(+)-(1S,5S,7R)-7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]octan-2-one | 180682-04-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (+)-(1S,5S,7R)-7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]octan-2-one
• 英文别名: (1S,5S,7R)-7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]octan-2-one
• CAS: 180682-04-6
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: NHWBENOPBPKELF-HLTSFMKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 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,5S,7R)-7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]octan-2-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以75%的产率得到(+)-2-hydroxy-exo-brevicomin
  参考文献：
  名称：

  Organometallic Enantiomeric Scaffolding. A Molybdenum-Mediated Intramolecular Nucleophilic Ketalization−Demetalation Cascade. Total Synthesis of (+)-(1R,2S,5S,7R)-2-Hydroxy-exo-brevicomin

  摘要：

  TpMO(CO)(2)(5-OXO-eta(3)-pyranyl) scaffolds bearing an internal alkoxide undergo a novel intramolecular nucleophilic ketalization reaction. The anionic intermediate is easily demetalated, rapidly providing the 6,8-dioxabicyclo[3.2.1]oct-3-en-2-one framework in moderate to good yields with high enantiopurity. An enantiocontrolled total synthesis of (+)-(1R,2S,5S,7R)-2-hydroxy-exo-brevicomin was accomplished utilizing the reaction sequence.

  DOI：

  10.1021/ol901523g
• 作为产物：
  描述：

  (-)-(1S,5S,7R)-7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]oct-3-en-2-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以80%的产率得到(+)-(1S,5S,7R)-7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]octan-2-one
  参考文献：
  名称：

  Organometallic Enantiomeric Scaffolding. A Molybdenum-Mediated Intramolecular Nucleophilic Ketalization−Demetalation Cascade. Total Synthesis of (+)-(1R,2S,5S,7R)-2-Hydroxy-exo-brevicomin

  摘要：

  TpMO(CO)(2)(5-OXO-eta(3)-pyranyl) scaffolds bearing an internal alkoxide undergo a novel intramolecular nucleophilic ketalization reaction. The anionic intermediate is easily demetalated, rapidly providing the 6,8-dioxabicyclo[3.2.1]oct-3-en-2-one framework in moderate to good yields with high enantiopurity. An enantiocontrolled total synthesis of (+)-(1R,2S,5S,7R)-2-hydroxy-exo-brevicomin was accomplished utilizing the reaction sequence.

  DOI：

  10.1021/ol901523g

文献信息

• Organometallic Enantiomeric Scaffolding. A Molybdenum-Mediated Intramolecular Nucleophilic Ketalization−Demetalation Cascade. Total Synthesis of (+)-(1<i>R</i>,2<i>S</i>,5<i>S</i>,7<i>R</i>)-2-Hydroxy-<i>exo</i>-brevicomin
  作者：Bo Cheng、Lanny S. Liebeskind

  DOI：10.1021/ol901523g

  日期：2009.8.20

  TpMO(CO)(2)(5-OXO-eta(3)-pyranyl) scaffolds bearing an internal alkoxide undergo a novel intramolecular nucleophilic ketalization reaction. The anionic intermediate is easily demetalated, rapidly providing the 6,8-dioxabicyclo[3.2.1]oct-3-en-2-one framework in moderate to good yields with high enantiopurity. An enantiocontrolled total synthesis of (+)-(1R,2S,5S,7R)-2-hydroxy-exo-brevicomin was accomplished utilizing the reaction sequence.