4-((3,5-bis(trifluoro-methyl)benzyloxy)methyl)-4-phenylpiperidin-2-one | 1429045-44-2

• 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: 4-((3,5-bis(trifluoro-methyl)benzyloxy)methyl)-4-phenylpiperidin-2-one
• 英文别名: 4-[[3,5-Bis(trifluoromethyl)phenyl]methoxymethyl]-4-phenylpiperidin-2-one；4-[[3,5-bis(trifluoromethyl)phenyl]methoxymethyl]-4-phenylpiperidin-2-one
• CAS: 1429045-44-2
• 化学式: C₂₁H₁₉F₆NO₂
• 分子量: 431.378
• InChiKey: HBDJTAXFKXXUNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl 2-allyl-2-phenylpent-4-enoate 在 Grubbs catalyst first generation 、 lithium aluminium tetrahydride 、 sodium azide 、 硼烷四氢呋喃络合物 、 sodium hydride 、 pyridinium chlorochromate 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 、 苯 为溶剂， 反应 16.5h， 生成 5-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-5-phenylpiperidin-2-one 、 4-((3,5-bis(trifluoro-methyl)benzyloxy)methyl)-4-phenylpiperidin-2-one
  参考文献：
  名称：

  Discovery of disubstituted piperidines and homopiperidines as potent dual NK 1 receptor antagonists–serotonin reuptake transporter inhibitors for the treatment of depression

  摘要：

  This report describes the synthesis, structure-activity relationships and activity of piperidine, homopiperidine, and azocane derivatives combining NK1 receptor (NK1R) antagonism and serotonin reuptake transporter (SERT) inhibition. Our studies culminated in the discovery of piperidine 2 and homopiperidine 8 as potent dual NK1R antagonists-SERT inhibitors. Compound 2 demonstrated significant activity in the gerbil forced swimming test, suggesting that dual NK1R antagonists-SERT inhibitors may be useful in treating depression disorders. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.010

文献信息

• Discovery of disubstituted piperidines and homopiperidines as potent dual NK 1 receptor antagonists–serotonin reuptake transporter inhibitors for the treatment of depression
  作者：Yong-Jin Wu、Huan He、Robert Bertekap、Ryan Westphal、Snjezana Lelas、Amy Newton、Tanya Wallace、Matthew Taber、Carl Davis、John E. Macor、Joanne Bronson

  DOI：10.1016/j.bmc.2013.02.010

  日期：2013.4

  This report describes the synthesis, structure-activity relationships and activity of piperidine, homopiperidine, and azocane derivatives combining NK1 receptor (NK1R) antagonism and serotonin reuptake transporter (SERT) inhibition. Our studies culminated in the discovery of piperidine 2 and homopiperidine 8 as potent dual NK1R antagonists-SERT inhibitors. Compound 2 demonstrated significant activity in the gerbil forced swimming test, suggesting that dual NK1R antagonists-SERT inhibitors may be useful in treating depression disorders. (C) 2013 Elsevier Ltd. All rights reserved.