methyl N-benzyl-piperidin-4-yl-cyanoacetate | 743417-80-3

• 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: methyl N-benzyl-piperidin-4-yl-cyanoacetate
• 英文别名: Methyl 2-(1-benzylpiperidin-4-yl)-2-cyanoacetate
• CAS: 743417-80-3
• 化学式: C₁₆H₂₀N₂O₂
• 分子量: 272.347
• InChiKey: XVLAAVLBNRRPCQ-UHFFFAOYSA-N

物化性质

• 沸点：
  403.7±20.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl N-benzyl-piperidin-4-yl-cyanoacetate 在 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：

  Synthesis and evaluation of tacrine–E2020 hybrids as acetylcholinesterase inhibitors for the treatment of Alzheimer’s disease

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2004.07.005
• 作为产物：
  描述：

  2-(1-苄基哌啶-4-基)丙二腈 在 盐酸 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 methyl N-benzyl-piperidin-4-yl-cyanoacetate
  参考文献：
  名称：

  Synthesis of Some New 4-SubstitutedN-Benzyl-piperidines

  摘要：

  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.

  DOI：

  10.1081/scc-120021515

文献信息

• Chemoselective Reduction of α-Cyano Carbonyl Compounds: Application to the Preparation of Heterocycles
  作者：Scott R. Pollack、Jeffrey T. Kuethe

  DOI：10.1021/acs.orglett.6b03285

  日期：2016.12.16

  in synthesis. General methods for their preparation typically afford α and β disubstitution patterns or β only. Molecules with only α-substituents (β-hydrogen) are much less well-known. A chemoselective reductive tautomerization of α-cyanoacetates, using DIBAL-H, has been developed to access these valuable synthons. α,β-Unsaturated cyanoacetates and α-cyanoketones can, also, be selectively reduced via

  β-氨基丙烯酸酯是反应性中间体，是合成中有用的组成部分。制备它们的通用方法通常仅提供α和β破坏模式或仅提供β。仅具有α-取代基（β-氢）的分子是众所周知的。已经开发出使用DIBAL-H进行α-氰基乙酸酯化学选择性还原互变异构的方法，以获取这些有价值的合成子。也可以通过该方法选择性地还原α，β-不饱和氰基乙酸酯和α-氰基酮。使用这些β-烯氨基羰基化合物制备了一系列杂环。
• 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.