(1S,2R,5R,6S,7S,10R)-10-hydroxy-2-methyl-4-phenyl-5-propan-2-yloxy-4-azatricyclo[5.2.2.02,6]undecane-3,8-dione | 1312542-22-5

• 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,2R,5R,6S,7S,10R)-10-hydroxy-2-methyl-4-phenyl-5-propan-2-yloxy-4-azatricyclo[5.2.2.02,6]undecane-3,8-dione
• CAS: 1312542-22-5
• 化学式: C₂₀H₂₅NO₄
• 分子量: 343.423
• InChiKey: FHUOZAJAQVMZCX-LYFZXNACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2R,5R,6S,7S,10R)-10-hydroxy-2-methyl-4-phenyl-5-propan-2-yloxy-4-azatricyclo[5.2.2.02,6]undecane-3,8-dione 在 吡啶 、 tetramethylammonium borohydride 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 二乙二醇二甲醚 、 水 、 甲苯 为溶剂， 反应 10.0h， 生成 (3R,3aS,5aR,6S,8S,9aR,9bR)-6-(dimethyl(phenyl)silyl)-8-hydroxy-3-isopropoxy-9b-methyl-2-phenyl-2,3,3a,5a,6,7,8,9,9a,9b-decahydro-1H-benzo[e]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 、 盐酸 、 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 74.83h， 生成 (1S,2R,5R,6S,7S,10R)-10-hydroxy-2-methyl-4-phenyl-5-propan-2-yloxy-4-azatricyclo[5.2.2.02,6]undecane-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