N-(3-(1,3-dioxolan-2-yl)phenyl)-1-benzylpiperidin-4-amine | 477178-66-8

• 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: N-(3-(1,3-dioxolan-2-yl)phenyl)-1-benzylpiperidin-4-amine
• 英文别名: (1-Benzyl-piperidin-4-yl)-(3-[1,3]dioxolan-2-yl-phenyl)-amine；1-benzyl-N-[3-(1,3-dioxolan-2-yl)phenyl]piperidin-4-amine
• CAS: 477178-66-8
• 化学式: C₂₁H₂₆N₂O₂
• 分子量: 338.45
• InChiKey: GJLZFIIAQNLYIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  493.7±45.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  33.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3-(1,3-dioxolan-2-yl)phenyl)-1-benzylpiperidin-4-amine 、 N,N-二乙基-4-溴苯甲酰胺 在 tris-(dibenzylideneacetone)dipalladium(0) 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 以79%的产率得到4-[N-(1-benzylpiperidin-4-yl)-3-(1,3-dioxolan-2-yl)anilino]-N,N-diethylbenzamide
  参考文献：
  名称：

  Delta agonist hydroxy bioisosteres: The discovery of 3-((1-benzylpiperidin-4-yl){4-[(diethylamino)carbonyl]phenyl}amino)benzamide with improved delta agonist activity and in vitro metabolic stability

  摘要：

  We have investigated phenol replacements in a series of diaryl amino piperidine delta opioid agonists. From this study we have demonstrated that the hydroxy functional group can be replaced with a primary amide group, giving enhanced activity at the delta receptor, increased selectivity versus mu and kappa as well as improved in vitro metabolic stability. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.068
• 作为产物：
  描述：

  2-(3-溴苯基)-1,3-二氧烷 、 4-氨基-1-苄基哌啶 在 tris-(dibenzylideneacetone)dipalladium(0) 、 5-(二环己基膦基)-1',3',5'-三苯基-[1,4']-联-1H-吡唑 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 2-甲基-2-丁醇 为溶剂， 反应 16.0h， 以50%的产率得到N-(3-(1,3-dioxolan-2-yl)phenyl)-1-benzylpiperidin-4-amine
  参考文献：
  名称：

  异丙基 BippyPhos 预催化剂的合成和表征

  摘要：

  对我们的高通量反应筛选数据的审查显示，BippyPhos 经常与 Buchwald-Hartwig 胺化反应的成功结果相关。这种配体更广泛使用的障碍，特别是在那些进行小规模工作的人中，可能是缺乏现成的预催化剂。我们描述了异丙基 BippyPhos 的多克合成和表征，以及它向异丙基 BippyPhos Pd G2（一种联芳基膦预催化剂）的转化。我们证明了异丙基 BippyPhos Pd G2 在钯催化的 Buchwald-Hartwig 胺化反应和 Suzuki-Miyaura 交叉偶联反应中的能力。

  DOI：

  10.1016/j.tet.2021.132597

文献信息

• 4-(Phenyl-(piperidin-4-yl)-amino)-benzamide derivatives and their use for the treatment of pain, anxiety or gastrointestinal disorders
  申请人：——

  公开号：US20040235897A1

  公开（公告）日：2004-11-25

  Compounds of general formula I 1 R 1 is selected from any one of phenyl, pyridinyl, pyrrolyl, thienyl, furanyl, imidazolyl, triazolyl, and pyridine N-oxide; where each R 1 phenyl ring and R 1 heteroaromatic ring may optionally and independently be further substituted by 1,2 or 3 substituents selected from straight and branched C 1 -C 6 alkyl, NO 2 , CF 3 , C 1 -C 6 alkoxy, chloro, fluoro, bromo, and iodo. The substitutions on the phenyl ring and on the heteroaromatic ring may take place in any position on said ring systems; are disclosed and claimed in the present application, as well as their pharmaceutically acceptable salts and pharmaceutical compositions comprising the novel compounds and their use in therapy, in particular in the management of pain, anxiety and functional gastrointestinal disorders.

