1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine | 6755-56-2

• 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: 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
• 英文别名: 1-methyl-5-phenyl-1,2,3,6-tetrahydropyridine；1-Methyl-3-phenyl-1,2,5,6-tetrahydro-pyridin；1-methyl-3-phenyl-1,2,5,6-tetrahydropyridine；Pyridine, 1,2,3,6-tetrahydro-1-methyl-5-phenyl-；1-methyl-5-phenyl-3,6-dihydro-2H-pyridine
• CAS: 6755-56-2
• 化学式: C₁₂H₁₅N
• 分子量: 173.258
• InChiKey: QKROHGALCSHSER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine 在 monoamine oxidase whole cell variant D₉ 作用下， 以 异辛烷 为溶剂， 反应 24.0h， 生成 1-methyl-3-phenylpyridinium
  参考文献：
  名称：

  Monoamine Oxidase (MAO-N) Whole Cell Biocatalyzed Aromatization of 1,2,5,6-Tetrahydropyridines into Pyridines

  摘要：

  A sustainable MAO-N biocatalyzed process for the synthesis of pyridines from aliphatic tetrahydropyridines (THP) has been developed. Pyridine compounds were synthesized under mild reaction conditions and with high conversion, exploiting MAO-N whole cells as aromatizing biocatalysts. The kinetic profile of the whole cell biocatalytic transformation was finally investigated via in situ F-19 NMR.

  DOI：

  10.1021/acscatal.8b02386
• 作为产物：
  描述：

  1-methyl-3-phenylpyridinium iodide 在 四羟基二硼 、 potassium tert-butylate 、 水 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以70%的产率得到1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
  参考文献：
  名称：

  用四羟基二硼/水对不饱和羰基、醌和吡啶鎓盐进行无金属还原

  摘要：

  一系列不饱和羰基、醌和吡啶盐已被有效地还原为相应的饱和羰基、二羟基苯和氢吡啶，其中四羟基二硼/水是一种温和、方便且无金属的还原体系，其产率中等至高。氘标记实验表明，该协议是一种从水中进行的独家转移氢化过程。

  DOI：

  10.1039/d1ob00300c

文献信息

• Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water
  作者：Henian Peng、Tiejun Li、Duanshuai Tian、He Yang、Guangqing Xu、Wenjun Tang

  DOI：10.1039/d1ob00300c

  日期：——

  A series of unsaturated carbonyls, quinones, and pyridinium salts have been effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes, and hydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient, and metal-free reduction system. Deuterium-labeling experiments have revealed this protocol to be an exclusive transfer hydrogenation process from

  一系列不饱和羰基、醌和吡啶盐已被有效地还原为相应的饱和羰基、二羟基苯和氢吡啶，其中四羟基二硼/水是一种温和、方便且无金属的还原体系，其产率中等至高。氘标记实验表明，该协议是一种从水中进行的独家转移氢化过程。
• First Efficient and General Copper-Catalyzed [2,3]-Rearrangement of Tetrahydropyridinium Ylids
  作者：Edward Roberts、Julien P. Sançon、Joseph B. Sweeney、James A. Workman

  DOI：10.1021/ol035747j

  日期：2003.12.1

  The factors affecting the copper-catalyzed rearrangement of ammonium ylids derived from tetrahydropyridines and diazoesters have been examined,and the first examples of high-yielding metal-catalyzed [2,3]-sigmatropic rearrangements of a wide range of such ylids are reported. The nature of the alpha-substituent in the diazo component of the reaction has a dramatic effect upon the yields of the reaction

  已研究了影响铜催化衍生自四氢吡啶和重氮酯的铵基重排的因素，并且报道了高产率的金属催化的[2,3]-σ重排的首例实例，这些大范围的此类基团。反应的重氮组分中的α-取代基的性质对反应的产率具有显着的影响，吸电子取代基提高了反应的产率。[反应：看文字]
• Cis- and
  申请人：Hoechst-Roussel Pharmaceuticals, Inc.

  公开号：US04382141A1

  公开（公告）日：1983-05-03

  Novel 4-aryloxy- and 4-arylthio-3-phenylpiperidines and related compounds, physiologically acceptable salts thereof and intermediates therefor possessing analgesic, antidepressant properties, and a process for the preparation of such compounds, derivatives and intermediates are described.

  本发明涉及4-芳氧基和4-芳硫基-3-苯基哌啶及其相关化合物，其生理上可接受的盐和中间体，具有镇痛、抗抑郁特性，以及制备这种化合物、衍生物和中间体的方法。
• Process for preparing 4-aryloxy-3-phenylpiperidines
  申请人：Hoechst-Roussel Pharmaceuticals, Inc.

  公开号：US04424357A1

  公开（公告）日：1984-01-03

  Novel 4-aryloxy- and 4-arylthio-3-phenylpiperidines and related compounds, physiologically acceptable salts thereof and intermediates therefor possessing analgesic, antidepressant properties, and a process for the preparation of such compounds, derivatives and intermediates are described.

  本发明涉及一种新型的4-芳氧基和4-芳硫基-3-苯基哌啶类化合物及其相关衍生物、生理学上可接受的盐和中间体，具有镇痛、抗抑郁性能，以及制备此类化合物、衍生物和中间体的方法。
• Antidepressant and analgesic 4-aryloxy- and
  申请人：American Hoechst Corporation

  公开号：US04216218A1

  公开（公告）日：1980-08-05

  Novel 4-aryloxy- and 4-arylthio-3-phenylpiperidines and related compounds, physiologically acceptable salts thereof and intermediates therefor possessing analgesic, antidepressant properties, and a process for the preparation of such compounds, derivatives and intermediates are described.

  描述了一种新型的4-芳氧基和4-芳硫基-3-苯基哌啶和相关化合物，其生理可接受的盐以及具有镇痛和抗抑郁特性的中间体，以及制备这些化合物、衍生物和中间体的方法。