7-deoxydaunomycinone quinone methide | 85337-17-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 7-deoxydaunomycinone quinone methide
• 英文别名: (9R)-9-acetyl-6,9,11,12-tetrahydroxy-4-methoxy-8,10-dihydrotetracen-5-one
• CAS: 85337-17-3
• 化学式: C₂₁H₁₈O₇
• 分子量: 382.37
• InChiKey: BJYSTWTYWUWOCA-OAQYLSRUSA-N

物化性质

• 沸点：
  728.8±60.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.41
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  124.29
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  7-deoxydaunomycinone quinone methide 在 三羟甲基氨基甲烷盐酸盐 、 3,5,5-trimethyl-2-oxomorpholin-3-yl 、 三羟甲基氨基甲烷 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 生成 7-deoxydaunomycinone hydroquinone
  参考文献：
  名称：

  Mechanistic investigation of reduction of daunomycin and 7-deoxydaunomycinone with bi(3,5,5-trimethyl-2-oxomorpholin-3-yl)

  摘要：

  DOI：

  10.1021/ja00320a027
• 作为产物：
  描述：

  道诺霉素氢醌 以 水 为溶剂， 生成 7-deoxydaunomycinone quinone methide
  参考文献：
  名称：

  Leuco daunomycin, a tautomer of daunomycin hydroquinone

  摘要：

  DOI：

  10.1021/ja00185a066

文献信息

• Electrophilic trapping of the tautomer of 7-deoxydaunomycinone. A possible mechanism for covalent binding of daunomycin to DNA
  作者：Don L. Kleyer、Tad H. Koch

  DOI：10.1021/ja00353a062

  日期：1983.7
• Gaudiano, Giorgio; Koch, Tad H., Journal of the American Chemical Society, 1990, vol. 112, # 25, p. 9423 - 9425
  作者：Gaudiano, Giorgio、Koch, Tad H.

  DOI：——

  日期：——
• Schweitzer, Barbara Ann; Egholm, Michael; Koch, Tad H., Journal of the American Chemical Society, 1992, vol. 114, # 1, p. 242 - 248
  作者：Schweitzer, Barbara Ann、Egholm, Michael、Koch, Tad H.

  DOI：——

  日期：——
• Synthesis and redox chemistry of 5-deoxydaunomycin. A long-lived hydroquinone tautomer
  作者：Barbara Ann Schweitzer、Tad H. Koch

  DOI：10.1021/ja00066a012

  日期：1993.6

  Reduction of 5-iminodaunomycin with dithionite in anaerobic methanol followed by lowering the pH to 3 and saturating with air led to deamination without glycosidic cleavage to yield 89% 5-deoxydaunomycin. An intermediate observed during the reaction is proposed to be the hydroquinone tautomer, 8-acetyl-12-amino-10-[(3-amino-2,3,6-trideoxy-alpha-lyxo-hexopyranosyl)oxy]-1-methoxy-7,9,10,12-tetrahydro-6,8,11-trihydroxy-5(8H)-naphthacenone hydrochloride (1), which loses ammonia with a half-life of 49 min. Anaerobic reduction of 5-deoxydaunomycin with bi(3,5,5-trimethyl-2-oxomorpholin-3-yl) (TM-3 dimer) in methanol buffered to an apparent pH of 8 yielded 26% recovered 5-deoxydaunomycin, 56% 5,7-dideoxydaunomycinone, and 18% 2-acetyl-11-hydroxy-7-methoxy-5,12-naphthacenedione (5) after 42 h and subsequent exposure to molecular oxygen. The reduction leads to relatively rapid formation of a long-lived transient proposed to be, 8-acetyl-10-[(3-amino-2,3,6-trideoxy-a-lyxo-hexopyranosyl)oxy]-l-methoxy-7,9,10,12-tetrahydro-6,8,11-trihydroxy-5(8H)-naphthacenone (4). Exposure of 4 at its maximum concentration to molecular oxygen yielded 88% recovered 5-deoxydaunomycin and 12% 5. Tetrahydronaphthacenone 4 disappeared with a half-life of 2283 min in the absence of oxygen and 16 min in air-saturated methanol. Mechanistic pathways to the products are proposed in Scheme II. Analysis of the apparent rate constants for disappearance of 4 indicates that 5-deoxydaunomycin undergoes glycosidic cleavage to its 7-deoxyaglycon 8000 times slower than daunomycin upon reduction to the hydroquinone state.
• Spectroscopic observation of the tautomer of 7-deoxydaunomycinone from elimination of daunosamine from daunomycin hydroquinone
  作者：Don L. Kleyer、Tad H. Koch

  DOI：10.1021/ja00346a083

  日期：1983.4