O-((1R,3aR,4S,5R,7S,7aS)-1-isopropoxy-3a-methyl-3,8-dioxo-2-phenyloctahydro-1H-4,7-ethanoisoindol-5-yl) O-(p-tolyl) carbonothioate | 1312542-24-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: O-((1R,3aR,4S,5R,7S,7aS)-1-isopropoxy-3a-methyl-3,8-dioxo-2-phenyloctahydro-1H-4,7-ethanoisoindol-5-yl) O-(p-tolyl) carbonothioate
• CAS: 1312542-24-7
• 化学式: C₂₈H₃₁NO₅S
• 分子量: 493.624
• InChiKey: IOJULPCDWGQBDH-ZRACTAMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  35.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  O-((1R,3aR,4S,5R,7S,7aS)-1-isopropoxy-3a-methyl-3,8-dioxo-2-phenyloctahydro-1H-4,7-ethanoisoindol-5-yl) O-(p-tolyl) carbonothioate 反应 2.0h， 以92%的产率得到(1R,2R,5R,6S,7S)-2-methyl-4-phenyl-5-propan-2-yloxy-4-azatricyclo[5.2.2.02,6]undec-10-ene-3,8-dione
  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
• 作为产物：
  描述：

  (1S,2S,3R,6S,8R,10S,11R)-11-[tert-butyl(dimethyl)silyl]oxy-3-methyl-5-phenyl-8-triethylsilyloxy-7-oxa-5-azatetracyclo[6.4.0.02,6.03,10]dodecan-4-one 在 吡啶 、 盐酸 作用下， 反应 78.0h， 生成 O-((1R,3aR,4S,5R,7S,7aS)-1-isopropoxy-3a-methyl-3,8-dioxo-2-phenyloctahydro-1H-4,7-ethanoisoindol-5-yl) O-(p-tolyl) carbonothioate
  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