3-methoxy-3'-methylchalcone

• 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: 3-methoxy-3'-methylchalcone
• 英文别名: (E)-3-(3-methoxyphenyl)-1-m-tolylprop-2-en-1-one；(2E)-3-(3-Methoxyphenyl)-1-(3-methylphenyl)prop-2-en-1-one；(E)-3-(3-methoxyphenyl)-1-(3-methylphenyl)prop-2-en-1-one
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: OXDAJWCEORAZDQ-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-甲氧基肉桂酸 、 3-methylphenyloxoacetic acid 在 sodium persulfate 、 potassium carbonate 、 silver nitrate 作用下， 以 水 为溶剂， 反应 24.0h， 以78%的产率得到3-methoxy-3'-methylchalcone
  参考文献：
  名称：

  Silver-Catalyzed Double-Decarboxylative Cross-Coupling of α-Keto Acids with Cinnamic Acids in Water: A Strategy for the Preparation of Chalcones

  摘要：

  A silver-catalyzed double-decarboxylative protocol has been proposed for the construction of chalcone derivatives via cascade coupling of substituted alpha-keto acids with cinnamic acids under the mild aqueous conditions. The developed method for constructing C-C bonds via double-decarboxylative reactions is efficient, practical, and environmentally benign by using the readily available starting materials. It should provide a promising synthesis candidate for the formation of diverse and useful chalcone derivatives in the fields of synthetic and pharmaceutical chemistry.

  DOI：

  10.1021/jo502642n

文献信息

• Antitumorigenic Activities of Chalcones. I. Inhibitory Effects of Chalcone Derivatives on 32Pi-Incorporation into Phospholipids of HeLa Cells Promoted by 12-O-Tetradecanoyl-phorbol 13-Acetate(TPA).
  作者：Susumu IWATA、Takeshi NISHINO、Nobuyuki NAGATA、Yoshiko SATOMI、Hoyoku NISHINO、Shoji SHIBATA

  DOI：10.1248/bpb.18.1710

  日期：——

  More than forty chalcone derivatives were synthesized to examine their structure-activity relationship against tumorigenesis. As a primary screening test, the inhibitory activities of the chalcones for the 32Pi-incorporation into phospholipids of HeLa cells enhanced by 12-O-tetradecanoyl-phorbol 13-acetate (TPA) were examined. 3-Hydroxy-chalcone derivatives possessing methyl group in 3'-, 4'-, or 2'-position and isoliquiritigenin homologs showed potent inhibitory activities in the phosphorylation test, which suggests their antitumorigenic effects.

  合成了四十余种查耳酮衍生物，以研究其结构与抗肿瘤发生活性之间的关系。作为初步筛选测试，检测了查耳酮对12-O-十四烷酰佛波醇-13-乙酸酯（TPA）增强的HeLa细胞磷脂中32Pi掺入的抑制活性。在3'-、4'-或2'-位具有甲基的3-羟基查耳酮衍生物和异甘草素同系物在磷酸化试验中显示出强大的抑制活性，这表明它们具有抗肿瘤发生作用。
• Silver-Catalyzed Double-Decarboxylative Cross-Coupling of α-Keto Acids with Cinnamic Acids in Water: A Strategy for the Preparation of Chalcones
  作者：Ning Zhang、Daoshan Yang、Wei Wei、Li Yuan、Fafa Nie、Laijin Tian、Hua Wang

  DOI：10.1021/jo502642n

  日期：2015.3.20

  A silver-catalyzed double-decarboxylative protocol has been proposed for the construction of chalcone derivatives via cascade coupling of substituted alpha-keto acids with cinnamic acids under the mild aqueous conditions. The developed method for constructing C-C bonds via double-decarboxylative reactions is efficient, practical, and environmentally benign by using the readily available starting materials. It should provide a promising synthesis candidate for the formation of diverse and useful chalcone derivatives in the fields of synthetic and pharmaceutical chemistry.