N,N,O-Tris(ethoxycarbonyl)-10-amino-9-hydroxy-1,4-anthraquinone | 152899-89-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: N,N,O-Tris(ethoxycarbonyl)-10-amino-9-hydroxy-1,4-anthraquinone
• 英文别名: [10-[Bis(ethoxycarbonyl)amino]-1,4-dioxoanthracen-9-yl] ethyl carbonate
• CAS: 152899-89-3
• 化学式: C₂₃H₂₁NO₉
• 分子量: 455.421
• InChiKey: SAIOVCDBTSJXPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N,N,O-Tris(ethoxycarbonyl)-10-amino-9-hydroxy-1,4-anthraquinone 在 盐酸 、 双氧水 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 43.0h， 生成 N,N,O-Tris(ethoxycarbonyl)-5-amino-7,12-dihydroxy-6a,7,8,9,10,10a-hexahydronaphthacene-6,9,11-trione
  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：

  N,O,O-Tris(ethoxycarbonyl)-1,4-dihydroxy-9,10-anthraquinone monoimine 以 甲苯 为溶剂， 反应 5.0h， 以93%的产率得到N,N,O-Tris(ethoxycarbonyl)-10-amino-9-hydroxy-1,4-anthraquinone
  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

• 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
  作者：Francisco Farina、Pedro Noheda、M. Carmen Paredes

  DOI：10.1021/jo00078a019

  日期：1993.12

  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).