4-Biphenyl-4-yl-1-methyl-piperidine-4-carbonitrile

• 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: 4-Biphenyl-4-yl-1-methyl-piperidine-4-carbonitrile
• 英文别名: 1-Methyl-4-(4-phenylphenyl)piperidine-4-carbonitrile
• 化学式: C₁₉H₂₀N₂
• 分子量: 276.381
• InChiKey: NNJDUDRFZFESRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Biphenyl-4-yl-1-methyl-piperidine-4-carbonitrile 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and structure–activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands

  摘要：

  A series of benzyl esters of meperidine and normeperidine were synthesized and evaluated for binding affinity at serotonin, dopamine and norepinephrine transporters. The 4-methoxybenzyl ester 8b and 4-nitrobenzyl ester 8c in the meperidine series and 4-methoxybenzyl ester 14a in the normeperidine series exhibited low nanomolar binding affinities at the SERT (K-i values <2 nM) and high SERT selectivity (DAT/SERT > 1500 and NET/SERT > 1500). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.060
• 作为产物：
  描述：

  4-(4-chlorophenyl)-1-methylpiperidine-4-carbonitrile 、 苯硼酸 在 palladium diacetate 、 1,3-di-([N-(2,4,6-Me₃Ph)imidazolium-3-yl]Me)-2,4,6-Me₃Ph*2Cl- caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以91%的产率得到4-Biphenyl-4-yl-1-methyl-piperidine-4-carbonitrile
  参考文献：
  名称：

  钯-二亚咪唑-2-亚烷基配合物作为芳基氯化物与芳基硼酸的常规和有效Suzuki交叉偶联反应的催化剂

  摘要：

  一系列双咪唑盐的1 - 6合成和评价为前体bisimidazol -2-亚基配体与芳基氯和芳基硼酸的钯-催化的Suzuki交叉偶联反应。发现双咪唑鎓盐6优于咪唑鎓和其他双咪唑鎓盐，它们提供了使用多种底物的高产率的联芳基产物。

  DOI：

  10.1016/s0040-4039(99)02133-4

文献信息

• Synthesis and structure–activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands
  作者：Xiaobo Gu、Sari Izenwasser、Dean Wade、Amy Housman、Gerard Gulasey、Jill B. Rhoden、Christopher D. Savoie、David L. Mobley、Stacey A. Lomenzo、Mark L. Trudell

  DOI：10.1016/j.bmc.2010.09.060

  日期：2010.12

  A series of benzyl esters of meperidine and normeperidine were synthesized and evaluated for binding affinity at serotonin, dopamine and norepinephrine transporters. The 4-methoxybenzyl ester 8b and 4-nitrobenzyl ester 8c in the meperidine series and 4-methoxybenzyl ester 14a in the normeperidine series exhibited low nanomolar binding affinities at the SERT (K-i values <2 nM) and high SERT selectivity (DAT/SERT > 1500 and NET/SERT > 1500). (C) 2010 Elsevier Ltd. All rights reserved.
• Palladium-bisimidazol-2-ylidene complexes as catalysts for general and efficient Suzuki cross-coupling reactions of aryl chlorides with arylboronic acids
  作者：Chunming Zhang、Mark L Trudell

  DOI：10.1016/s0040-4039(99)02133-4

  日期：2000.1

  A series of bisimidazolium salts 1–6 were synthesized and evaluated as precursors to bisimidazol-2-ylidene ligands in palladium-catalyzed Suzuki cross-coupling reactions with aryl chlorides and arylboronic acids. The bisimidazolium salt 6 was found to be superior over imidazolium and other bisimidazolium salts affording high yields of biaryl products employing a wide variety of substrates.

  一系列双咪唑盐的1 - 6合成和评价为前体bisimidazol -2-亚基配体与芳基氯和芳基硼酸的钯-催化的Suzuki交叉偶联反应。发现双咪唑鎓盐6优于咪唑鎓和其他双咪唑鎓盐，它们提供了使用多种底物的高产率的联芳基产物。