ethyl 4-(dimethylamino)-3-methoxybenzoate | 205187-82-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 4-(dimethylamino)-3-methoxybenzoate
• CAS: 205187-82-2
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: SNHJJAIUTSABTM-UHFFFAOYSA-N

物化性质

• 沸点：
  311.1±27.0 °C(Predicted)
• 密度：
  1.084±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-(dimethylamino)-3-methoxybenzoate 在 二异丁基氢化铝 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 0.5h， 以90%的产率得到4-dimethylamino-3-methoxy-benzyl alcohol
  参考文献：
  名称：

  Antibody-Catalyzed Decarboxylative Oxidation of Vanillylmandelic Acid

  摘要：

  The most important industrial process for the synthesis of vanillin is performed in two steps involving an electrophilic aromatic substitution of glyoxylic acid on guaiacol followed by an oxidative decarboxylation of the intermediary alpha-hydroxy acids formed, thereby producing not only vanillin, but also byproducts which have to be eliminated. In the present study, we took advantage of the high specificity of catalytic antibodies to improve the synthesis of vanillin. Among ii monoclonal antibodies elicited against the quaternary ammonium hapten H3, antibody H3-12 was found to catalyze the oxidative decarboxylation of vanillylmandelic acid (VMA), the precursor of vanillin, in the presence of sodium metaperiodate. The kinetic data of the antibody-catalyzed reaction are consistent with an ordered binding mechanism. At pH 9.0, H3-12 catalyzed the transformation of VMA into vanillin with a k(cat) of 2.70 min(-1), a Michaelis-Menten constant K-a for the binary complex of 260 mu M, and a K-b for the ternary complex of 2100 mu M. The catalyzed reaction was fully inhibited by a hapten analogue with a K-i, of 10 mu M. The fine specificity of anti-H3 monoclonal antibodies was determined using H3-related compounds with a competitive enzyme immunoassay. Controls demonstrating that catalytic activity is actually related to antibody binding, and mechanistic studies, are also presented.

  DOI：

  10.1021/ja9724811
• 作为产物：
  描述：

  聚合甲醛 、 3-甲氧基-4-氨基苯甲酸甲酯 在 sodium tetrahydroborate 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以88%的产率得到ethyl 4-(dimethylamino)-3-methoxybenzoate
  参考文献：
  名称：

  Antibody-Catalyzed Decarboxylative Oxidation of Vanillylmandelic Acid

  摘要：

  The most important industrial process for the synthesis of vanillin is performed in two steps involving an electrophilic aromatic substitution of glyoxylic acid on guaiacol followed by an oxidative decarboxylation of the intermediary alpha-hydroxy acids formed, thereby producing not only vanillin, but also byproducts which have to be eliminated. In the present study, we took advantage of the high specificity of catalytic antibodies to improve the synthesis of vanillin. Among ii monoclonal antibodies elicited against the quaternary ammonium hapten H3, antibody H3-12 was found to catalyze the oxidative decarboxylation of vanillylmandelic acid (VMA), the precursor of vanillin, in the presence of sodium metaperiodate. The kinetic data of the antibody-catalyzed reaction are consistent with an ordered binding mechanism. At pH 9.0, H3-12 catalyzed the transformation of VMA into vanillin with a k(cat) of 2.70 min(-1), a Michaelis-Menten constant K-a for the binary complex of 260 mu M, and a K-b for the ternary complex of 2100 mu M. The catalyzed reaction was fully inhibited by a hapten analogue with a K-i, of 10 mu M. The fine specificity of anti-H3 monoclonal antibodies was determined using H3-related compounds with a competitive enzyme immunoassay. Controls demonstrating that catalytic activity is actually related to antibody binding, and mechanistic studies, are also presented.

  DOI：

  10.1021/ja9724811