9-氨基-10-羟基蒽-1,4-二酮 | 96502-05-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 9-氨基-10-羟基蒽-1,4-二酮
• 英文名称: 1,4-dihydroxy-9,10-anthraquinone monoimine
• 英文别名: 1,4-dihydroxy-9,10-anthraquinone imine；9-Amino-10-hydroxy-1,4-anthraquinone；1,4-dihydroxy-10-iminoanthracen-9-one
• CAS: 96502-05-5
• 化学式: C₁₄H₉NO₃
• 分子量: 239.23
• InChiKey: QDVAZOQVPMEHLF-UHFFFAOYSA-N

物化性质

• 沸点：
  466.1±45.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-氨基-10-羟基蒽-1,4-二酮 在 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 23.0h， 生成 N,N,O-Tris(ethoxycarbonyl)-5-amino-12-hydroxy-10-<(trimethylsilyl)oxy>-6a,7,10,10a-tetrahydronaphthacene-6,11-dione
  参考文献：
  名称：

  Polycyclic hydroxy quinones. 28. Synthesis and Diels-Alder reactions of N,N,O-triacyl derivatives of 10-amino-9-hydroxy-1,4-anthraquinones. An efficient, regiospecific synthesis of (.+-.)-5-iminodaunomycinone, (.+-.)-4-demethoxy-5-iminodaunomycinone, and (.+-.)-daunomycinone

  摘要：

  The development of a general strategy for the construction of anthracyclinones based on a Diels-Alder reaction of substituted derivatives of 10-amino-9-hydroxy-1,4-anthraquinone is described. The key stages are (i) formation of N,O,O-triacyl derivatives of 1,4-dihydroxy-9,10-anthraquinone monoimines in a tautomer specific fashion, (ii) transacylation into N,N,O-triacyl derivatives of the corresponding 10-amino-9-hydroxy-1,4-anthraquinone, and (iii) Diels-Alder reaction with an appropriately substituted 1,3-diene regiocontrolled by steric factors. This strategy has been applied to the total synthesis of (+/-)-5-iminodaunomycinone (4) and (+/-)-4-demethoxy-5-iminodaunomycinone (3) and to a novel and short synthesis of (+/-)-daunomycinone (5).

  DOI：

  10.1021/jo00078a019
• 作为产物：
  描述：

  (4-乙酰氧基-9,10-二氧代蒽-1-基)乙酸酯 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 144.0h， 生成 9-氨基-10-羟基蒽-1,4-二酮
  参考文献：
  名称：

  Synthesis, tautomerism and diels-alder reactions of 1, 4-dihydroxy-9, 10-anthraquinon-9-imines

  摘要：

  DOI：

  10.1016/s0040-4039(00)98481-8

文献信息

• Polycyclic hydroxyquinones. XXVII. Tautomerism in 1,4-Dihydroxy-9,10-anthraquinone Monoimines. Cycloaddition Reactions of Their 1,4-Anthraquinonoid Tautomers
  作者：Francisco Fariña、M.Teresa Molina、Pedro Noheda、M.Carmen Paredes

  DOI：10.1016/s0040-4020(01)86592-3

  日期：1992.9

  substituted derivatives thereof (6a-i) have been prepared by ammonolysis of the corresponding 1,4-dihydroxy-9,10-anthraquinones. 1H- and 13C-n.m.r. studies show the existence of a rapid tautomeric equilibrium in quinone imines of type 6. Diels-Alder reaction with the 1,4-anthraquinonoid tautomer of quinone monoimines 6a,e affords ABCD tetracyclic systems related to those existing in anthracyclinones.

  通过氨解相应的1，4-二羟基-9，10-蒽醌，制备了1，4-二羟基-9，10-蒽醌单亚胺及其不同取代的衍生物（6a-i）。1 H和13 C-nmr研究表明，在6型醌亚胺中存在快速的互变异构平衡。与醌单亚胺6a，e的1,4-蒽醌类互变异构体进行Diels-Alder反应，可得到与蒽环类化合物中存在的ABCD四环体系相关的ABCD四环体系。
• Total synthesis of (±)-5-iminodaunomycinone and (±)-4-demethoxy-5-iminodaunomycinone
  作者：Francisco Fariña、Pedro Noheda、M.Carmen Paredes

  DOI：10.1016/s0040-4039(00)74501-1

  日期：1991.2

  The total synthesis of (+/-)-5-iminodaunomycinone (4a) and (+/-)-4-demethoxy-5-iminodaunomycinone (4b) has been achieved from the readily available 5-methoxy-1,4-dihydroxy-9,10-anthraquinone (5a) and 1,4-dihydroxy-9,10-anthraquinone (5b), respectively. A short and convenient synthesis of (+/-)-daunomycinone (4c) has also been achieved by acid hydrolysis of 4a.
• POPOV S. I.; VLOSENKO V. P., ZH. ORGAN. XIMII, 1981, 17, HO 2, 444-445
  作者：POPOV S. I.、 VLOSENKO V. P.

  DOI：——

  日期：——