3-(4-(trifluoromethyl)phenyl)pyridine 1-oxide | 426823-30-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(4-(trifluoromethyl)phenyl)pyridine 1-oxide
• 英文别名: 3-(4-Trifluoromethylphenyl)pyridine 1-oxide；1-oxido-3-[4-(trifluoromethyl)phenyl]pyridin-1-ium
• CAS: 426823-30-5
• 化学式: C₁₂H₈F₃NO
• 分子量: 239.197
• InChiKey: XWAVRVGNYMCQDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  25.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-(trifluoromethyl)phenyl)pyridine 1-oxide 在 乙酸酐 作用下， 生成 2-Hydroxy-3-(4-trifluoromethylphenyl)pyridine
  参考文献：
  名称：

  3-Aryl pyridone derivatives. Potent and selective kappa opioid receptor agonists

  摘要：

  A new series of 3-aryl pyridone based kappa opioid receptor agonists was designed and synthesised, based on an understanding of the classical kappa opioid receptor pharmacophore. The most potent of the new compounds were comparable to U-69,593 in receptor affinity, selectivity and functional agonist effect at the cloned human kappa opioid receptor. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00691-6
• 作为产物：
  描述：

  3-[4-(三氟甲基）苯基]吡啶 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以387 mg的产率得到3-(4-(trifluoromethyl)phenyl)pyridine 1-oxide
  参考文献：
  名称：

  氮杂芳烃 N-氧化物的 N-氧化物到碳的转变

  摘要：

  改变环系统内原子特性的反应正在成为分子结构位点选择性编辑的有价值的工具。在此，我们描述了一种不发达的转化的扩展，该转化直接将氮杂芳烃衍生的N-氧化物转化为全碳芳烃。这种环嬗变表现出良好的官能团耐受性，并在一次实验室操作中用未取代、取代或同位素标记的碳原子取代N-氧化物部分。

  DOI：

  10.1021/acs.orglett.4c01263

文献信息

• Novel pyridinone and related heterocyclic derivatives
  申请人：——

  公开号：US20040186104A1

  公开（公告）日：2004-09-23

  The present invention relates to a compound of formula (1), (2) or (3) having the following structures: Formula 1, 2, 3 wherein X, Y, and Z are independently C or N; A is a direct bond, CH2 or NH;B is a direct bond or NH; n=0-2; R1 is H, optionally substituted C 1-4 191 alkyl, C 3-7 191 cycloalkyl, halogen, cyano, nitro, aryl, or alkylaryl; R2 is H, C 1-4 191 alkyl, or alkoxy C 1-4 191 alkyl;or R1 and R2 are taken together to form an unsaturated 6-membered aromatic or heterocyclic ring containing one or two heteroatoms fused to the pyridone; R3 is a direct bond, H, C 1-4 191 alkyl, substituted C 1-4 191 alkyl, C 3-7 191 cycloalkyl, aryl or alkylaryl; R4 is a direct bond or H; R5 is C 1-4 191 alkyl or aryl; R6 and R7 are independently H or C 1-4 191 alkyl; R8 and R9 are independently H, C 1-4 191 alkyl, or tert-butoxycarbonyl or R8 and R9 are taken together with the nitrogen to which they are attached and form optionally, unsubstituted, substituted, fused or unsaturated 5-,6-,7-membered heterocycles containing one or two heteroatoms wherein said substituents are selected from the group consisting of hydroxyl, hydroxymethyl, carboxymethyl, carboxy, methoxy, and tert-butoxy;as (R)enantiomers, (S)-enantiomers or a racemate in the form of a free base or a pharmaceutically acceptable salt or solvate thereof. 1

