(1S,6S,7S)-7-benzyloxy-8,8-dimethyl-2-oxabicyclo[4.2.0]oct-4-en-3-one | 952092-33-0

• 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,6S,7S)-7-benzyloxy-8,8-dimethyl-2-oxabicyclo[4.2.0]oct-4-en-3-one
• 英文别名: (1S,6S,7S)-7-(Benzyloxy)-8,8-dimethyl-2-oxabicyclo[4.2.0]oct-4-EN-3-one；(1S,6S,7S)-8,8-dimethyl-7-phenylmethoxy-2-oxabicyclo[4.2.0]oct-4-en-3-one
• CAS: 952092-33-0
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: ZFGOCAHJOAUTBF-QEJZJMRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,6S,7S)-7-benzyloxy-8,8-dimethyl-2-oxabicyclo[4.2.0]oct-4-en-3-one 在 copper(l) iodide 、 三甲基氯硅烷 、 四甲基乙二胺 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 5.33h， 生成 (1S,4S,5R,6S,7S)-7-benzyloxy-8,8-dimethyl-4-(phenylselanyl)-5-vinyl-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：

  acrylic acid (1S,3S,4R)-3-benzyloxy-2,2-dimethyl-4-vinylcyclobutyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以94%的产率得到(1S,6S,7S)-7-benzyloxy-8,8-dimethyl-2-oxabicyclo[4.2.0]oct-4-en-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

文献信息

• Pestalotiopsin A. Enantioselective Construction of Potential Building Blocks Derived from Antipodal Cyclobutanol Intermediates
  作者：Leo A. Paquette、Gregory D. Parker、Takahiro Tei、Shuzhi Dong

  DOI：10.1021/jo070861r

  日期：2007.9.1

  [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).