N,N,O-Tris(tert-butoxycarbonyl)-10-amino-9-hydroxy-5-methoxy-1,4-anthraquinone | 152899-86-0

• 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(tert-butoxycarbonyl)-10-amino-9-hydroxy-5-methoxy-1,4-anthraquinone
• 英文别名: [10-[Bis[(2-methylpropan-2-yl)oxycarbonyl]amino]-5-methoxy-1,4-dioxoanthracen-9-yl] tert-butyl carbonate
• CAS: 152899-86-0
• 化学式: C₃₀H₃₅NO₁₀
• 分子量: 569.609
• InChiKey: VFHPVLIIACIZRB-UHFFFAOYSA-N

物化性质

• 沸点：
  685.1±65.0 °C(predicted)
• 密度：
  1.262±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (E)-1,3-bis(trimethylsilyloxy)buta-1,3-diene 、 N,N,O-Tris(tert-butoxycarbonyl)-10-amino-9-hydroxy-5-methoxy-1,4-anthraquinone 以 甲苯 为溶剂， 反应 12.0h， 以96%的产率得到N,N,O-Tris(tert-butoxycarbonyl)-5-amino-12-hydroxy-4-methoxy-7,9-bis<(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：

  1,4-dihydroxy-5-methoxy-9,10-anthraquinone-10-imine 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.08h， 生成 N,N,O-Tris(tert-butoxycarbonyl)-10-amino-9-hydroxy-5-methoxy-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