(E)-1-(3-Allyl-2-hydroxy-phenyl)-3-phenyl-propenone | 178666-52-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-(3-Allyl-2-hydroxy-phenyl)-3-phenyl-propenone
• 英文别名: 1-(2-hydroxy-3-prop-2-enylphenyl)-3-phenylprop-2-en-1-one
• CAS: 178666-52-9
• 化学式: C₁₈H₁₆O₂
• 分子量: 264.324
• InChiKey: HVUIFKLYEHROGV-UHFFFAOYSA-N

物化性质

• 沸点：
  437.1±45.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-1-(3-Allyl-2-hydroxy-phenyl)-3-phenyl-propenone 在 sodium hydroxide 、 双氧水 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 3-Methoxy-2-phenyl-8-prop-2-enylchromen-4-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 3-Alkoxy Analogues of Flavone-8-acetic Acid

  摘要：

  New analogues of flavone-8-acetic acid were synthesized, bearing an alkoxy group in position 3 and different substituents on the benzene ring in position 2 of the flavone nucleus. The compounds were tested for direct cytotoxicity against four human tumor cell lines and for indirect antitumor effects by measuring their ability to enhance lytic properties of murine macrophages and human monocytes. Though direct toxicity was very low, the compounds were able to induce significant indirect toxicity. Notably, most of them (4c, 4d, 4e, 4f, 4h, 4i, 4m, 4n, and 4o) showed important activity on human monocytes and could be regarded as the first flavone derivatives endowed with such activity. Particularly interesting seem to be compounds 4m and 4n, which showed IC50 values up to 7 times higher than DMXAA, which has now completed phase I clinical trials.

  DOI：

  10.1021/jm030771o
• 作为产物：
  描述：

  1-(2-(烯丙氧基)苯基)乙酮 在 sodium acetate 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 180.0 ℃ 、3.0 MPa 条件下， 反应 1.0h， 生成 (E)-1-(3-Allyl-2-hydroxy-phenyl)-3-phenyl-propenone
  参考文献：
  名称：

  8-Prenylflavanones通过微波促进的串联Claisen重排/ 6-endo-trig环化和交叉易位

  摘要：

  微波照射邻烯丙氧基查耳酮可促进克莱森重排和6-内-trig环化的串联序列。烯烃交叉复分解然后提供异戊烯基黄酮。该方法除其他外，已用于合成角铬烯化的天然产物及其线性异构体。两者都分别发生在印度和尼日利亚本土的药用植物中。

  DOI：

  10.1002/ejoc.202001378

文献信息

• 8‐Prenylflavanones through Microwave Promoted Tandem Claisen Rearrangement/6‐<i>endo</i>‐trig Cyclization and Cross Metathesis
  作者：Christiane Schultze、Stefan Foß、Bernd Schmidt

  DOI：10.1002/ejoc.202001378

  日期：2020.12.20

  Microwave irradiation of ortho‐allyloxy chalcones promotes a tandem sequence of Claisen rearrangement and 6‐endo‐trig‐cyclization. Olefin cross metathesis then furnishes prenylated flavonoids. The method has, inter alia, been applied to the synthesis of an angular chromene‐annellated natural product and its linear isomer. Both occur in medicinal plants indigenous in India and Nigeria respectively.

  微波照射邻烯丙氧基查耳酮可促进克莱森重排和6-内-trig环化的串联序列。烯烃交叉复分解然后提供异戊烯基黄酮。该方法除其他外，已用于合成角铬烯化的天然产物及其线性异构体。两者都分别发生在印度和尼日利亚本土的药用植物中。
• Synthesis and Biological Evaluation of 3-Alkoxy Analogues of Flavone-8-acetic Acid
  作者：Silvia Gobbi、Angela Rampa、Alessandra Bisi、Federica Belluti、Lorna Piazzi、Piero Valenti、Anna Caputo、Antonella Zampiron、Maria Carrara

  DOI：10.1021/jm030771o

  日期：2003.8.1

  New analogues of flavone-8-acetic acid were synthesized, bearing an alkoxy group in position 3 and different substituents on the benzene ring in position 2 of the flavone nucleus. The compounds were tested for direct cytotoxicity against four human tumor cell lines and for indirect antitumor effects by measuring their ability to enhance lytic properties of murine macrophages and human monocytes. Though direct toxicity was very low, the compounds were able to induce significant indirect toxicity. Notably, most of them (4c, 4d, 4e, 4f, 4h, 4i, 4m, 4n, and 4o) showed important activity on human monocytes and could be regarded as the first flavone derivatives endowed with such activity. Particularly interesting seem to be compounds 4m and 4n, which showed IC50 values up to 7 times higher than DMXAA, which has now completed phase I clinical trials.