[(1R,2R,6R,7S,10R)-2-(benzenesulfonyl)-1-butyl-10-[tert-butyl(dimethyl)silyl]oxy-7-methyl-3,5-dioxo-4-phenyl-4-azatricyclo[5.2.2.02,6]undec-8-en-8-yl] acetate | 1312542-14-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(1R,2R,6R,7S,10R)-2-(benzenesulfonyl)-1-butyl-10-[tert-butyl(dimethyl)silyl]oxy-7-methyl-3,5-dioxo-4-phenyl-4-azatricyclo[5.2.2.02,6]undec-8-en-8-yl] acetate
• CAS: 1312542-14-5
• 化学式: C₃₅H₄₅NO₇SSi
• 分子量: 651.896
• InChiKey: HJMRMCHKNIXGRJ-CGUCTSAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.83
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  [(4R)-5-butyl-4-[tert-butyl(dimethyl)silyl]oxy-2-methylcyclohexa-1,5-dien-1-yl] acetate 、 3-(Benzenesulfonyl)-1-phenylpyrrole-2,5-dione 以 二氯甲烷 为溶剂， 反应 24.0h， 以97%的产率得到[(1R,2R,6R,7S,10R)-2-(benzenesulfonyl)-1-butyl-10-[tert-butyl(dimethyl)silyl]oxy-7-methyl-3,5-dioxo-4-phenyl-4-azatricyclo[5.2.2.02,6]undec-8-en-8-yl] acetate
  参考文献：
  名称：

  Controlling the Facial Selectivity of Asymmetric [4 + 2] Cyclo-additions: A Concise Synthesis of the cis-Decalin Core Structure of Superstolides A and B

  摘要：

  Reglo-, stereo-, and facial selective [4 + 2] cycloadditions between highly activated vinyl sulfones and 1,3-dienes derived from (R)-4-tert-wbutyldimethylsilyloxy-2-cyclohexen-1-one provide a powerful approach for the asymmetric synthesis of compounds containing the bicyclo[2.2.2]octanone carbon skeleton. This new methodology has been successfully applied to the asymmetric synthesis of the cis-decalin core structure of the potent anticancer marine natural products superstolides A and B.

  DOI：

  10.1021/ol201095b