O=C(/C=C/c1ccccc1)N2/C=C\CCC2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: O=C(/C=C/c1ccccc1)N2/C=C\CCC2
• 英文别名: 1-(3,4-dihydro-2H-pyridin-1-yl)-3-phenylprop-2-en-1-one
• 化学式: C₁₄H₁₅NO
• 分子量: 213.279
• InChiKey: HLJGMKMZIKDPPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  Tripiperidin 、 肉桂酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以39%的产率得到O=C(/C=C/c1ccccc1)N2/C=C\CCC2
  参考文献：
  名称：

  Cytotoxic Amides from Fruits of Kawakawa, Macropiper excelsum

  摘要：

  Cytotoxic amides have been isolated from the fruits of the endemic New Zealand medicinal plant kawakawa, Macropiper excelsum (Piperaceae). The main amide was piperchabamide A and this is the first report of this rare compound outside the genus Piper. Eleven other amides were purified including two new compounds with the unusual 3,4-dihydro-1(2H)-pyridinyl group. The new compounds were fully characterized by 2DNMR spectroscopy, which showed a slow exchange between two rotamers about the amide bond, and they were chemically synthesized. In view of the antitumor activity of the related piperlongumine, all of these amides plus four synthetic analogs were tested for cytotoxicity. The most active was the piperine homolog piperdardine, with an IC50 of 14 mu M against HT 29 colon cancer cells.

  DOI：

  10.1055/s-0035-1546106