(6S)-6-[[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]methyl]-6-phenylpiperidin-2-one | 530440-10-9

• 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: (6S)-6-[[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]methyl]-6-phenylpiperidin-2-one
• CAS: 530440-10-9
• 化学式: C₂₂H₂₁F₆NO₂
• 分子量: 445.405
• InChiKey: PGGJJCALJAQHKK-JLTOFOAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (6S)-6-[[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]methyl]-6-phenylpiperidin-2-one 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以56%的产率得到(S)-2-(((R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)methyl)-2-phenylpiperidine
  参考文献：
  名称：

  Two complementary, diversity-driven asymmetric syntheses of a 2,2-disubstituted piperidine NK1 antagonist

  摘要：

  Two diversity-driven asymmetric syntheses of a potent NK1 receptor antagonist I were achieved. These syntheses provided two complementary approaches that were well positioned for further modifications of several different sites of medicinal chemistry interests in the NK1 structural motifs. The de novo piperidine ring construction approach delivered key intermediates that were best suited for piperidine C4 and C5 SAR investigations. The CNRS method fit well for modifications at C6 and the two exocyclic groups. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.09.022
• 作为产物：
  描述：

  2-{(1R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy}-1-phenylethan-1-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium on activated charcoal titanium(IV) isopropylate 、 盐酸 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 (6S)-6-[[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]methyl]-6-phenylpiperidin-2-one
  参考文献：
  名称：

  Two complementary, diversity-driven asymmetric syntheses of a 2,2-disubstituted piperidine NK1 antagonist

  摘要：

  Two diversity-driven asymmetric syntheses of a potent NK1 receptor antagonist I were achieved. These syntheses provided two complementary approaches that were well positioned for further modifications of several different sites of medicinal chemistry interests in the NK1 structural motifs. The de novo piperidine ring construction approach delivered key intermediates that were best suited for piperidine C4 and C5 SAR investigations. The CNRS method fit well for modifications at C6 and the two exocyclic groups. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.09.022

文献信息

• NK1 ANTAGONISTS
  申请人：Schering Corporation

  公开号：EP1451153B1

  公开（公告）日：2007-09-26
• Two complementary, diversity-driven asymmetric syntheses of a 2,2-disubstituted piperidine NK1 antagonist
  作者：Dong Xiao、Cheng Wang、Anandan Palani、Gregory Reichard、Robert Aslanian、Neng-Yang Shih、Alexei Buevich

  DOI：10.1016/j.tetasy.2006.09.022

  日期：2006.10

  Two diversity-driven asymmetric syntheses of a potent NK1 receptor antagonist I were achieved. These syntheses provided two complementary approaches that were well positioned for further modifications of several different sites of medicinal chemistry interests in the NK1 structural motifs. The de novo piperidine ring construction approach delivered key intermediates that were best suited for piperidine C4 and C5 SAR investigations. The CNRS method fit well for modifications at C6 and the two exocyclic groups. (c) 2006 Elsevier Ltd. All rights reserved.