(2Z)-6-hydroxy-2-(3,4-dimethoxybenzylidene)-7-methyl-1-benzofuran-3(2H)-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: (2Z)-6-hydroxy-2-(3,4-dimethoxybenzylidene)-7-methyl-1-benzofuran-3(2H)-one
• 英文别名: (Z)-2-(3,4-dimethoxybenzylidene)-6-hydroxy-7-methylbenzofuran-3(2H)-one；(2Z)-2-[(3,4-dimethoxyphenyl)methylidene]-6-hydroxy-7-methyl-1-benzofuran-3-one
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: HOULNYCCAXFRNL-SXGWCWSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2Z)-6-hydroxy-2-(3,4-dimethoxybenzylidene)-7-methyl-1-benzofuran-3(2H)-one 以 1,4-二氧六环 、 异丙醇 为溶剂， 生成 (2Z)-2-(3,4-dimethoxybenzylidene)-6-hydroxy-7-methyl-5-{[(2S)-2-(pyridin-3-yl)piperidin-1-yl]methyl}-1-benzofuran-3(2H)-one
  参考文献：
  名称：

  Synthesis of anabasine-containing aminomethyl derivatives of 6-hydroxyaurones

  摘要：

  uAminomethylation of aurones was studied by using anabasine. The reaction in the case of 6-hydroxyaurones was shown to selectively provide 7-aminomethyl-6-hydroxyaurones, while 5-aminomethyl-6-hydroxy-7-methylaurones could be obtained by transamination of 5-dimethylaminomethyl derivatives of 6-hydroxy-7-methylaurones in the presence of anabasine.

  DOI：

  10.1007/s10593-019-02444-2
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 、 6-羟基-7-甲基苯并呋喃-3-酮 在 potassium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 以83%的产率得到(2Z)-6-hydroxy-2-(3,4-dimethoxybenzylidene)-7-methyl-1-benzofuran-3(2H)-one
  参考文献：
  名称：

  Synthesis of Flavonoid Derivatives of Cytisine. 5. Aminomethylation of 6-Hydroxyaurones

  摘要：

  研究了生物碱金雀花碱对6-羟基和6-羟基-7-甲基香豆酮进行氨基甲基化的反应。结果表明，6-羟基香豆酮的氨基甲基化发生在苯并呋喃环的7位上，如果7位已被占据，则发生在5位上。

  DOI：

  10.1007/s10600-017-2096-y

文献信息

• Observations from aminomethylation of 7-substituted 6-hydroxyaurones
  作者：Svitlana P. Bondarenko、Mykhaylo S. Frasinyuk

  DOI：10.1007/s10593-018-2347-2

  日期：2018.8

  Aminomethylation of 7-substituted 6-hydroxyaurones was studied using primary and secondary amines. In the case of 6-hydroxy-7-methylaurones, their 5-dialkylaminomethyl derivatives or 7-benzylidene-3,4-dihydro-2Н-furo[3,2-g][1,3]benzoxazin-6(7Н)-ones were formed. The aminomethylation reaction of 6,7-dihydroxyaurones produced only 5-aminomethyl derivatives.

  使用伯胺和仲胺研究了7-取代的6-羟基金酮的氨基甲基化。在6-羟基-7- methylaurones，它们的5二烷基氨基甲基衍生物或7-苄基-3,4-二氢-2H-2的情况下Н -呋喃并[3,2-克] [1,3]苯并恶嗪-6-（7 Н）-形成了。6，7-二羟基金酮的氨基甲基化反应仅产生5-氨基甲基衍生物。
• Synthesis of Flavonoid Derivatives of Cytisine. 5. Aminomethylation of 6-Hydroxyaurones
  作者：A. V. Popova、S. P. Bondarenko、E. V. Podobii、M. S. Frasinyuk、V. I. Vinogradova

  DOI：10.1007/s10600-017-2096-y

  日期：2017.7

  Aminomethylation of 6-hydroxy- and 6-hydroxy-7-methylaurones by the alkaloid cytisine was studied. It was shown that the aminomethylation of the 6-hydroxyaurones occurred at the 7-position of the benzofuran ring and at the 5-position if the 7-position was occupied.

  研究了生物碱金雀花碱对6-羟基和6-羟基-7-甲基香豆酮进行氨基甲基化的反应。结果表明，6-羟基香豆酮的氨基甲基化发生在苯并呋喃环的7位上，如果7位已被占据，则发生在5位上。
• Synthesis of anabasine-containing aminomethyl derivatives of 6-hydroxyaurones
  作者：Antonina V. Popova、Svitlana P. Bondarenko、Valentina I. Vinogradova、Mykhaylo S. Frasinyuk

  DOI：10.1007/s10593-019-02444-2

  日期：2019.3

  uAminomethylation of aurones was studied by using anabasine. The reaction in the case of 6-hydroxyaurones was shown to selectively provide 7-aminomethyl-6-hydroxyaurones, while 5-aminomethyl-6-hydroxy-7-methylaurones could be obtained by transamination of 5-dimethylaminomethyl derivatives of 6-hydroxy-7-methylaurones in the presence of anabasine.