(+/-)-4-Demethoxy-5-iminodaunomycinone | 138569-40-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: (+/-)-4-Demethoxy-5-iminodaunomycinone
• 英文别名: (+/-)-4-demethoxy-5-iminodaumycinone；(8R,10R)-8-acetyl-6,8,10,11-tetrahydroxy-12-imino-9,10-dihydro-7H-tetracen-5-one
• CAS: 138569-40-1
• 化学式: C₂₀H₁₇NO₆
• 分子量: 367.358
• InChiKey: XEQPKPVXWUTBJZ-MPBGBICISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  139
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N,N,O-Tris(2,2,2-trichloroethoxycarbonyl)-10-amino-9-hydroxy-1,4-anthraquinone 在 盐酸 、 potassium dihydrogenphosphate 、 硫酸 、 溶剂黄146 、 mercury(II) oxide 、 锌 作用下， 以 四氢呋喃 、 丙酮 、 苯 为溶剂， 反应 24.41h， 生成 (+/-)-4-Demethoxy-5-iminodaunomycinone
  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

文献信息

• 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.