(1S,3S,4R)-3-benzyloxy-2,2-dimethyl-4-(2-hydroxyethyl)cyclobutan-1-ol | 952101-27-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,3S,4R)-3-benzyloxy-2,2-dimethyl-4-(2-hydroxyethyl)cyclobutan-1-ol
• 英文别名: (1S,3S,4R)-4-(2-hydroxyethyl)-2,2-dimethyl-3-phenylmethoxycyclobutan-1-ol
• CAS: 952101-27-8
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: MNNUJQVZPFRZEE-RDBSUJKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,3S,4R)-3-benzyloxy-2,2-dimethyl-4-(2-hydroxyethyl)cyclobutan-1-ol 在 palladium on activated charcoal 四丙基高钌酸铵 、 4 A molecular sieve 、 氢气 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 49.0h， 生成 (1S,5S,6S)-7,7-dimethyl-6-hydroxy-2-oxabicyclo[3.2.0]heptan-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,3S,4S)-1-(tert-butyldimethylsilyloxy)-3-benzyloxy-2,2-dimethyl-4-(2-hydroxyethyl)cyclobutane 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以96%的产率得到(1S,3S,4R)-3-benzyloxy-2,2-dimethyl-4-(2-hydroxyethyl)cyclobutan-1-ol
  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