Acetic acid (1R,6aS,12aR,12bR)-12a-bromo-1-(tert-butyl-dimethyl-silanyloxy)-7,12-dioxo-1,2,3,4,6,6a,7,12,12a,12b-decahydro-benzo[a]anthracen-8-yl ester | 143733-95-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: Acetic acid (1R,6aS,12aR,12bR)-12a-bromo-1-(tert-butyl-dimethyl-silanyloxy)-7,12-dioxo-1,2,3,4,6,6a,7,12,12a,12b-decahydro-benzo[a]anthracen-8-yl ester
• 英文别名: [(1R,6aS,12aR,12bR)-12a-bromo-1-[tert-butyl(dimethyl)silyl]oxy-7,12-dioxo-2,3,4,6,6a,12b-hexahydro-1H-benzo[a]anthracen-8-yl] acetate
• CAS: 143733-95-3
• 化学式: C₂₆H₃₃BrO₅Si
• 分子量: 533.535
• InChiKey: SMLNGPAYDIPTTL-AVVAAUGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.26
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Acetic acid (1R,6aS,12aR,12bR)-12a-bromo-1-(tert-butyl-dimethyl-silanyloxy)-7,12-dioxo-1,2,3,4,6,6a,7,12,12a,12b-decahydro-benzo[a]anthracen-8-yl ester 在 四丁基氟化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 0.17h， 生成 Acetic acid (1R,4aR,12bS)-1-(tert-butyl-dimethyl-silanyloxy)-4a-hydroxy-7,12-dioxo-1,2,3,4,4a,7,12,12b-octahydro-benzo[a]anthracen-8-yl ester
  参考文献：
  名称：

  Synthetic studies of the angucycline antibiotics. Reaction of a quinone methide produced from a benz[a]anthracene with molecular oxygen

  摘要：

  Molecular oxygen-based procedures for the stereocontrolled introduction of oxygen functionality present in the antitumor antibiotics aquayamycin (1) and SF 2315B (2) are described.

  DOI：

  10.1021/jo00047a001
• 作为产物：
  描述：

  5-acetoxy-2-bromo-1,4-naphthoquinone 、 3-<(tert-Butyldimethylsilyl)oxy>-1-vinylcyclohexene 以 甲苯 为溶剂， 反应 12.0h， 以74%的产率得到Acetic acid (1R,6aS,12aR,12bR)-12a-bromo-1-(tert-butyl-dimethyl-silanyloxy)-7,12-dioxo-1,2,3,4,6,6a,7,12,12a,12b-decahydro-benzo[a]anthracen-8-yl ester
  参考文献：
  名称：

  Synthetic Studies of the Angucycline Antibiotics. Stereocontrolled Assembly of the SF 2315B Ring System

  摘要：

  The stereocontrolled assembly of epoxy quinol 2 is described. Diels-Alder cycloaddition between 2-bromo-5-acetoxyjuglone (5) and 3-[(triisopropylsilyl)oxy]-1-vinylcyclohexene (6c) followed by saponification provided quinone 11b in good overall yield. Oxygenation of a tetrahydrofuran solution of 11b in the presence of tetrabutylammonium fluoride resulted in the production of epoxy alcohols alpha-12b and alpha-13b. Epoxy alcohol alpha-12b was converted to epoxy quinol 2 in five steps. A key transformation of the latter reaction sequence was a C1 hydroxyl-directed reduction of the C12 keto group (20 --> 21). The assigned structure of 2 was confirmed by single-crystal X-ray analysis.

  DOI：

  10.1021/jo00126a043