(3R,4R)-1-benzyl-4-(3,4-difluorophenyl)-4-hydroxypiperidine-3-carbonitrile | 1247091-38-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3R,4R)-1-benzyl-4-(3,4-difluorophenyl)-4-hydroxypiperidine-3-carbonitrile
• CAS: 1247091-38-8
• 化学式: C₁₉H₁₈F₂N₂O
• 分子量: 328.362
• InChiKey: AQJXMQKMZQIXPK-LPHOPBHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  47.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4R)-1-benzyl-4-(3,4-difluorophenyl)-4-hydroxypiperidine-3-carbonitrile 在 乙醇 、 20 % Pd(OH)2/C 、 氢气 、 双氧水 、 三乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 potassium hydroxide 、 lithium hydroxide 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 22.0~80.0 ℃ 、1.38 MPa 条件下， 反应 12.0h， 生成 tert-butyl (3S,4R)-3-{[[2-chloro-5-(2-methoxyethyl)benzyl](cyclopropyl)amino]carbonyl}-4-(3,4-difluorophenyl)-4-hydroxypiperidine-1-carboxylate
  参考文献：
  名称：

  Renin inhibitors for the treatment of hypertension: Design and optimization of a novel series of tertiary alcohol-bearing piperidines

  摘要：

  The design and optimization of a novel series of renin inhibitor is described herein. Strategically, by committing the necessary resources to the development of synthetic sequences and scaffolds that were most amenable for late stage structural diversification, even as the focus of the SAR campaign moved from one end of the molecule to another, highly potent renin inhibitors could be rapidly identified and profiled. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.014
• 作为产物：
  描述：

  3-chloro-1-(3,4-difluorophenyl)propan-1-one 在 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 、 (3R,4R)-1-benzyl-4-(3,4-difluorophenyl)-4-hydroxypiperidine-3-carbonitrile
  参考文献：
  名称：

  Renin inhibitors for the treatment of hypertension: Design and optimization of a novel series of tertiary alcohol-bearing piperidines

  摘要：

  The design and optimization of a novel series of renin inhibitor is described herein. Strategically, by committing the necessary resources to the development of synthetic sequences and scaffolds that were most amenable for late stage structural diversification, even as the focus of the SAR campaign moved from one end of the molecule to another, highly potent renin inhibitors could be rapidly identified and profiled. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.014

文献信息

• RENIN INHIBITORS
  申请人：McKay Daniel J.

  公开号：US20120035214A1

  公开（公告）日：2012-02-09

  The present invention relates to biaryl piperidine-based renin inhibitor compounds, and their use in treating cardiovascular events and renal insufficiency.

  本发明涉及基于联苯哌啶的肾素抑制剂化合物及其在治疗心血管事件和肾功能不全中的应用。
• Renin inhibitors for the treatment of hypertension: Design and optimization of a novel series of tertiary alcohol-bearing piperidines
  作者：Austin Chen、Elizabeth Cauchon、Amandine Chefson、Sarah Dolman、Yves Ducharme、Daniel Dubé、Jean-Pierre Falgueyret、Pierre-André Fournier、Sébastien Gagné、Michel Gallant、Erich Grimm、Yongxin Han、Robert Houle、Jing-Qi Huang、Gregory Hughes、Hélène Jûteau、Patrick Lacombe、Sophie Lauzon、Jean-François Lévesque、Susana Liu、Dwight MacDonald、Bruce Mackay、Dan McKay、M. David Percival、René St-Jacques、Sylvie Toulmond

  DOI：10.1016/j.bmcl.2011.05.014

  日期：2011.7

  The design and optimization of a novel series of renin inhibitor is described herein. Strategically, by committing the necessary resources to the development of synthetic sequences and scaffolds that were most amenable for late stage structural diversification, even as the focus of the SAR campaign moved from one end of the molecule to another, highly potent renin inhibitors could be rapidly identified and profiled. (C) 2011 Elsevier Ltd. All rights reserved.