1-(4-Benzylpiperidin-1-yl)-3-phenoxypropan-2-ol

• 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-(4-Benzylpiperidin-1-yl)-3-phenoxypropan-2-ol
• 化学式: C₂₁H₂₇NO₂
• 分子量: 325.451
• InChiKey: IRCVGKKVEJXPLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯酚 在 chiral polymer-supported Co(salen) complex 高氟叔丁醇 、 ytterbium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 1-(4-Benzylpiperidin-1-yl)-3-phenoxypropan-2-ol
  参考文献：
  名称：

  Enantioselective Parallel Synthesis Using Polymer-Supported Chiral Co(salen) Complexes

  摘要：

  [GRAPHICS]The kinetic resolution of epoxides with phenols catalyzed by a polymer supported Co(salen) complex is applied to the first enantioselective catalytic synthesis of parallel libraries, The corresponding 1-aryloxy-2-alcohols are obtained in high yield, purity, and enantiomeric excess. Further elaboration with diversity elements provides highly efficient access to important classes of pharmacologically active compounds.

  DOI：

  10.1021/ol990920q

文献信息

• Discovery of selective dopamine D4 receptor antagonists: 1-Aryloxy-3-(4-aryloxypiperidinyl)-2-propanols
  作者：Jon L. Wright、Tracy F. Gregory、Thomas G. Heffner、Robert G. MacKenzie、Thomas A. Pugsley、Seth Vander Meulen、Lawrence D. Wise

  DOI：10.1016/s0960-894x(97)00233-3

  日期：1997.6

  High volume screening identified 3-(4-benzylpiperidinyl)-1-naphthoxy-2-propanol as a selective dopamine D4 receptor Ligand. A systematic structure-activity study revealed that the benzyl group could be replaced with phenoxy and the naphthalene with phenyl to improve potency almost tenfold. The (R) enantiomer of this compound had a D4 affinity of 2 nM and was over 100-fold weaker at dopamine D2 and D3 receptors. (C) 1997 Elsevier Science Ltd.