(1S,5S,6S,7S)-7-hydroxy-5-(methoxymethoxymethyl)-8,8-dimethyl-2-oxabicyclo[4.2.0]octan-3-one | 952101-34-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1S,5S,6S,7S)-7-hydroxy-5-(methoxymethoxymethyl)-8,8-dimethyl-2-oxabicyclo[4.2.0]octan-3-one
• CAS: 952101-34-7
• 化学式: C₁₂H₂₀O₅
• 分子量: 244.288
• InChiKey: XUICRILQEXRKJB-PXIYARARSA-N

物化性质

• 沸点：
  361.1±32.0 °C(predicted)
• 密度：
  1.148±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,5S,6S,7S)-7-hydroxy-5-(methoxymethoxymethyl)-8,8-dimethyl-2-oxabicyclo[4.2.0]octan-3-one 在 吡啶 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 (1S,5S,6R)-5-(methoxymethoxymethyl)-8,8-dimethyl-2-oxabicyclo[4.2.0]octan-3-one
  参考文献：
  名称：

  Pestalotiopsin A. Enantioselective Construction of Potential Building Blocks Derived from Antipodal Cyclobutanol Intermediates

  摘要：

  [GRAPHICS]D-Glyceraldehyde acetonide has been used as the starting point for accessing the enantiomeric cyclobutanols 11 in optically pure condition. The dextrorotatory enantiomer has been transformed in five steps into the [3.2.0] bicyclic lactone 22. While the deoxygenation of 22 proved to be problematical, the uncyclized variant 25 underwent the Barton process smoothly. These findings guided the related conversion of (-)-11 into 34. Use was also made of ring-closing metathesis to bring about the conversion of (+)-11 into [4.2.0] bicyclic lactone building blocks. In general, all three pathways are efficient and offer the prospect of practical side-chain appendage for the purpose of installing the nine-membered ring of pestalotiopsin A (1).

  DOI：

  10.1021/jo070861r
• 作为产物：
  描述：

  (1S,6S,7S)-7-benzyloxy-8,8-dimethyl-2-oxabicyclo[4.2.0]oct-4-en-3-one 在 palladium on activated charcoal sodium tetrahydroborate 、 copper(l) iodide 、 四甲基乙二胺 、 氢气 、 四丁基碘化铵 、 臭氧 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， -78.0~20.0 ℃ 、3.45 MPa 条件下， 反应 73.25h， 生成 (1S,5S,6S,7S)-7-hydroxy-5-(methoxymethoxymethyl)-8,8-dimethyl-2-oxabicyclo[4.2.0]octan-3-one
  参考文献：
  名称：

  Pestalotiopsin A. Enantioselective Construction of Potential Building Blocks Derived from Antipodal Cyclobutanol Intermediates

  摘要：

  [GRAPHICS]D-Glyceraldehyde acetonide has been used as the starting point for accessing the enantiomeric cyclobutanols 11 in optically pure condition. The dextrorotatory enantiomer has been transformed in five steps into the [3.2.0] bicyclic lactone 22. While the deoxygenation of 22 proved to be problematical, the uncyclized variant 25 underwent the Barton process smoothly. These findings guided the related conversion of (-)-11 into 34. Use was also made of ring-closing metathesis to bring about the conversion of (+)-11 into [4.2.0] bicyclic lactone building blocks. In general, all three pathways are efficient and offer the prospect of practical side-chain appendage for the purpose of installing the nine-membered ring of pestalotiopsin A (1).

  DOI：

  10.1021/jo070861r