4-amino-5-methyl-1,2-benzoquinone | 145069-21-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-amino-5-methyl-1,2-benzoquinone
• 英文别名: 4-amino-5-methyl-[1,2]benzoquinone；4-Amino-5-methyl-[1,2]benzochinon；4-Amino-5-methylcyclohexa-3,5-diene-1,2-dione
• CAS: 145069-21-2
• 化学式: C₇H₇NO₂
• mdl: MFCD19206841
• 分子量: 137.138
• InChiKey: OQGAWMSOAXSPOM-UHFFFAOYSA-N

物化性质

• 沸点：
  217.3±33.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  60.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-amino-5-methyl-1,2-benzoquinone 、 4-amino-5-methylcatechol hydrochloride 以 甲醇 为溶剂， 反应 12.0h， 以30%的产率得到7-amino-4a,8-dimethyl-4,10-dihydrophenoxazine-2,3-dione
  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：

  4-amino-5-methyl-pyrocatechol 在 氧气 作用下， 生成 4-amino-5-methyl-1,2-benzoquinone
  参考文献：
  名称：

  Horner; Sturm, Justus Liebigs Annalen der Chemie, 1957, vol. 608, p. 128,131, 137

  摘要：

  DOI：

文献信息

• Horner; Sturm, Justus Liebigs Annalen der Chemie, 1957, vol. 608, p. 128,131, 137
  作者：Horner、Sturm

  DOI：——

  日期：——
• 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.