4a,7-bis-(2-acetamidoethyl)-4-<2-(2-acetamidoethyl)-4,5-diacetyloxyphenyl>-3-acetyloxy-10-(2-carboethyl)-2,4a-dihydro-10H-phenoxazin-2-one | 146004-55-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 4a,7-bis-(2-acetamidoethyl)-4-<2-(2-acetamidoethyl)-4,5-diacetyloxyphenyl>-3-acetyloxy-10-(2-carboethyl)-2,4a-dihydro-10H-phenoxazin-2-one
• CAS: 146004-55-9
• 化学式: C₃₉H₄₄N₄O₁₃
• 分子量: 776.797
• InChiKey: FPKVRRRRASFNHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  56.0
• 可旋转键数：
  16.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  233.04
• 氢给体数：
  4.0
• 氢受体数：
  13.0

反应信息

• 作为产物：
  描述：

  乙酸酐 、 4a,7-bis-(2-acetamidoethyl)-4-<2-(2-acetamidoethyl)-4,5-dihydroxyphenyl>-10-(2-carboethyl)-3-hydroxy-2,4a-dihydro-10H-phenoxazin-2-one 在 吡啶 作用下， 以8.6 mg的产率得到4a,7-bis-(2-acetamidoethyl)-4-<2-(2-acetamidoethyl)-4,5-diacetyloxyphenyl>-3-acetyloxy-10-(2-carboethyl)-2,4a-dihydro-10H-phenoxazin-2-one
  参考文献：
  名称：

  Catecholamine-protein conjugates: isolation of 4-phenylphenoxazin-2-ones from oxidative coupling of N-acetyldopamine with aliphatic amino acids

  摘要：

  4-Phenylphenoxazinones 4 were isolated after biomimetic oxidation, using diphenoloxidases of insect cuticle, mushroom tyrosinase, or after autoxidation of N-acetyldopamine (1) in the presence of beta-alanine, beta-alanine methyl ester or N-acetyl-L-lysine. They are formed presumably by addition of 2-aminoalkyl-5-alkylphenols 2 to the o-quinone of biphenyltetrol 3 which, in turn, arises from oxidative coupling of 1. The structures of 4 present the first examples for the assembly of reasonably stable intermediates in the rather complex process of chemical modifications of aliphatic amino acid residues by o-quinones.

  DOI：

  10.1016/s0040-4020(01)81991-8