(+/-) 3-(dimethylphosphoryl)-4-oxononanoic acid | 1178541-73-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+/-) 3-(dimethylphosphoryl)-4-oxononanoic acid
• CAS: 1178541-73-5
• 化学式: C₁₁H₂₁O₆P
• 分子量: 280.258
• InChiKey: WBNLHAPLBOGHQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  18.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  89.9
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (+/-) 3-(dimethylphosphoryl)-4-oxononanoic acid 在 乙酸酐 、 对甲苯磺酸 、 溶剂黄146 作用下， 反应 3.0h， 以41%的产率得到dimethyl (5-oxo-2-pentyl-4,5-dihydrofuran-3-yl)phosphonate
  参考文献：
  名称：

  Enantioselective Brønsted Acid-Catalyzed N-Acyliminium Cyclization Cascades

  摘要：

  An enantioselective Bronsted acid-catalyzed N-acyliminium cyclization cascade of tryptamines with enol lactones to form architecturally complex heterocycles in high enantiomeric excess has been developed. The reaction is technically simple to perform as well as atom-efficient and may be coupled to a gold(1)-catalyzed cycloisomerization of alkynoic acids whereby the key enol lactone reaction partner is generated in situ. Employing up to 10 mol% bulky chiral phosphoric acid catalysts in boiling toluene allowed the product materials to be generated in good overall yields (63-99%) and high enantioselectivities (72-99% ee). With doubly substituted enol lactones, high diastereo- and enantioselectivities were obtained, thus providing a new example of a dynamic kinetic asymmetric cyclization reaction.

  DOI：

  10.1021/ja9024885
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以922 mg的产率得到(+/-) 3-(dimethylphosphoryl)-4-oxononanoic acid
  参考文献：
  名称：

  Enantioselective Brønsted Acid-Catalyzed N-Acyliminium Cyclization Cascades

  摘要：

  An enantioselective Bronsted acid-catalyzed N-acyliminium cyclization cascade of tryptamines with enol lactones to form architecturally complex heterocycles in high enantiomeric excess has been developed. The reaction is technically simple to perform as well as atom-efficient and may be coupled to a gold(1)-catalyzed cycloisomerization of alkynoic acids whereby the key enol lactone reaction partner is generated in situ. Employing up to 10 mol% bulky chiral phosphoric acid catalysts in boiling toluene allowed the product materials to be generated in good overall yields (63-99%) and high enantioselectivities (72-99% ee). With doubly substituted enol lactones, high diastereo- and enantioselectivities were obtained, thus providing a new example of a dynamic kinetic asymmetric cyclization reaction.

  DOI：

  10.1021/ja9024885