(4aS,5S,8S,8aS)-5-(2-Hydroxy-ethyl)-5,8a-dimethyl-6-methylene-8-trimethylsilanyl-octahydro-naphthalen-1-one | 199525-22-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aS,5S,8S,8aS)-5-(2-Hydroxy-ethyl)-5,8a-dimethyl-6-methylene-8-trimethylsilanyl-octahydro-naphthalen-1-one
• CAS: 199525-22-9
• 化学式: C₁₈H₃₂O₂Si
• 分子量: 308.536
• InChiKey: RSQHOXYLKKPHHA-OWLYRPNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4aS,5S,8S,8aS)-5-(2-Hydroxy-ethyl)-5,8a-dimethyl-6-methylene-8-trimethylsilanyl-octahydro-naphthalen-1-one 在 Wilkinson's catalyst 咪唑 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 dimethyl sulfide borane 、 三氟化硼 、 碘 、 三苯基膦 作用下， 以 乙醚 、 二氯甲烷 、 苯 为溶剂， -78.0~65.0 ℃ 、6.89 MPa 条件下， 反应 48.5h， 生成
  参考文献：
  名称：

  Total Synthesis of Dysidiolide

  摘要：

  The cdc25A protein phosphatase inhibitor dysidiolide (1) has been synthesized enantioselectively, starting from the enantiomerically pure ketal enone 2 and using a cationic rearrangement as the key step to produce the fully substituted bicyclic core of the natural product. Once the central portion of 1 was established, elaboration of the side chains was accomplished expediently via steps that included (1) vinyl cuprate displacement of an iodide to complete the C-l side chain, (2) a highly diastereoselective oxazaborolidine-catalyzed (CBS) reduction to form carbinol 11, and (3) photochemical oxidation of 11 to generate the gamma-hydroxybutenolide functionality of 1. Additionally, this synthesis proves the absolute stereochemistry of dysidiolide (1).

  DOI：

  10.1021/ja973023v
• 作为产物：
  描述：

  (4aS,5S,8S,8aS)-(+)-3,4,4a,5,6,7,8,8a-octahydro-5-(2-hydroxyethyl)-6-methenyl-5,8a-dimethyl-8-trimethylsilylnaphthalen-1(2H)-one 1-(ethylene acetal) 在 4-甲基苯磺酸吡啶 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 以100%的产率得到(4aS,5S,8S,8aS)-5-(2-Hydroxy-ethyl)-5,8a-dimethyl-6-methylene-8-trimethylsilanyl-octahydro-naphthalen-1-one
  参考文献：
  名称：

  Total Synthesis of Dysidiolide

  摘要：

  The cdc25A protein phosphatase inhibitor dysidiolide (1) has been synthesized enantioselectively, starting from the enantiomerically pure ketal enone 2 and using a cationic rearrangement as the key step to produce the fully substituted bicyclic core of the natural product. Once the central portion of 1 was established, elaboration of the side chains was accomplished expediently via steps that included (1) vinyl cuprate displacement of an iodide to complete the C-l side chain, (2) a highly diastereoselective oxazaborolidine-catalyzed (CBS) reduction to form carbinol 11, and (3) photochemical oxidation of 11 to generate the gamma-hydroxybutenolide functionality of 1. Additionally, this synthesis proves the absolute stereochemistry of dysidiolide (1).

  DOI：

  10.1021/ja973023v