(S) 3-isopropyl-morpholin-2-one | 197713-95-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S) 3-isopropyl-morpholin-2-one
• 英文别名: (3S)-3-propan-2-ylmorpholin-2-one
• CAS: 197713-95-4
• 化学式: C₇H₁₃NO₂
• 分子量: 143.186
• InChiKey: QPKDEYCQTZSMJI-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl (R)-4-methyl-2-(trifluoromethylsulfonyloxy)pentanoate 、 (S) 3-isopropyl-morpholin-2-one 在 lutidine 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 96.0h， 以35%的产率得到(S)-2-((S)-3-Isopropyl-2-oxo-morpholin-4-yl)-3-methyl-butyric acid benzyl ester
  参考文献：
  名称：

  Synthesis of a sterically congested α,α′-iminodiacid

  摘要：

  The synthesis of iminodiacid 2, a derivative of valine, was found to be difficult at the point of attempting to functionalize the imino-nitrogen to form a tertiary amine. Nonetheless, a route was discovered starting from alpha-hydroxyisovaleric acid, ethanolamine and maleimide. After esterification, the alpha-triflate of alpha-hydroxyisovaleric acid was formed and used to sequentially alkylate the amino group of ethanolamine. Steric hindrance was reduced by tethering two of the amine substituents into lactone ring. This was followed by maleimide substitution of the hydroxyl group under Mitsunobu conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)01065-x
• 作为产物：
  描述：

  benzyl (R)-4-methyl-2-(trifluoromethylsulfonyloxy)pentanoate 在 对甲苯磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 (S) 3-isopropyl-morpholin-2-one
  参考文献：
  名称：

  Natural α-amino acid based synthesis of morpholin-2-ones, prospective monomers for new-generation polymeric lipofectants

  摘要：

  DOI：

  10.1016/j.mencom.2024.01.009

文献信息

• Synthesis of a sterically congested α,α′-iminodiacid
  作者：Michael A Walker

  DOI：10.1016/s0040-4020(97)01065-x

  日期：1997.10

  The synthesis of iminodiacid 2, a derivative of valine, was found to be difficult at the point of attempting to functionalize the imino-nitrogen to form a tertiary amine. Nonetheless, a route was discovered starting from alpha-hydroxyisovaleric acid, ethanolamine and maleimide. After esterification, the alpha-triflate of alpha-hydroxyisovaleric acid was formed and used to sequentially alkylate the amino group of ethanolamine. Steric hindrance was reduced by tethering two of the amine substituents into lactone ring. This was followed by maleimide substitution of the hydroxyl group under Mitsunobu conditions. (C) 1997 Elsevier Science Ltd.
• Natural α-amino acid based synthesis of morpholin-2-ones, prospective monomers for new-generation polymeric lipofectants
  作者：Evgeny D. Shaputkin、Ilya E. Nifant'ev、Pavel V. Ivchenko

  DOI：10.1016/j.mencom.2024.01.009

  日期：2024.1