Benzoic acid (2aR,4S,4aS,6R,9R,10S,10aR,10bS)-6,10b-diacetoxy-9-hydroxy-7-[2-hydroxy-1-methyl-eth-(E)-ylidene]-4a,8,8-trimethyl-5-oxo-4-triethylsilanyloxy-dodecahydro-2-oxa-cyclobuta[3,4]benzo[1,2]cycloocten-10-yl ester | 423176-70-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: Benzoic acid (2aR,4S,4aS,6R,9R,10S,10aR,10bS)-6,10b-diacetoxy-9-hydroxy-7-[2-hydroxy-1-methyl-eth-(E)-ylidene]-4a,8,8-trimethyl-5-oxo-4-triethylsilanyloxy-dodecahydro-2-oxa-cyclobuta[3,4]benzo[1,2]cycloocten-10-yl ester
• 英文别名: [(1R,2S,5R,7S,8S,10R,11E,13R,14S)-2,10-diacetyloxy-13-hydroxy-11-(1-hydroxypropan-2-ylidene)-8,12,12-trimethyl-9-oxo-7-triethylsilyloxy-4-oxatricyclo[6.6.0.02,5]tetradecan-14-yl] benzoate
• CAS: 423176-70-9
• 化学式: C₃₆H₅₂O₁₁Si
• 分子量: 688.888
• InChiKey: UMPXVHOQMDDJCP-HIUGTYJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  48
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  155
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2aR,4S,4aS,6R,9R,10S,10aR,10bS)-6,10b-diacetoxy-9-hydroxy-7-[2-hydroxy-1-methyl-eth-(E)-ylidene]-4a,8,8-trimethyl-5-oxo-4-triethylsilanyloxy-dodecahydro-2-oxa-cyclobuta[3,4]benzo[1,2]cycloocten-10-yl ester 在 manganese(IV) oxide 作用下， 以 甲苯 为溶剂， 以98%的产率得到[(1R,2S,3R,4S,7R,9S,10S,12R)-4,12-diacetyloxy-10,14,17,17-tetramethyl-11,15-dioxo-9-triethylsilyloxy-6,16-dioxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
  参考文献：
  名称：

  Synthesis and Evaluation of 14-Nor-A-secotaxoids

  摘要：

  A series of 14-nor-A-secotaxoids has been prepared from 10-deacetyl-14beta-hydroxybaccatin III (3a) and some unexpected and new reactivity of the taxane system has been revealed. The observation that the final compounds were considerably less active than taxol and their 1,10-oxygen-bridged analogues shows that the 1,10-oxygen tether can partially compensate for the opening of ring A, and suggests that 14-nor-A-secotaxoids warrant further investigation as simplified taxol mimics.

  DOI：

  10.1002/1099-0690(20021)2002:2<277::aid-ejoc277>3.0.co;2-f
• 作为产物：
  描述：

  Benzoic acid (2aR,4S,4aS,6R,10S,10aR,10bS)-6,10b-diacetoxy-7-[2-hydroxy-1-methyl-eth-(E)-ylidene]-4a,8,8-trimethyl-5,9-dioxo-4-triethylsilanyloxy-dodecahydro-2-oxa-cyclobuta[3,4]benzo[1,2]cycloocten-10-yl ester 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以74%的产率得到Benzoic acid (2aR,4S,4aS,6R,9R,10S,10aR,10bS)-6,10b-diacetoxy-9-hydroxy-7-[2-hydroxy-1-methyl-eth-(E)-ylidene]-4a,8,8-trimethyl-5-oxo-4-triethylsilanyloxy-dodecahydro-2-oxa-cyclobuta[3,4]benzo[1,2]cycloocten-10-yl ester
  参考文献：
  名称：

  Synthesis and Evaluation of 14-Nor-A-secotaxoids

  摘要：

  A series of 14-nor-A-secotaxoids has been prepared from 10-deacetyl-14beta-hydroxybaccatin III (3a) and some unexpected and new reactivity of the taxane system has been revealed. The observation that the final compounds were considerably less active than taxol and their 1,10-oxygen-bridged analogues shows that the 1,10-oxygen tether can partially compensate for the opening of ring A, and suggests that 14-nor-A-secotaxoids warrant further investigation as simplified taxol mimics.

  DOI：

  10.1002/1099-0690(20021)2002:2<277::aid-ejoc277>3.0.co;2-f