1,1-diphenyl-2-tropan-3-yl-ethanol | 95131-86-5

• 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: 1,1-diphenyl-2-tropan-3-yl-ethanol
• 英文别名: 2-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-1,1-diphenylethanol；2-[(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]-1,1-diphenylethanol；1,1-diphenyl-2-(3-tropanyl)ethanol；1,1-diphenyl-2-tropane-3endo-yl-ethanol；1,1-Diphenyl-2-tropan-3endo-yl-aethanol
• CAS: 95131-86-5
• 化学式: C₂₂H₂₇NO
• 分子量: 321.462
• InChiKey: LAOBIJDCKIAALB-ZHPFXUNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  23.47
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,1-diphenyl-2-tropan-3-yl-ethanol 在 盐酸 、 溶剂黄146 作用下， 生成 3endo-(2,2-diphenyl-vinyl)-tropane
  参考文献：
  名称：

  3取代的环戊烷衍生物。三，3取代的戊烷甲醇，烯烃和烷烃。

  摘要：

  DOI：

  10.1021/jm01237a012
• 作为产物：
  描述：

  2-(8-methyl-nortropan-3endo-yl)-1-phenyl-ethanone 、 苯基锂 在 乙醚 作用下， 生成 1,1-diphenyl-2-tropan-3-yl-ethanol
  参考文献：
  名称：

  3取代的环戊烷衍生物。三，3取代的戊烷甲醇，烯烃和烷烃。

  摘要：

  DOI：

  10.1021/jm01237a012

文献信息

• Muscarinic acetycholine receptor antagonists
  申请人：Busch-Petersen Jakob

  公开号：US20070105895A1

  公开（公告）日：2007-05-10

  Muscarinic Acetylcholine Receptor Antagonists and methods of using them are provided.

  提供了肌动蛋白乙酰胆碱受体拮抗剂及其使用方法。
• Design, Synthesis, and Structure−Activity Relationship of Tropane Muscarinic Acetylcholine Receptor Antagonists
  作者：Dramane I. Lainé、Zehong Wan、Hongxing Yan、Chongjie Zhu、Haibo Xie、Wei Fu、Jakob Busch-Petersen、Christopher Neipp、Roderick Davis、Katherine L. Widdowson、Frank E. Blaney、James Foley、Alicia M. Bacon、Edward F. Webb、Mark A. Luttmann、Miriam Burman、Henry M. Sarau、Michael Salmon、Michael R. Palovich、Kristen Belmonte

  DOI：10.1021/jm900736e

  日期：2009.8.27

  Novel tropane derivatives were characterized as muscarinic acetylcholine receptor antagonists (mAChRs). Through optimization of the structure-activity relationship around the tropane scaffold, the quaternary ammonium salt 34 was identified as a very Potent M(3) mAChR antagonist. The compound was functionally active and displayed greater than 24 It duration of action in a mouse model of bronchoconstriction.
• Development of Synthetic Routes, via a Tropinone Intermediate, to a Long-Acting Muscarinic Antagonist for the Treatment of Respiratory Disease
  作者：Robert N. Bream、Doug Hayes、David G. Hulcoop、Alexandra J. Whiteman

  DOI：10.1021/op3002933

  日期：2013.4.19

  This contribution describes the development of two synthetic routes to an investigational muscarinic antagonist for the treatment of chronic obstructive pulmonary disease. The first route used a starting material which was in plentiful supply within the GSK network and was used to make material for early clinical trials and safety assessment studies. Further investigations identified a second, potential long-term manufacturing route from commercially available building blocks, using substrate control to install the two stereocentres with excellent selectivity. A key step was a substrate-directed epoxide reduction which also gave rise to a minor byproduct through a skeletal rearrangement of the tropane ring. A deuterium-labeling experiment was carried out, which shed light on the origin of the byproduct, and also guided the improvement of reaction conditions.
• Discovery of (3-endo)-3-(2-cyano-2,2-diphenylethyl)-8,8-dimethyl-8-azoniabicyclo[3.2.1]octane bromide as an efficacious inhaled muscarinic acetylcholine receptor antagonist for the treatment of COPD
  作者：Zehong Wan、Dramane I. Laine、Hongxing Yan、Chongjie Zhu、Katherine L. Widdowson、Peter T. Buckley、Miriam Burman、James J. Foley、Henry M. Sarau、Dulcie B. Schmidt、Edward F. Webb、Kristen E. Belmonte、Michael Palovich

  DOI：10.1016/j.bmcl.2009.07.006

  日期：2009.8

  Design and syntheses of a novel series of muscarinic antagonists are reported. These efforts have culminated in the discovery of (3-endo)-3-(2-cyano-2,2-diphenylethyl)-8,8-dimethyl-8-azoniabicyclo[3.2.1]octane bromide (4a) as a potent and pan-active muscarinic antagonist as well as a functionally active compound in a murine model of bronchoconstriction. The compound has also displayed pharmacokinetic characteristics suitable for inhaled delivery. (C) 2009 Elsevier Ltd. All rights reserved.
• 3-substituted-8-alkylnortropanes and the acid and quaternary ammonium salts thereof
  申请人：SMITH KLINE FRENCH LAB

  公开号：US02800478A1

  公开（公告）日：1957-07-23