  通式I1R1的化合物选择自苯基、吡啶基、吡咯基、噻吩基、呋喃基、咪唑基、三唑基和吡啶N-氧化物中的任意一种；其中每个R1苯环和R1杂环环可以选择性地且独立地进一步由1、2或3个取代基组成，所述取代基选择自直链和支链C1-C6烷基、NO2、CF3、C1-C6烷氧基、氯、氟、溴和碘。苯环和杂环环上的取代作用可以在所述环系统的任何位置发生；本申请公开并要求其药学上可接受的盐和含有新化合物的药物组合物以及它们在治疗中的使用，特别是在疼痛、焦虑和功能性胃肠障碍的管理中。
• 4-(phenyl-(piperidin-4yl)-amino)-benzamide derivatives and their use for the treatment of pain, anxiety or gastrointestinal disorders
  申请人：——

  公开号：US20040142965A1

  公开（公告）日：2004-07-22

  Compounds of general formula I [Chemical formula should be inserted here. Please see paper copy] R 1 is selected from any one of phenyl, pyridinyl, thienyl, furanyl, imidazolyl, pyrrolyl, triazolyl, thiazolyl, and pyridine N-oxide; where each R 1 phenyl ring and R 1 heteroaromatic ring may optionally and independently be further substituted by 1, 2 or 3 substituents selected from straight and branched C 1 -C 6 alkyl, NO 2 , CF 3 , C 1 -C 6 alkoxy, chloro, fluoro, bromo, and iodo. The substitutions on the phenyl ring and on the heteroaromatic ring may take place in any position on said ring systems; are disclosed and claimed in the present application, as well as salts and pharmaceutical compositions comprising the novel compounds and their use in therapy, in particular in the management of pain, anxiety or functional gastrointestinal disorders.

  通式I的化合物 [化学式应在此处插入。请参见纸质副本]，其中R1从苯基、吡啶基、噻吩基、呋喃基、咪唑基、吡咯基、三唑基、噻唑基和吡啶N-氧化物中选择；其中每个R1苯环和R1杂环环可以选择且独立地进一步由选自直链和支链C1-C6烷基、NO2、CF3、C1-C6烷氧基、氯、氟、溴和碘的1、2或3个取代基取代。苯环和杂环环上的取代基可以在所述环系统上的任何位置发生；本申请中披露和声明了这些取代基，以及包括新化合物的盐和药物组成物以及它们在治疗中的使用，特别是在疼痛、焦虑或功能性胃肠疾病的管理中。
• 4-(phenyl-(piperidin-4-yl)-amino)-benzamide derivatives and their use for the treatment of pain, anxiety or gastrointestinal disorders
  申请人：AstraZeneca AB

  公开号：US07226933B2

  公开（公告）日：2007-06-05

  Compounds of general formula I R1 is selected from any one of phenyl, pyridinyl, pyrrolyl, thienyl, furanyl, imidazolyl, triazolyl, and pyridine N-oxide; where each R1 phenyl ring and R1 heteroaromatic ring may optionally and independently be further substituted by 1, 2 or 3 substituents selected from straight and branched C1–C6alkyl, NO2, CF3, C1–C6alkoxy, chloro, fluoro, bromo, and iodo. The substitutions on the phenyl ring and on the heteroaromatic ring may take place in any position on said ring systems; are disclosed and claimed in the present application, as well as their pharmaceutically acceptable salts and pharmaceutical compositions comprising the novel compounds and their use in therapy, in particular in the management of pain, anxiety and functional gastrointestinal disorders.

  通式为IR1的化合物可从苯基、吡啶基、吡咯基、噻吩基、呋喃基、咪唑基、三唑基和吡啶N-氧化物中选择；其中，每个R1苯环和R1杂环环上的取代基可以选择性地独立地进一步取代为1、2或3个取代基，所选的取代基包括直链和支链C1-C6烷基、NO2、CF3、C1-C6烷氧基、氯、氟、溴和碘。苯环和杂环环上的取代作用可以在所述环系统的任何位置发生；本申请公开和声明了这些化合物及其药学上可接受的盐和包含这些新化合物的制药组合物，并且它们在治疗中的使用，特别是在疼痛、焦虑和功能性胃肠疾病的管理中。
• 4-(PHENYL-(PIPERIDIN-4-YL)-AMINO)-BENZAMIDE DERATIVATIVES AND THEIR USE FOR THE TREATMENT OF PAIN, ANXIETY OR GASTROINTESTINAL DISORDERS
  申请人：AstraZeneca AB

  公开号：EP1395555B1

  公开（公告）日：2005-12-21
• US7186733B2
  申请人：——

  公开号：US7186733B2

  公开（公告）日：2007-03-06