1-phenylazo-4-piperidone

• 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: 1-phenylazo-4-piperidone
• 化学式: C₁₁H₁₃N₃O
• 分子量: 203.244
• InChiKey: CCGGFXOHAOGZHJ-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  45.03
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-phenylazo-4-piperidone 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 phenyl(piperidin-1-yl)diazene
  参考文献：
  名称：

  Triazenes: A Useful Protecting Strategy for Sensitive Secondary Amines

  摘要：

  DOI：

  10.1055/s-1999-2803
• 作为产物：
  描述：

  1-phenylazo-4-hydroxypiperidine 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到1-phenylazo-4-piperidone
  参考文献：
  名称：

  Application of triazenes for protection of secondary amines

  摘要：

  Use of the phenyldiazenyl group, which serves as a protecting group for secondary amines is described in detail. The triazene protected amine is compatible with oxidative and reductive conditions as well as with strong bases (LDA, tert-butyllithium) and alkylating reagents. The amine is regenerated by action of trifluoroacetic acid and a suitable reducing agent (EtOH or NaH2PO2). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00495-1

文献信息

• Photochromic Fentanyl Derivatives for Controlled μ‐Opioid Receptor Activation
  作者：Ranit Lahmy、Harald Hübner、Maximilian F. Schmidt、Daniel Lachmann、Peter Gmeiner、Burkhard König

  DOI：10.1002/chem.202201515

  日期：2022.11.11

  Photoresponsive fentanyl-based ligands provide the opportunity to spatially, temporally, and non-invasively regulate μ-opioid receptor activity by using light. The repertoire of such ligands has been expanded in this work, yielding a desirable selection that differ in photophysical properties and/or metabotropic response.

  基于光响应芬太尼的配体提供了通过使用光在空间上、时间上和非侵入性地调节μ-阿片受体活性的机会。此类配体的所有成分在这项工作中得到了扩展，产生了光物理特性和/或代谢反应不同的理想选择。
• Triazenes: A Useful Protecting Strategy for Sensitive Secondary Amines
  作者：Ryszard Lazny、Janusz Poplawski、Johannes Köbberling、Dieter Enders、Stefan Bräse

  DOI：10.1055/s-1999-2803

  日期：1999.8
• Application of triazenes for protection of secondary amines
  作者：Ryszard Lazny、Michal Sienkiewicz、Stefan Bräse

  DOI：10.1016/s0040-4020(01)00495-1

  日期：2001.7

  Use of the phenyldiazenyl group, which serves as a protecting group for secondary amines is described in detail. The triazene protected amine is compatible with oxidative and reductive conditions as well as with strong bases (LDA, tert-butyllithium) and alkylating reagents. The amine is regenerated by action of trifluoroacetic acid and a suitable reducing agent (EtOH or NaH2PO2). (C) 2001 Elsevier Science Ltd. All rights reserved.