N-benzyl-piperidin-4-ylidenemalononitrile | 616897-44-0

• 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-benzyl-piperidin-4-ylidenemalononitrile
• 英文别名: 2-(1-benzylpiperidin-4-ylidene)malononitrile；2-(1-Benzylpiperidin-4-ylidene)propanedinitrile
• CAS: 616897-44-0
• 化学式: C₁₅H₁₅N₃
• 分子量: 237.304
• InChiKey: MQWNGAQPEAZVJA-UHFFFAOYSA-N

物化性质

• 沸点：
  409.7±30.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyl-piperidin-4-ylidenemalononitrile 在 盐酸 、 sodium tetrahydroborate 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(1-苄基-4-哌啶)乙腈
  参考文献：
  名称：

  Novel coumarin-3-carboxamides bearing N-benzylpiperidine moiety as potent acetylcholinesterase inhibitors

  摘要：

  Some novel coumarin-3-carboxamide derivatives linked to N-benzylpiperidine scaffold were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors. The screening results showed that most of compounds exhibited potent anti-AChE activity in the range of nM concentrations. Among them, compound 10c bearing an N-ethylcarboxamide linker and a 6-nitro substituent showed the most potent activity (IC50 = 0.3 nM) and the highest selectivity (SI = 26,300). Compound 10c was 46-fold more potent than standard drug donepezil against AChE. The kinetic study revealed that compound 10c exhibited mixed-type inhibition against AChE. Protein-ligand docking study demonstrated that the target compounds have dual binding site interaction mode and these results are in agreement with kinetic study. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.024
• 作为产物：
  描述：

  N-苄基哌啶酮 、 丙二腈 生成 N-benzyl-piperidin-4-ylidenemalononitrile
  参考文献：
  名称：

  Functional Group Interconversion of Alkylidenemalononitriles to Primary Alcohols by a Cooperative Redox Operation

  摘要：

  功能团互变是实现合成的基本化学过程。在这份报告中，我们描述了一种将烯基丙二腈转化为一步制备的初级醇的策略。该反应依赖于经过精心设计的氧化还原过程，涉及烯基丙烯还原、丙二腈氧化和酰氰还原，其中分子氧和NaBH4共同发挥作用。这种方法已应用于各种碳骨架，并用于合成复杂的萜类结构。

  DOI：

  10.1055/s-0040-1707184

文献信息

• Synthesis of Some New 4-Substituted<i>N</i>-Benzyl-piperidines
  作者：Gábor Dörnyei、Mária Incze、István Moldvai、Csaba Szántay

  DOI：10.1081/scc-120021515

  日期：2003.1.7

  Via Knoevenagel condensation of N-benzyl-4-piperidone with malononitrile some new 4-substituted N-benzyl-piperidines have been prepared. By means of these transformations an economic and large-scale synthesis of biologically important intermediate N-benzyl-piperidine-4-ethanol has been elaborated.
• Synthesis and evaluation of tacrine–E2020 hybrids as acetylcholinesterase inhibitors for the treatment of Alzheimer’s disease
  作者：Dong Shao、Chunyan Zou、Cheng Luo、Xican Tang、Yuanchao Li

  DOI：10.1016/j.bmcl.2004.07.005

  日期：2004.9

  Tacrine-E2020 hybrids and some related compounds were prepared and their bioactivities on the Alzheimer's disease were assayed. The optimum hybrid inhibitor 3 is 37-fold more potent and 31-fold more selective than tacrine in vitro. (C) 2004 Elsevier Ltd. All rights reserved.
• Novel coumarin-3-carboxamides bearing N-benzylpiperidine moiety as potent acetylcholinesterase inhibitors
  作者：Ali Asadipour、Masoumeh Alipour、Mona Jafari、Mehdi Khoobi、Saeed Emami、Hamid Nadri、Amirhossein Sakhteman、Alireza Moradi、Vahid Sheibani、Farshad Homayouni Moghadam、Abbas Shafiee、Alireza Foroumadi

  DOI：10.1016/j.ejmech.2013.10.024

  日期：2013.12

  Some novel coumarin-3-carboxamide derivatives linked to N-benzylpiperidine scaffold were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors. The screening results showed that most of compounds exhibited potent anti-AChE activity in the range of nM concentrations. Among them, compound 10c bearing an N-ethylcarboxamide linker and a 6-nitro substituent showed the most potent activity (IC50 = 0.3 nM) and the highest selectivity (SI = 26,300). Compound 10c was 46-fold more potent than standard drug donepezil against AChE. The kinetic study revealed that compound 10c exhibited mixed-type inhibition against AChE. Protein-ligand docking study demonstrated that the target compounds have dual binding site interaction mode and these results are in agreement with kinetic study. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Functional Group Interconversion of Alkylidenemalononitriles to Primary Alcohols by a Cooperative Redox Operation
  作者：Alexander J. Grenning、Fabien Emmetiere

  DOI：10.1055/s-0040-1707184

  日期：——

  Functional group interconversions are essential chemical processes enabling synthesis. In this report, we describe a strategy to convert alkylidenemalononitriles into primary alcohols in one step. The reaction relies on a choreographed redox process involving alkylidene reduction, malononitrile oxidation, and acylcyanide reduction where molecular oxygen and NaBH4 work cooperatively. The method was applied to a variety of carbon skeletons and was utilized to synthesize complex terpenoid architectures.

  功能团互变是实现合成的基本化学过程。在这份报告中，我们描述了一种将烯基丙二腈转化为一步制备的初级醇的策略。该反应依赖于经过精心设计的氧化还原过程，涉及烯基丙烯还原、丙二腈氧化和酰氰还原，其中分子氧和NaBH4共同发挥作用。这种方法已应用于各种碳骨架，并用于合成复杂的萜类结构。