1-(benzylamino)-1-oxoundecan-4-yl acetate | 1233882-47-7

• 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: 1-(benzylamino)-1-oxoundecan-4-yl acetate
• CAS: 1233882-47-7
• 化学式: C₂₀H₃₁NO₃
• 分子量: 333.471
• InChiKey: BWMNDQFWWPKFOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  24.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(benzylamino)-1-oxoundecan-4-yl acetate 在 甲醇 、 Novozym 435 作用下， 以 异丙醚 为溶剂， 反应 24.0h， 以51%的产率得到(R)-1-(benzylamino)-1-oxoundecan-4-yl acetate
  参考文献：
  名称：

  Combination of Novozym 435–Catalyzed Hydrolysis and Mitsunobu Reaction for Production of (R)-γ-Lactones

  摘要：

  Chiral -lactones of both enantiomers were synthesized with more than 90% optical purities. The key step was Novozym 435-catalyzed hydrolysis of racemic N-benzyl-4-acetoxyalkylamides. Additionally, because (R)--lactones are predominant in apricot, mango, peach, passion fruit, and strawberry, synthesis was attempted using only one enantiomer selectively. The (R)-enantimer was synthesized with more than 80% total yield and more than 90% optical purity by a combination of Novozym 435-catalyzed hydrolysis and the Mitsunobu reaction.

  DOI：

  10.1080/00397910903134618
• 作为产物：
  描述：

  乙酸酐 、 N-benzyl-4-hydroxyundecanamide 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 1-(benzylamino)-1-oxoundecan-4-yl acetate
  参考文献：
  名称：

  Combination of Novozym 435–Catalyzed Hydrolysis and Mitsunobu Reaction for Production of (R)-γ-Lactones

  摘要：

  Chiral -lactones of both enantiomers were synthesized with more than 90% optical purities. The key step was Novozym 435-catalyzed hydrolysis of racemic N-benzyl-4-acetoxyalkylamides. Additionally, because (R)--lactones are predominant in apricot, mango, peach, passion fruit, and strawberry, synthesis was attempted using only one enantiomer selectively. The (R)-enantimer was synthesized with more than 80% total yield and more than 90% optical purity by a combination of Novozym 435-catalyzed hydrolysis and the Mitsunobu reaction.

  DOI：

  10.1080/00397910903134618