7-amino-8-(2-aminoethyl)-3-hydroxy-2-oxo-2,3,4,10-tetrahydro<3,4-a>iminoethanophenoxazine | 145069-19-8

• 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: 7-amino-8-(2-aminoethyl)-3-hydroxy-2-oxo-2,3,4,10-tetrahydro<3,4-a>iminoethanophenoxazine
• 英文别名: 5-Amino-6-(2-aminoethyl)-13-hydroxy-2-oxa-9,14-diazatetracyclo[11.3.1.01,10.03,8]heptadeca-3(8),4,6,10-tetraen-12-one
• CAS: 145069-19-8
• 化学式: C₁₆H₂₀N₄O₃
• 分子量: 316.36
• InChiKey: BAPRZXIWWNTJMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  123
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 7-amino-8-(2-aminoethyl)-3-hydroxy-2-oxo-2,3,4,10-tetrahydro<3,4-a>iminoethanophenoxazine 在 吡啶 作用下， 以33%的产率得到Acetic acid 7-acetylamino-4a,8-bis-(2-acetylamino-ethyl)-2-oxo-2,10-dihydro-4aH-phenoxazin-3-yl ester
  参考文献：
  名称：

  A new oxidation pathway of the neurotoxin 6-aminodopamine. Isolation and characterisation of a dimer with a tetrahydro[3,4a]iminoethanophenoxazine ring system.

  摘要：

  Oxidation of the neurotoxin 6-aminodopamine (1) is known to proceed through the o-quinone 3, which undergoes intramolecular cyclisation to give 5,6-dihydroxyindole (6). In a re-examination of the reaction, we have found that at concentrations of 1 higher than 5 x 10(-3) M a quite different course prevails, leading to the formation of the novel 7-amino-8-(2-aminoethyl)-3-hydroxy-2-oxo-2,3,4,10-tetrahydro [3,4a] iminoethanophenoxazine (7). Product 7 was formed by aerobic, chemical (persulphate, periodate) or enzymatic (tyrosinase, peroxidase/H2O2) oxidation of 1. on acetylation, 7 afforded the tetraacetate 8. Oxidation of the model compound 5-amino-4-methylcatechol (9) proceeded similarly as that of 1, to give the tetrahydrophenoxazinedione 11.

  DOI：

  10.1016/s0040-4020(01)86599-6
• 作为产物：
  描述：

  7-chloro-5,10-dihydro-4H-thieno[3,2-c][1]benzazepin-4-one 在 ammonium persulfate 作用下， 以 水 为溶剂， 反应 1.5h， 以38%的产率得到7-amino-8-(2-aminoethyl)-3-hydroxy-2-oxo-2,3,4,10-tetrahydro<3,4-a>iminoethanophenoxazine
  参考文献：
  名称：

  A new oxidation pathway of the neurotoxin 6-aminodopamine. Isolation and characterisation of a dimer with a tetrahydro[3,4a]iminoethanophenoxazine ring system.

  摘要：

  Oxidation of the neurotoxin 6-aminodopamine (1) is known to proceed through the o-quinone 3, which undergoes intramolecular cyclisation to give 5,6-dihydroxyindole (6). In a re-examination of the reaction, we have found that at concentrations of 1 higher than 5 x 10(-3) M a quite different course prevails, leading to the formation of the novel 7-amino-8-(2-aminoethyl)-3-hydroxy-2-oxo-2,3,4,10-tetrahydro [3,4a] iminoethanophenoxazine (7). Product 7 was formed by aerobic, chemical (persulphate, periodate) or enzymatic (tyrosinase, peroxidase/H2O2) oxidation of 1. on acetylation, 7 afforded the tetraacetate 8. Oxidation of the model compound 5-amino-4-methylcatechol (9) proceeded similarly as that of 1, to give the tetrahydrophenoxazinedione 11.

  DOI：

  10.1016/s0040-4020(01)86599-6

文献信息

• A new oxidation pathway of the neurotoxin 6-aminodopamine. Isolation and characterisation of a dimer with a tetrahydro[3,4a]iminoethanophenoxazine ring system.
  作者：Alessandra Napolitano、Marco d'Ischia、Claudio Costantini、Giuseppe Prota

  DOI：10.1016/s0040-4020(01)86599-6

  日期：1992.9

  Oxidation of the neurotoxin 6-aminodopamine (1) is known to proceed through the o-quinone 3, which undergoes intramolecular cyclisation to give 5,6-dihydroxyindole (6). In a re-examination of the reaction, we have found that at concentrations of 1 higher than 5 x 10(-3) M a quite different course prevails, leading to the formation of the novel 7-amino-8-(2-aminoethyl)-3-hydroxy-2-oxo-2,3,4,10-tetrahydro [3,4a] iminoethanophenoxazine (7). Product 7 was formed by aerobic, chemical (persulphate, periodate) or enzymatic (tyrosinase, peroxidase/H2O2) oxidation of 1. on acetylation, 7 afforded the tetraacetate 8. Oxidation of the model compound 5-amino-4-methylcatechol (9) proceeded similarly as that of 1, to give the tetrahydrophenoxazinedione 11.