Nona-5,8-dien-2-one | 82259-93-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Nona-5,8-dien-2-one
• 英文别名: nona-5,8-dien-2-one
• CAS: 82259-93-6
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: WFHFJLVALSADSA-UHFFFAOYSA-N

物化性质

• 沸点：
  220.0±19.0 °C(Predicted)
• 密度：
  0.848±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Nona-5,8-dien-2-one 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 0.5h， 以62%的产率得到Nona-5,8-dien-2-ol
  参考文献：
  名称：

  Concise Synthetic Approaches for the Laurencia Family: Formal Total Syntheses of (±)-Laurefucin and (±)-E- and (±)-Z-Pinnatifidenyne

  摘要：

  Herein is presented a cohesive strategy to rapidly fashion diverse members of the lauroxocane family of natural products, leading to the shortest syntheses of any member to date. These efforts include racemic formal total syntheses of laurefucin and E- and Z-pinnatifidenyne as well as a facile preparation of the oxocene core of 3E-dehydrobromolaurefucin. The key elements of the design are novel diastereoselective ring-expanding bromoetherifications of tetrahydrofurans triggered by a unique bromonium source (BDSB, Et2SBr center dot SbBrCl5) and strategically positioned nucleophilic traps, where altering the identity and position of these traps affords diverse functionality on the eight-membered ring backbone. Its biogenetic relevance is also discussed in light of the range of substrates that successfully undergo this key rearrangement.

  DOI：

  10.1021/ja3076988
• 作为产物：
  描述：

  1,5-己二烯醇 、 2-甲氧基丙烯 在 mercury(II) diacetate 作用下， 反应 24.0h， 生成 Nona-5,8-dien-2-one
  参考文献：
  名称：

  Concise Synthetic Approaches for the Laurencia Family: Formal Total Syntheses of (±)-Laurefucin and (±)-E- and (±)-Z-Pinnatifidenyne

  摘要：

  Herein is presented a cohesive strategy to rapidly fashion diverse members of the lauroxocane family of natural products, leading to the shortest syntheses of any member to date. These efforts include racemic formal total syntheses of laurefucin and E- and Z-pinnatifidenyne as well as a facile preparation of the oxocene core of 3E-dehydrobromolaurefucin. The key elements of the design are novel diastereoselective ring-expanding bromoetherifications of tetrahydrofurans triggered by a unique bromonium source (BDSB, Et2SBr center dot SbBrCl5) and strategically positioned nucleophilic traps, where altering the identity and position of these traps affords diverse functionality on the eight-membered ring backbone. Its biogenetic relevance is also discussed in light of the range of substrates that successfully undergo this key rearrangement.

  DOI：

  10.1021/ja3076988

文献信息

• Concise Synthetic Approaches for the Laurencia Family: Formal Total Syntheses of (±)-Laurefucin and (±)-<i>E</i>- and (±)-<i>Z</i>-Pinnatifidenyne
  作者：Scott A. Snyder、Alexandria P. Brucks、Daniel S. Treitler、Ioana Moga

  DOI：10.1021/ja3076988

  日期：2012.10.24

  Herein is presented a cohesive strategy to rapidly fashion diverse members of the lauroxocane family of natural products, leading to the shortest syntheses of any member to date. These efforts include racemic formal total syntheses of laurefucin and E- and Z-pinnatifidenyne as well as a facile preparation of the oxocene core of 3E-dehydrobromolaurefucin. The key elements of the design are novel diastereoselective ring-expanding bromoetherifications of tetrahydrofurans triggered by a unique bromonium source (BDSB, Et2SBr center dot SbBrCl5) and strategically positioned nucleophilic traps, where altering the identity and position of these traps affords diverse functionality on the eight-membered ring backbone. Its biogenetic relevance is also discussed in light of the range of substrates that successfully undergo this key rearrangement.