(3S,4R)-4-(4-Methoxy-benzoyl)-3-(2-trimethylsilanylmethyl-allyl)-tetrahydro-pyran-2-one | 181588-36-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4R)-4-(4-Methoxy-benzoyl)-3-(2-trimethylsilanylmethyl-allyl)-tetrahydro-pyran-2-one
• 英文别名: (3S,4R)-4-(4-methoxybenzoyl)-3-[2-(trimethylsilylmethyl)prop-2-enyl]oxan-2-one
• CAS: 181588-36-3
• 化学式: C₂₀H₂₈O₄Si
• 分子量: 360.525
• InChiKey: BWVZOSCVGHWXSE-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4R)-4-(4-Methoxy-benzoyl)-3-(2-trimethylsilanylmethyl-allyl)-tetrahydro-pyran-2-one 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以80%的产率得到(4aR,5S,8aS)-5-Hydroxy-5-(4-methoxy-phenyl)-7-methylene-octahydro-isochromen-1-one
  参考文献：
  名称：

  Enantioselective synthesis of unsubstituted and 3-substituted-4-aroyl-δ-lactones. Easy way to enantiopure bicyclic lactone systems

  摘要：

  Michael addition of lithiated chiral aminonitriles 1a,b to alpha,beta-unsaturated lactone 2 afforded (4R)-aroyl-delta-lactones 8a,b with a ee value greater than or equal to 99%. Michael addition I subsequent alpha alkylation process gave the corresponding (3S)-substituted-(4R)-aroyl-delta-lactones 9-10a, 9b with a ee value of 66 up to 87% and 11-12a with high enantiomeric purity the ee being greater than or equal to 99%. The absolute configuration of the Michael adduct 7a was established by X-ray analysis and as a result that of all the other compounds was assigned. Lewis acid catalyzed cyclization of (3S,4R)-12a provided the enantiomerically pure hydroxy bicyclic lactone (4aR,5S,8aS)-13a. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4020(96)00542-x
• 作为产物：
  描述：

  2-(碘甲基)丙-2-烯基-三甲基硅烷 在 正丁基锂 、 silver nitrate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.0h， 生成 (3S,4R)-4-(4-Methoxy-benzoyl)-3-(2-trimethylsilanylmethyl-allyl)-tetrahydro-pyran-2-one
  参考文献：
  名称：

  Enantioselective synthesis of unsubstituted and 3-substituted-4-aroyl-δ-lactones. Easy way to enantiopure bicyclic lactone systems

  摘要：

  Michael addition of lithiated chiral aminonitriles 1a,b to alpha,beta-unsaturated lactone 2 afforded (4R)-aroyl-delta-lactones 8a,b with a ee value greater than or equal to 99%. Michael addition I subsequent alpha alkylation process gave the corresponding (3S)-substituted-(4R)-aroyl-delta-lactones 9-10a, 9b with a ee value of 66 up to 87% and 11-12a with high enantiomeric purity the ee being greater than or equal to 99%. The absolute configuration of the Michael adduct 7a was established by X-ray analysis and as a result that of all the other compounds was assigned. Lewis acid catalyzed cyclization of (3S,4R)-12a provided the enantiomerically pure hydroxy bicyclic lactone (4aR,5S,8aS)-13a. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4020(96)00542-x