2-<<2-(2-hydroxyphenyl)ethyl>amino>-1,4-naphthoquinone | 173912-74-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-<<2-(2-hydroxyphenyl)ethyl>amino>-1,4-naphthoquinone
• 英文别名: 2-[2-(2-Hydroxyphenyl)ethylamino]-1,4-naphthoquinone；2-[2-(2-hydroxyphenyl)ethylamino]naphthalene-1,4-dione
• CAS: 173912-74-8
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: MHQHXIGWANWXNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  513.6±50.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-<<2-(2-hydroxyphenyl)ethyl>amino>-1,4-naphthoquinone 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 三氟乙酸 为溶剂， 反应 0.5h， 生成 1,2,3,4,5,10-hexahydrobenzoquinoline-5,10-dione-4-spiro-1'-cyclohexa-3',5'-dien-2'-one
  参考文献：
  名称：

  An Intramolecular Cyclization of Phenol Derivatives Bearing Aminoquinones Using a Hypervalent Iodine Reagent

  摘要：

  The hypervalent iodine oxidation of phenol derivatives bearing aminoquinones at the ortho (9) or meta positions (19) in 2,2,2-trifluoroethanol was investigated with the aim of preparing novel antitumor compounds. Azacarbocyclic spirodienone derivatives (13) or phenol derivatives containing the 2,3-dihydro-1H-azepine systems (17, 20) were selectively obtained by the reaction of these phenol derivatives and the hypervalent io dine reagent, phenyliodine(III) bis(trifluoro acetate). The application of this reaction to phenol derivatives bearing aminoquinones (10-12) is also described.

  DOI：

  10.1021/jo951439q
• 作为产物：
  描述：

  1-benzyloxy-2-(2-nitrovinyl)benzene 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 乙醇 为溶剂， 反应 32.0h， 生成 2-<<2-(2-hydroxyphenyl)ethyl>amino>-1,4-naphthoquinone
  参考文献：
  名称：

  An Intramolecular Cyclization of Phenol Derivatives Bearing Aminoquinones Using a Hypervalent Iodine Reagent

  摘要：

  The hypervalent iodine oxidation of phenol derivatives bearing aminoquinones at the ortho (9) or meta positions (19) in 2,2,2-trifluoroethanol was investigated with the aim of preparing novel antitumor compounds. Azacarbocyclic spirodienone derivatives (13) or phenol derivatives containing the 2,3-dihydro-1H-azepine systems (17, 20) were selectively obtained by the reaction of these phenol derivatives and the hypervalent io dine reagent, phenyliodine(III) bis(trifluoro acetate). The application of this reaction to phenol derivatives bearing aminoquinones (10-12) is also described.

  DOI：

  10.1021/jo951439q