(2Z)-2-(3,4-dimethoxybenzylidene)-5-[(dimethylamino)-methyl]-6-hydroxy-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)-2-(3,4-dimethoxybenzylidene)-5-[(dimethylamino)-methyl]-6-hydroxy-7-methyl-1-benzofuran-3(2H)-one
• 英文别名: (Z)-2-(3,4-dimethoxybenzylidene)-5-((dimethylamino)methyl)-6-hydroxy-7-methylbenzofuran-3(2H)-one；(2Z)-2-[(3,4-dimethoxyphenyl)methylidene]-5-[(dimethylamino)methyl]-6-hydroxy-7-methyl-1-benzofuran-3-one
• 化学式: C₂₁H₂₃NO₅
• 分子量: 369.417
• InChiKey: MSVQUPFCCLDDCC-NVMNQCDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2Z)-2-(3,4-dimethoxybenzylidene)-5-[(dimethylamino)-methyl]-6-hydroxy-7-methyl-1-benzofuran-3(2H)-one 、 新烟碱 以 1,4-二氧六环 为溶剂， 以87%的产率得到(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：

  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 、 异丙醇 为溶剂， 生成 (2Z)-2-(3,4-dimethoxybenzylidene)-5-[(dimethylamino)-methyl]-6-hydroxy-7-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

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。
• 6-Hydroxyaurone aminomethyl derivatives in the inverse electron-demand Diels–Alder reaction
  作者：Antonina V. Popova、Galyna P. Mrug、Svitlana P. Bondarenko、Mikhaylo S. Frasinyuk

  DOI：10.1007/s10593-019-02598-z

  日期：2019.12

  2-benzylidene derivatives of difuro[2,3-b:2',3'-f]chromen-3(2H)-one, furo[2,3-f]pyrano[2,3-b]chromen-3(2H)-one, difuro[2,3-b:3',2'-g]chromen-3(2H)-one, and furo[3,2-g]pyrano[2,3-b]chromen-3(2H)-one heterocyclic systems were synthesized. A similar reaction with cyclic enamines, accompanied by subsequent transformation of hemi-aminals, led to the formation of partially hydrogenated derivatives of furo[2

  研究了逆电子需求异Diels-Alder反应中7-二甲基氨基甲基-6-羟基金酮和5-二甲基氨基甲基-6-羟基-7-甲基酮的转化。由于含有苯并呋喃酮部分的邻醌甲基化物的原位热形成和环状乙烯基酯的环加成反应，双呋喃[2,3- b：2'，3'- f ] chromen-3（2）的2-亚苄基衍生物H）-一，呋喃[2,3- f ]吡喃并[2,3- b ] chromen -3（2 H）-一，呋喃[2,3- b：3'，2'- g ] chromen-3 （2 H）-一和呋喃[3,2- g ]吡喃[2,3- b合成了] chromen-3（2 H）-杂环系统。与环状烯胺的类似反应，伴随着半缩醛的后续转化，导致呋喃[2,3- a ]黄原胶-3（2 H）-one和呋喃[3,2- b ]的部分氢化衍生物的形成] xanthen-3（2 H）-1 。
• 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.