1-(p-methoxybenzoyl)-3,4-didehydro-2-methoxypiperidine

• 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: 1-(p-methoxybenzoyl)-3,4-didehydro-2-methoxypiperidine
• 英文别名: (6-methoxy-3,6-dihydro-2H-pyridin-1-yl)-(4-methoxyphenyl)methanone
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: DYLLNMZSKWWAMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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， 以78%的产率得到dimethyl 2-[1-(4-methoxybenzoyl)-3,6-dihydro-2H-pyridin-6-yl]propanedioate
  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

文献信息

• Copper ion-catalyzed asymmetric carbon–carbon bond-forming reaction at the 2-position of a piperidine skeleton
  作者：Osamu Onomura、Yasuhisa Kanda、Yasuharu Nakamura、Toshihide Maki、Yoshihiro Matsumura

  DOI：10.1016/s0040-4039(02)00449-5

  日期：2002.4

  An asymmetric carbon carbon bond-forming reaction at the 2-position of a piperidine skeleton was exploited. This method consisted of a reaction between 1-benzoyl-3,4-didehydro-2-methoxypiperidines and dimethyl malonate catalyzed by Cu(II)-chiral 2,2'-isopropylidenebis(4-phenyl-2-oxazoline) to afford a 2-substituted piperidine skeleton with moderate enantioselectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Highly enantioselective introduction of bis(alkoxycarbonyl)methyl group into the 2-position of piperidine skeleton
  作者：Yoshihiro Matsumura、Diashirou Minato、Osamu Onomura

  DOI：10.1016/j.jorganchem.2006.04.039

  日期：2007.1

  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.