diphenyl [1-(p-methoxybenzoyl)-3,4-didehydro-2-piperidyl]malonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: diphenyl [1-(p-methoxybenzoyl)-3,4-didehydro-2-piperidyl]malonate
• 英文别名: diphenyl 2-[(6R)-1-(4-methoxybenzoyl)-3,6-dihydro-2H-pyridin-6-yl]propanedioate
• 化学式: C₂₈H₂₅NO₆
• 分子量: 471.51
• InChiKey: XURQBPGDLCHHEG-XMMPIXPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  丙二酸二苯酯 、 1-(p-methoxybenzoyl)-3,4-didehydro-2-methoxypiperidine 在 copper(II) bis(trifluoromethanesulfonate) 、 (S,S)-2,2'-异亚丙基双(4-苯基-2-恶唑啉) 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 diphenyl [1-(p-methoxybenzoyl)-3,4-didehydro-2-piperidyl]malonate 、
  参考文献：
  名称：

  Highly enantioselective introduction of bis(alkoxycarbonyl)methyl group into the 2-position of piperidine skeleton

  摘要：

  Copper ion catalyzed carbon-carbon bond forming reaction of N-acyliminium ions with diaryl the method were 2-methoxy-3,4-didehydropiperidines, which were easily prepared through electrochemical oxidation of 1-(p-methoxybenzoyl)piperidine in methanol followed by the conversion of the oxidation product to didehydropiperidine derivative, which was subjected to a chiral Cu(II) catalyzed coupling reaction with diaryl malonates affording diaryl 2-piperidylmalonates. The maximum % ee (ee, enantiomeric excess) was 97% when di-p-chlorophenyl malonate was used as a nucleophile. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.04.039