哌啶,1-(苯基甲基)-4-(3-苯基丙基)- | 154746-91-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 哌啶,1-(苯基甲基)-4-(3-苯基丙基)-
• 英文名称: benzyl-4-(3-phenylpropyl)piperidine
• 英文别名: 1-Benzyl-4-(3-phenylpropyl)piperidine
• CAS: 154746-91-5
• 化学式: C₂₁H₂₇N
• 分子量: 293.452
• InChiKey: GLLAPAGUDGWOHN-UHFFFAOYSA-N

物化性质

• 沸点：
  402.8±14.0 °C(Predicted)
• 密度：
  1.009±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  哌啶,1-(苯基甲基)-4-(3-苯基丙基)- 在 chromium(VI) oxide 、 硫酸 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 1-(1-benzylpiperidin-4-yl)-2-formyl-3-phenyl-1-propanone
  参考文献：
  名称：

  Antagonists of human CCR5 receptor containing 4-(pyrazolyl)piperidine side chains. Part 1: Discovery and SAR study of 4-pyrazolylpiperidine side chains

  摘要：

  Replacement of the flexible connecting chains between the piperidine moiety and an aromatic group in previous CCR5 antagonists with heterocycles, such as pyrazole and isoxazole, provided potent CCR5 antagonists with excellent anti-HIV-1 activity in vitro. SAR studies revealed optimal placement of an unsubstituted nitrogen atom in the heterocycle to be meta to the bond connected to the 4-position of piperidine. Truncation of a benzyl group to a phenyl group afforded compounds with dramatically improved oral bioavailability, albeit with reduced activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.004
• 作为产物：
  描述：

  1-溴-3-苯基丙烷 在 硼烷 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 哌啶,1-(苯基甲基)-4-(3-苯基丙基)-
  参考文献：
  名称：

  Antagonists of human CCR5 receptor containing 4-(pyrazolyl)piperidine side chains. Part 1: Discovery and SAR study of 4-pyrazolylpiperidine side chains

  摘要：

  Replacement of the flexible connecting chains between the piperidine moiety and an aromatic group in previous CCR5 antagonists with heterocycles, such as pyrazole and isoxazole, provided potent CCR5 antagonists with excellent anti-HIV-1 activity in vitro. SAR studies revealed optimal placement of an unsubstituted nitrogen atom in the heterocycle to be meta to the bond connected to the 4-position of piperidine. Truncation of a benzyl group to a phenyl group afforded compounds with dramatically improved oral bioavailability, albeit with reduced activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.004

文献信息

• [EN] CHEMOKINE CXCR4 AND CCR5 RECEPTOR MODULATORS AND USED RELATED THERETO<br/>[FR] MODULATEURS DES RÉCEPTEURS CCR5 ET CXCR4 DE LA CHIMIOKINE ET ET LEURS UTILISATIONS
  申请人：UNIV EMORY

  公开号：WO2015175855A1

  公开（公告）日：2015-11-19

  The disclosure relates to chemokine receptor modulators and uses related thereto. In certain embodiments, the disclosure relates to pharmaceutical compositions comprising compounds disclosed herein or pharmaceutically acceptable salts or prodrugs thereof. In certain embodiments, the compositions disclosed herein are used for managing chemokine related conditions, typically prevention or treatment of viral infections such as HIV or for managing cancer.

  本公开涉及趋化因子受体调节剂及其相关用途。在某些实施例中，本公开涉及包括本公开披露的化合物或其药用盐或前药的制药组合物。在某些实施例中，本公开披露的组合物用于管理与趋化因子相关的疾病，通常是预防或治疗病毒感染如HIV或管理癌症。
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  作者：Curren T. Mbofana、Eugene Chong、James Lawniczak、Melanie S. Sanford

  DOI：10.1021/acs.orglett.6b02003

  日期：2016.9.2

  iron-catalyzed method for the selective oxyfunctionalization of benzylic C(sp3)–H bonds in aliphatic amine substrates. This transformation is selective for benzylic C–H bonds that are remote (i.e., at least three carbons) from the amine functional group. High site selectivity is achieved by in situ protonation of the amine with trifluoroacetic acid, which deactivates more traditionally reactive C–H sites that are

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  DOI：10.1002/anie.202115467

  日期：2022.2.14

  AbstractA protocol for the modular assembly of the α‐fluoroamide motif has been developed, which provides a practical method for the efficient synthesis of structurally diverse α‐fluoroamides from easily available aldehydes and tertiary amines through a three‐component fluorination–aminocarbonylation process. The key to the success of this process is taking advantage of the multiple roles of the unique difluorocarbene reagent TMSCF2Br (TMS=trimethylsilyl). The mechanism of the process involves the 1,2‐fluorine and oxygen migrations of the in situ formed TMS‐protected α‐aminodifluoromethyl carbinol intermediates, which represents a new type of deoxyfluorination reaction.
• CHEMOKINE CXCR4 AND CCR5 RECEPTOR MODULATORS AND USED RELATED THERETO
  申请人：Emory University

  公开号：EP3143005A1

  公开（公告）日：2017-03-22