimethyl Tertiary Amine as an Inhaled Muscarinic Antagonist for the Treatment of COPD

  摘要：

  An efficient and scalable process for the synthesis of muscarinic antagonist, PF-3635659 1, is described, illustrating redesign of an analogue-targeted synthesis which contained a scale-limiting rhodium-activated C H amination step. The final route includes a reproducible modified Bouveault reaction which has not previously been reported on a substrate of this complexity, or on such a scale with over 5 kg of the requisite gem-dimethylamine prepared via this methodology.

  DOI：

  10.1021/op200233r

文献信息

• Carboxamide derivatives as muscarinic receptor antagonists
  申请人：Glossop Alan Paul

  公开号：US20070105831A1

  公开（公告）日：2007-05-10

  The invention relates to compounds of formula processes and intermediates for their preparation, their use as muscarinic antagonists and pharmaceutical composition containing them.

  本发明涉及具有下列公式的化合物、其制备方法和中间体，以及包含它们的抗胆碱能药物组合物。
• Carboxamide Derivatives As Muscarinic Receptor Antagonists
  申请人：Glossop Paul Alan

  公开号：US20100029720A1

  公开（公告）日：2010-02-04

  The invention relates to compounds of formula processes and intermediates for their preparation, their use as muscarinic antagonists and pharmaceutical composition containing them.

  本发明涉及具有以下式的化合物，以及制备它们的过程和中间体，它们作为毒蕈碱受体拮抗剂的用途和包含它们的制药组合物。
• Azetidine Derivatives as Muscarinic Receptor Antagonists
  申请人：Glossop Paul Alan

  公开号：US20100160279A1

  公开（公告）日：2010-06-24

  The invention relates to compounds of formula (I) processes and intermediates for their preparation, their use as muscarinic antagonists and pharmaceutical compositions containing them.

  本发明涉及公式（I）化合物、其制备过程和中间体，以及它们作为肌肉乙酰胆碱受体拮抗剂的用途和含有它们的药物组合物。
• US7772223B2
  申请人：——

  公开号：US7772223B2

  公开（公告）日：2010-08-10
• US8268881B2
  申请人：——

  公开号：US8268881B2

  公开（公告）日：2012-09-18