  本发明涉及具有以下结构的式（1），（2）或（3）的化合物：式1，2，3，其中X，Y和Z独立地为C或N；A为直接键，CH2或NH；B为直接键或NH；n＝0-2；R1为H，可选地取代的C1-4191烷基，C3-7191环烷基，卤素，氰基，硝基，芳基或烷基芳基；R2为H，C1-4191烷基或烷氧基C1-4191烷基；或R1和R2一起形成不饱和的6元芳香或杂环环，其中包含一个或两个杂原子与吡啶酮融合；R3为直接键，H，C1-4191烷基，取代的C1-4191烷基，C3-7191环烷基，芳基或烷基芳基；R4为直接键或H；R5为C1-4191烷基或芳基；R6和R7独立地为H或C1-4191烷基；R8和R9独立地为H，C1-4191烷基或叔丁氧羰基或R8和R9与它们连接的氮一起形成可选地未取代，取代，融合或不饱和的5、6、7元杂环，其中所述取代基从羟基，羟甲基，羧甲基，羧基，甲氧基和叔丁氧基的群中选择；作为（R）对映体，（S）-对映体或自由碱形式或药学上可接受的盐或溶剂的混合物。
• NOVEL PYRIDINONE AND RELATED HETEROCYCLIC DERIVATIVES
  申请人：AstraZeneca AB

  公开号：EP1387829A1

  公开（公告）日：2004-02-11
• [EN] NOVEL PYRIDINONE AND RELATED HETEROCYCLIC DERIVATIVES<br/>[FR] PYRIDINONE ET DERIVES HETEROCYCLIQUES CONNEXES
  申请人：ASTRAZENECA AB

  公开号：WO2002090333A1

  公开（公告）日：2002-11-14

  The present invention relates to a compound of formula (1), (2) or (3) having the following structures: Formula 1, 2, 3 wherein X, Y, and Z are independently C or N; A is a direct bond, CH2 or NH;B is a direct bond or NH; n= 0-2; R1 is H, optionally substituted C1-4191 alkyl, C3-7191 cycloalkyl, halogen, cyano, nitro, aryl, or alkylaryl; R2 is H, C1-4191 alkyl, or alkoxy C1-4191 alkyl;or R1 and R2 are taken together to form an unsaturated 6-membered aromatic or heterocyclic ring containing one or two heteroatoms fused to the pyridone; R3 is a direct bond, H, C1-4191 alkyl, substituted C1-4191 alkyl, C3-7191 cycloalkyl, aryl or alkylaryl; R4 is a direct bond or H; R5 is C1-4191 alkyl or aryl; R6 and R7 are independently H or C1-4191 alkyl; R8 and R9 are independently H, C1-4191 alkyl, or tert-butoxycarbonyl or R8 and R9 are taken together with the nitrogen to which they are attached and form optionally, unsubstituted, substituted, fused or unsaturated 5-,6-,7-membered heterocycles containing one or two heteroatoms wherein said substituents are selected from the group consisting of hydroxyl, hydroxymethyl, carboxymethyl, carboxy, methoxy, and tert-butoxy;as (R)-enantiomers, (S)-enantiomers or a racemate in the form of a free base or a pharmaceutically acceptable salt or solvate thereof.
• 3-Aryl pyridone derivatives. Potent and selective kappa opioid receptor agonists
  作者：Graeme Semple、Britt-Marie Andersson、Vijay Chhajlani、Jennie Georgsson、Magnus Johansson、Marcel Lindschoten、Fritof Pontén、Åsa Rosenquist、Henrik Sörensen、Lars Swanson、Marianne Swanson

  DOI：10.1016/s0960-894x(01)00691-6

  日期：2002.1

  A new series of 3-aryl pyridone based kappa opioid receptor agonists was designed and synthesised, based on an understanding of the classical kappa opioid receptor pharmacophore. The most potent of the new compounds were comparable to U-69,593 in receptor affinity, selectivity and functional agonist effect at the cloned human kappa opioid receptor. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 10.1021/acs.orglett.4c01263
  作者：Falcone, Nicholas A.、He, Sam、Hoskin, John F.、Mangat, Sandeep、Sorensen, Erik J.

  DOI：10.1021/acs.orglett.4c01263

  日期：——

  editing of molecular structures. Herein, we describe the expansion of an underdeveloped transformation that directly converts azaarene-derived N-oxides to all-carbon arenes. This ring transmutation exhibits good functional group tolerance and replaces the N-oxide moiety with either unsubstituted, substituted, or isotopically labeled carbon atoms in a single laboratory operation.

  改变环系统内原子特性的反应正在成为分子结构位点选择性编辑的有价值的工具。在此，我们描述了一种不发达的转化的扩展，该转化直接将氮杂芳烃衍生的N-氧化物转化为全碳芳烃。这种环嬗变表现出良好的官能团耐受性，并在一次实验室操作中用未取代、取代或同位素标记的碳原子取代N-氧化物部分。