4-oxo-beta-Dioxadrol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-oxo-beta-Dioxadrol
• 英文别名: (2S)-2-[(4R)-2,2-diphenyl-1,3-dioxolan-4-yl]piperidin-4-one
• 化学式: C₂₀H₂₁NO₃
• 分子量: 323.392
• InChiKey: CDXSSMFKKLDFOV-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (+/-)-trans-1-benzyl-2-(2,2-diphenyl-1,3-dioxolan-4-yl)piperidin-4-one 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以86%的产率得到4-oxo-beta-Dioxadrol
  参考文献：
  名称：

  Synthesis and NMDA-receptor affinity of 4-oxo-dexoxadrol derivatives

  摘要：

  A synthesis of novel dexoxadrol analogues is described, which allows modifications of the piperidine substructure. The key step of the synthesis is a hetero Diels-Alder reaction of the imine 12 with Danishefsky's diene 6. After separation of the diastereomeric piperidones 14a and 14b, the relative configuration of the unlike configured piperidone 15b was determined by X-ray crystal structure analysis. In receptor binding studies the like configured secondary amine 15a (racemate) showed considerable affinity toward the phencyclidine binding site of the NMDA receptor (K-i = 470 nM). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.020