3-[6-(4-acetophenyl)amino-3,4-dihydroxyphenyl]propanoic acid | 1663506-80-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[6-(4-acetophenyl)amino-3,4-dihydroxyphenyl]propanoic acid
• CAS: 1663506-80-6
• 化学式: C₁₇H₁₇NO₅
• 分子量: 315.326
• InChiKey: ILZNLLRQWAINLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  106.86
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  3,4-二羟基苯基丙酸 、 4-氨基苯乙酮 在 Xylaria polymorpha laccase 、 ABTS 作用下， 以 aq. acetate buffer 为溶剂， 反应 3.75h， 以86%的产率得到3-[6-(4-acetophenyl)amino-3,4-dihydroxyphenyl]propanoic acid
  参考文献：
  名称：

  Selective oxidation and N-coupling by purified laccase of Xylaria polymorpha MTCC-1100

  摘要：

  The chemical route of oxidation of methyl group to its aldehyde is inconvenient because once a methyl group is attacked, it is likely to be oxidized to the carboxylic acid and it is very difficult to stop the reaction at the aldehyde stage. Fungal laccases can be used for such oxidation reaction and the reaction can be completed sharply within 1-2 hrs. Coupling of amines are another important reactions known forfungal laccases; coupling reactions generally take 3-7 hrs. We have used the purified laccase of molecular weight 63 kDa obtained from the fungal strainXylaria polymorpha MTCC-100 with activity of 1.95 IU/mL for selective oxidation of 2-fluorotoluene, 4-fluorotoluene, and 2-chlorotoluene to 2-fluorobenzaldehyde, 4-fluorobenzaldehyde, and 2-chlorobenzaldehyde, respectively, and syntheses of 3-(3,4-dihydroxyphenyl)-propionic acid derivatives by N-coupling of amines. In each oxidation reactions, ABTS was used as mediator molecule. All the syntheses are ecofriendly and were performed at room temperature.

  DOI：

  10.1134/s1068162014040025

文献信息

• Synthetic applications of purified laccase from Pleurotus sajor caju MTCC-141
  作者：Pankaj Kumar Chaurasia、Shashi Lata Bharati、Sunil Kumar Singh、Sudha Yadava

  DOI：10.1134/s1070363215010302

  日期：2015.1

  The study is devoted to the role of laccase, purified from the liquid culture medium of the indigenous fungal strain Pleurotus sajor caju MTCC-141, in selective bioconversion of toluene derivatives into substituted benzaldehydes with high yield. Coupling reactions of 3-(3,4-dihydroxyphenyl)propionic acid with 4-aminobenzoic, 4-aminoacetophenone and 1-hexylamine proceeded at room temperature under the action of laccase to give the corresponding products with excellent yields.