4a,8-bis-(2-acetamidoethyl)-4-<2-(2-acetamidoethyl)-4,5-dihydroxyphenyl>-10-(2-carboethyl)-3-hydroxy-2,4a-dihydro-10H-phenoxazin-2-one | 146004-49-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 4a,8-bis-(2-acetamidoethyl)-4-<2-(2-acetamidoethyl)-4,5-dihydroxyphenyl>-10-(2-carboethyl)-3-hydroxy-2,4a-dihydro-10H-phenoxazin-2-one
• 英文别名: 3-[4a,8-Bis(2-acetamidoethyl)-4-[2-(2-acetamidoethyl)-4,5-dihydroxyphenyl]-3-hydroxy-2-oxophenoxazin-10-yl]propanoic acid
• CAS: 146004-49-1
• 化学式: C₃₃H₃₈N₄O₁₀
• 分子量: 650.686
• InChiKey: AXWGVQPDYSMCAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  215
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  N-[2-(3,4-二羟基苯基)乙基]乙酰胺 、 β-丙氨酸 反应 6.0h， 以0.3%的产率得到4a,8-bis-(2-acetamidoethyl)-4-<2-(2-acetamidoethyl)-4,5-dihydroxyphenyl>-10-(2-carboethyl)-3-hydroxy-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

文献信息

• Catecholamine-protein conjugates: isolation of 4-phenylphenoxazin-2-ones from oxidative coupling of N-acetyldopamine with aliphatic amino acids
  作者：Martin G. Peter、Svend Olav Andersen、Rudolf Hartmann、Merle Miessner、Peter Roepstorff

  DOI：10.1016/s0040-4020(01)81991-8

  日期：——

  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.