(R)-3-(3-methoxyquinuclidin-3-yl)-1,1-diphenylprop-2-yn-1-ol | 515154-67-3

• 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: (R)-3-(3-methoxyquinuclidin-3-yl)-1,1-diphenylprop-2-yn-1-ol
• 英文别名: 3-[(3R)-3-methoxy-1-azabicyclo[2.2.2]octan-3-yl]-1,1-diphenylprop-2-yn-1-ol
• CAS: 515154-67-3
• 化学式: C₂₃H₂₅NO₂
• 分子量: 347.457
• InChiKey: WUMIJQZPHGJALC-JOCHJYFZSA-N

物化性质

• 沸点：
  520.8±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-3-(3-methoxyquinuclidin-3-yl)-1,1-diphenylprop-2-yn-1-ol 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Alkyne–quinuclidine derivatives as potent and selective muscarinic antagonists for the treatment of COPD

  摘要：

  SAR around alkyne-quinuclidine derivatives allowed the discovery of highly potent muscarinic antagonists displaying interesting preferential slow off-rates from the M3 receptor. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.024
• 作为产物：
  描述：

  (3R)-3-ethynyl-1-azabicyclo[2.2.2]oct-3-yl methyl ether 、 二苯甲酮 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.17h， 以83%的产率得到(R)-3-(3-methoxyquinuclidin-3-yl)-1,1-diphenylprop-2-yn-1-ol
  参考文献：
  名称：

  Potent anti-muscarinic activity in a novel series of quinuclidine derivatives

  摘要：

  The synthesis and biological evaluation of a novel family of M-3 muscarinic antagonists are described. A systematic modification of the substituents to a novel alkyne-quinuclidine scaffold yielded original compounds displaying potent in vitro anticholinergic properties. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.079

文献信息

• Quinuclidine derivatives processes for preparing them and their uses as m2 and/or m3 muscarinic receptor inhibitors
  申请人：Guyaux Michel

  公开号：US20050020660A1

  公开（公告）日：2005-01-27

  The invention concerns quinuclidine derivatives of formula I or II wherein the substituents are as defined in the specification, as well as their use as pharmaceuticals. The compounds of the invention_show high affinities for m3 and/or m2 muscarinic receptors and are particularly suited for treating urinary incontinence.

  本发明涉及式I或II的季铵盐衍生物，其中取代基如规范中所定义，以及它们作为药物的用途。本发明的化合物具有高亲和力m3和/或m2胆碱能受体，特别适用于治疗尿失禁。
• Potent anti-muscarinic activity in a novel series of quinuclidine derivatives
  作者：Jean-Philippe Starck、Patrice Talaga、Luc Quéré、Philippe Collart、Bernard Christophe、Patrick Lo Brutto、Sophie Jadot、Dinesh Chimmanamada、Matteo Zanda、Alain Wagner、Charles Mioskowski、Roy Massingham、Michel Guyaux

  DOI：10.1016/j.bmcl.2005.09.079

  日期：2006.1

  The synthesis and biological evaluation of a novel family of M-3 muscarinic antagonists are described. A systematic modification of the substituents to a novel alkyne-quinuclidine scaffold yielded original compounds displaying potent in vitro anticholinergic properties. (c) 2005 Elsevier Ltd. All rights reserved.
• US7361668B2
  申请人：——

  公开号：US7361668B2

  公开（公告）日：2008-04-22
• Alkyne–quinuclidine derivatives as potent and selective muscarinic antagonists for the treatment of COPD
  作者：Jean-Philippe Starck、Laurent Provins、Bernard Christophe、Michel Gillard、Sophie Jadot、Patrick Lo Brutto、Luc Quéré、Patrice Talaga、Michel Guyaux

  DOI：10.1016/j.bmcl.2008.03.024

  日期：2008.4

  SAR around alkyne-quinuclidine derivatives allowed the discovery of highly potent muscarinic antagonists displaying interesting preferential slow off-rates from the M3 receptor. (C) 2008 Elsevier Ltd. All rights reserved.