4-Amino-5-methoxy-2-tert.butylphenol | 36150-68-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-Amino-5-methoxy-2-tert.butylphenol
• 英文别名: 4-Amino-2-tert-butyl-5-methoxyphenol
• CAS: 36150-68-2
• 化学式: C₁₁H₁₇NO₂
• 分子量: 195.261
• InChiKey: LKBGPBOPFVIPDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-叔-丁基苯-1,3-二醇 在 dipotassium hydrogenphosphate 、 potassium nitrososulfonate 、 硫酸 、 苄胺 作用下， 以 乙醇 、 水 为溶剂， 反应 3.03h， 生成 4-Amino-5-methoxy-2-tert.butylphenol
  参考文献：
  名称：

  Model Studies of Topaquinone-Dependent Amine Oxidases. 1. Oxidation of Benzylamine by Topaquinone Analogs

  摘要：

  The aerobic oxidation of benzylamine by model compounds of topaquinone, the active site organic cofactor in copper-containing amine oxidases, was studied in order to elucidate the chemical function of the cofactor in substrate oxidation. In this study, topaquinone hydantoin (1(ox)) and a series of 2-hydroxy-5-alkyl-1,4-benzoquinones which differ in the bulk of their alkyl substituent (5, 6, 7, and 8) were employed as model compounds of the cofactor. The p-quinones (9, 10, 11, and 12) and the o-quinones (13 and 14) were prepared in order to compare them to the topaquinone analogs. Benzylamine was oxidized by the topaquinone analogs (1(ox), 5, 6, 7, and 8) to yield N-benzylidenebenzylamine (PhCH=NCH(2)Ph) as a sole product in acetonitrile at room temperature, The quinones bearing a bulky substituent (1(ox), 5, and 6) were found to be more efficient catalysts than those bearing a small primary alkyl group (7 and 8). In the latter case, the dimers (16 and 17) of the substrate Schiff base intermediates (15, R = methyl, ethyl) were isolated. The p-quinones (9, 10, 11, and 12) were catalytically inactive, The o-quinones (13 and 14) had detectable catalytic activity at room temperature, In anaerobic reactions of the o-quinones (13 and 14) with benzylamine, quantitative formation of the product (PhCH=NCH(2)Ph) was observed. For both o-quinones, products and intermediates which support a transamination mechanism were identified by H-1 NMR spectroscopy. The order of reactivity of quinones (5 > 14 > 13) reflects their redox potentials, such that regeneration of quinone may be rate-determining with o-quinones. These results demonstrate a substantial role of the 2-hydroxyl group of the topaquinone in preventing the formation of Michael adducts with substrate amine and in facilitating the reoxidation of aminoresorcinol intermediates.

  DOI：

  10.1021/ja00139a002