N,N,O-Tris(2,2,2-trichloroethoxycarbonyl)-5-amino-12-hydroxy-4-methoxy-7-<(trimethylsilyl)oxy>-6a,7,8,9,10,10a-hexahydronaphthacene-6,9,11-trione | 134051-13-1

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: N,N,O-Tris(2,2,2-trichloroethoxycarbonyl)-5-amino-12-hydroxy-4-methoxy-7-<(trimethylsilyl)oxy>-6a,7,8,9,10,10a-hexahydronaphthacene-6,9,11-trione
• 英文别名: N,N,O-Tris(2,2,2-trichloroethoxycarbonyl)-5-amino-12-hydroxy-4-methoxy-7-[(trimethylsilyl)oxy]-6a,7,8,9,10,10a-hexahydronaphthacene-6,9,11-trione
• CAS: 134051-13-1；138584-01-7
• 化学式: C₃₁H₂₈Cl₉NO₁₂Si
• 分子量: 953.725
• InChiKey: BPKFGMSUHICZQV-WDYCEAGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.75
• 重原子数：
  54.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  161.04
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N,N,O-Tris(2,2,2-trichloroethoxycarbonyl)-5-amino-12-hydroxy-4-methoxy-7-<(trimethylsilyl)oxy>-6a,7,8,9,10,10a-hexahydronaphthacene-6,9,11-trione 在 potassium dihydrogenphosphate 、 硫酸 、 溶剂黄146 、 mercury(II) oxide 、 锌 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 0.33h， 生成 (+/-)-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
• 作为产物：
  描述：

  N,N,O-Tris(2,2,2-trichloroethoxycarbonyl)-5-amino-12-hydroxy-4-methoxy-7,9-bis<(trimethylsilyl)oxy>-6a,7,10,10a-tetrahydronaphthacene-6,11-dione 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以92%的产率得到N,N,O-Tris(2,2,2-trichloroethoxycarbonyl)-5-amino-12-hydroxy-4-methoxy-7-<(trimethylsilyl)oxy>-6a,7,8,9,10,10a-hexahydronaphthacene-6,9,11-trione
  参考文献：
  名称：

  Total synthesis of (±)-5-iminodaunomycinone and (±)-4-demethoxy-5-iminodaunomycinone

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)74501-1