3,4-二羟基吲哚-2-羧酸苄基酯 | 113934-61-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 3,4-二羟基吲哚-2-羧酸苄基酯
• 英文名称: 3,4-dihydroxyindole-2-carboxylic acid benzyl ester
• 英文别名: benzyl 5,6-dihydroxyindole-2-carboxylate；Benzyl 5,6-dihydroxy-1H-indole-2-carboxylate
• CAS: 113934-61-5
• 化学式: C₁₆H₁₃NO₄
• 分子量: 283.284
• InChiKey: YPNVJYKOQBLSMP-UHFFFAOYSA-N

物化性质

• 沸点：
  547.7±45.0 °C(Predicted)
• 密度：
  1.435±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  82.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-二羟基吲哚-2-羧酸苄基酯 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 6.0h， 以84%的产率得到5,6-二羟基-2-吲哚甲酸
  参考文献：
  名称：

  Chioccara, Francesco; Novellino, Ettore, Synthetic Communications, 1987, vol. 17, # 15, p. 1815 - 1822

  摘要：

  DOI：
• 作为产物：
  描述：

  benzyl 6-hydroxy-5-oxo-3,5-dihydro-2H-indole-2-carboxylate 在 sodium acetate buffer 、 zinc diacetate 作用下， 反应 0.08h， 生成 3,4-二羟基吲哚-2-羧酸苄基酯
  参考文献：
  名称：

  Chioccara, Francesco; Novellino, Ettore, Synthetic Communications, 1987, vol. 17, # 15, p. 1815 - 1822

  摘要：

  DOI：

文献信息

• Synthesis and Polymerization Studies of Organic-Soluble Eumelanins
  作者：Kirsten J. Lawrie、Paul Meredith、Ross P. McGeary

  DOI：10.1111/j.1751-1097.2007.00295.x

  日期：2008.5

  AbstractThe isolation, structure determination and chemical characterization of eumelanins has been plagued by their very low solubility in organic solvents. To gain insights into the structure and reactivity of these unusual and important biologic macromolecules and to pave the way for their use in electronics, we have prepared soluble melanins via the synthesis of monomeric precursors containing lipophilic substituents. Two such monomers derived from 5,6‐dihydroxyindole‐2‐carboxylic acid (DHICA) were prepared, namely the benzyl and octyl ester derivatives. Both benzyl and octyl ester monomers were oxidatively polymerized to yield dark, melanin‐like pigments. These polymerization processes were followed by UV–visible, fluorescence and NMR spectroscopy. These studies showed that the polymerizations proceeded by cross‐linking at the 4‐ and 7‐positions of the indole nucleus and led to highly heterogeneous polymeric products. Incorporation of a lipophilic benzyl or octyl group resulted in enhanced solubility of the pigments in a wide range of organic solvents. The UV–visible spectra of the organically soluble synthetic melanins were essentially identical to that of natural eumelanin.
• CHIOCCARA, FRANCESCO;NOVELLINO, ETTORE, SYNTH. COMMUN., 17,(1987) N 5, 1815-1821
  作者：CHIOCCARA, FRANCESCO、NOVELLINO, ETTORE

  DOI：——

  日期：——