(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 | 1312542-20-3

• 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: (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
• CAS: 1312542-20-3
• 化学式: C₂₉H₄₇NO₄Si₂
• 分子量: 529.867
• InChiKey: YCYZHUZLKAUCGU-ZYQWIPQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.16
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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 、 potassium fluoride 、 四丁基氟化铵 、 水 、 双氧水 、 tetramethylammonium borohydride 、 potassium hydride 、 双(三甲基硅烷基)氨基钾 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 甲醇 、 二乙二醇二甲醚 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 97.0h， 生成 (3R,3aS,5aR,6S,8S,9aR,9bR)-6-hydroxy-8-methoxy-9b-methyl-2-phenyl-3-propan-2-yloxy-3,3a,5a,6,7,8,9,9a-octahydrobenzo[g]isoindol-1-one
  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,2R,3S,6S,8S,10R,11R)-3-(benzenesulfonyl)-11-[tert-butyl(dimethyl)silyl]oxy-8-hydroxy-5-phenyl-7-oxa-5-azatetracyclo[6.4.0.02,6.03,10]dodecan-4-one 在 2,6-二甲基吡啶 、 六甲基磷酰三胺 、 samarium diiodide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.83h， 生成 (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
  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

文献信息

• Controlling the Facial Selectivity of Asymmetric [4 + 2] Cyclo-additions: A Concise Synthesis of the <i>cis</i>-Decalin Core Structure of Superstolides A and B
  作者：Lei Chen、Zhengmao Hua、Gangqin Li、Zhendong Jin

  DOI：10.1021/ol201095b

  日期：2011.7.15

  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.