| 1402918-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• CAS: 1402918-16-4
• 化学式: C₁₈H₂₉ClO₅
• 分子量: 360.878
• InChiKey: GJOWZYGMNVXTKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  24.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 吡啶 、 铂(0)-1,3-二乙烯-1,1,3,3-四甲基二硅氧烷 、 硫酸 、 四丁基氟化铵 、 L-Selectride 作用下， 以 四氢呋喃 、 5,5-dimethyl-1,3-cyclohexadiene 、 乙醚 、 乙醇 为溶剂， 反应 5.92h， 生成
  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：

  C₉H₁₆O₃ 在 N-氯代丁二酰亚胺 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 16.33h， 生成
  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