1-(3-cyanobenzyl)piperidin-2-one | 936249-42-2

• 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: 1-(3-cyanobenzyl)piperidin-2-one
• 英文别名: 3-[(2-Oxo-1-piperidinyl)methyl]benzonitrile；3-[(2-oxopiperidin-1-yl)methyl]benzonitrile
• CAS: 936249-42-2
• 化学式: C₁₃H₁₄N₂O
• 分子量: 214.267
• InChiKey: QQLZDPOBJPBUQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  哌啶酮 、 3-氰基苄基溴 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以24%的产率得到1-(3-cyanobenzyl)piperidin-2-one
  参考文献：
  名称：

  Designing Active Template Molecules by Combining Computational De Novo Design and Human Chemist's Expertise

  摘要：

  We used a new software tool for de novo design, the "Molecule Evoluator", to generate a number of small molecules. Explicit constraints were a relatively low molecular weight and otherwise limited functionality, for example, low numbers of hydrogen bond donors and acceptors, one or two aromatic rings, and a small number of rotatable bonds. In this way, we obtained a collection of scaffold- or templatelike molecules rather than fully "decorated" ones. We asked medicinal chemists to evaluate the suggested molecules for ease of synthesis and overall appeal, allowing them to make structural changes to the molecules for these reasons. On the basis of their recommendations, we synthesized eight molecules with an unprecedented (not patented) yet simple structure, which were subsequently tested in a screen of 83 drug targets, mostly G protein-coupled receptors. Four compounds showed affinity for biogenic amine targets (receptor, ion channel, and transport protein), reflecting the training of the medicinal chemists involved. Apparently the generation of leadlike solutions helped the medicinal chemists to select good starting points for future lead optimization, away from existing compound libraries.

  DOI：

  10.1021/jm061356+

文献信息

• Designing Active Template Molecules by Combining Computational De Novo Design and Human Chemist's Expertise
  作者：Eric-Wubbo Lameijer、Reynier A. Tromp、Ronald F. Spanjersberg、Johannes Brussee、Adriaan P. IJzerman

  DOI：10.1021/jm061356+

  日期：2007.4.1

  We used a new software tool for de novo design, the "Molecule Evoluator", to generate a number of small molecules. Explicit constraints were a relatively low molecular weight and otherwise limited functionality, for example, low numbers of hydrogen bond donors and acceptors, one or two aromatic rings, and a small number of rotatable bonds. In this way, we obtained a collection of scaffold- or templatelike molecules rather than fully "decorated" ones. We asked medicinal chemists to evaluate the suggested molecules for ease of synthesis and overall appeal, allowing them to make structural changes to the molecules for these reasons. On the basis of their recommendations, we synthesized eight molecules with an unprecedented (not patented) yet simple structure, which were subsequently tested in a screen of 83 drug targets, mostly G protein-coupled receptors. Four compounds showed affinity for biogenic amine targets (receptor, ion channel, and transport protein), reflecting the training of the medicinal chemists involved. Apparently the generation of leadlike solutions helped the medicinal chemists to select good starting points for future lead optimization, away from existing compound libraries.