(5S,6S,9R)-6-isopropyl-9-methyl-1,4-diazaspiro[4.5]decan-2-one | 1024627-08-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (5S,6S,9R)-6-isopropyl-9-methyl-1,4-diazaspiro[4.5]decan-2-one
• 英文别名: (5S,6S,9R)-9-methyl-6-propan-2-yl-1,4-diazaspiro[4.5]decan-3-one
• CAS: 1024627-08-4
• 化学式: C₁₂H₂₂N₂O
• 分子量: 210.319
• InChiKey: GNGBDZGKTRLKSQ-SCVCMEIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5S,6S,9R)-6-isopropyl-9-methyl-1,4-diazaspiro[4.5]decan-2-one 、 2-氟-3,5-二硝基苯甲酸 在 草酰氯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以71%的产率得到(5S,6S,9R)-4-(2-fluoro-3,5-dinitrobenzoyl)-6-isopropyl-9-methyl-1,4-diazaspiro[4.5]decan-2-one
  参考文献：
  名称：

  A new chiral derivatizing agent for the HPLC separation of α-amino acids on a standard reverse-phase column

  摘要：

  A new chiral derivatizing agent for alpha-amino acids is described which leads to diastereomers that can be separated by reverse-phase HPLC with direct detection by a diode array detector. The main advantage of the presented procedure is the fact that an excess of the derivatizing reagent can be employed as the product exhibits an absorption maximum at 360 nm, while the reagent has its absorption maximum at 260 nm. Therefore, it is possible to suppress the reagent signal by a detection wavelength of 400 nm leading to an easy and general method for the enantioseparation of a mixture of dl-amino acids and the determination of the enantiomeric purity of alpha-amino acid as exemplified by 16 different alpha-amino acids.

  DOI：

  10.1007/s00726-010-0665-5
• 作为产物：
  描述：

  (-)-薄荷酮 、 甘氨酰胺盐酸盐 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以50%的产率得到(5S,6S,9R)-6-isopropyl-9-methyl-1,4-diazaspiro[4.5]decan-2-one
  参考文献：
  名称：

  A new chiral derivatizing agent for the HPLC separation of α-amino acids on a standard reverse-phase column

  摘要：

  A new chiral derivatizing agent for alpha-amino acids is described which leads to diastereomers that can be separated by reverse-phase HPLC with direct detection by a diode array detector. The main advantage of the presented procedure is the fact that an excess of the derivatizing reagent can be employed as the product exhibits an absorption maximum at 360 nm, while the reagent has its absorption maximum at 260 nm. Therefore, it is possible to suppress the reagent signal by a detection wavelength of 400 nm leading to an easy and general method for the enantioseparation of a mixture of dl-amino acids and the determination of the enantiomeric purity of alpha-amino acid as exemplified by 16 different alpha-amino acids.

  DOI：

  10.1007/s00726-010-0665-5

文献信息

• Preparation of Imidazolidin-4-ones and Their Evaluation as Hydrolytically Cleavable Precursors for the Slow Release of Bioactive Volatile Carbonyl Derivatives
  作者：Alain Trachsel、Barbara Buchs、Guillaume Godin、Aurélien Crochet、Katharina M. Fromm、Andreas Herrmann

  DOI：10.1002/ejoc.201200081

  日期：2012.5

  Imidazolidin-4-ones are suitable in practical applications as hydrolytically cleavable precursors for the controlled release of fragrant aldehydes and ketones. The corresponding profragrances were prepared by treating aliphatic carbonyl compounds with commercially available amino acid amines in the presence of a base to yield mixtures of diastereomers. The two diastereomers isolated from the reaction

  Imidazolidin-4-ones 适用于实际应用中作为可水解裂解的前体，用于控制释放芳香醛和酮。通过在碱存在下用市售氨基酸胺处理脂肪族羰基化合物以产生非对映异构体的混合物来制备相应的前体香料。从甘氨酰胺盐酸盐与 (-)-薄荷酮反应中分离的两种非对映异构体通过柱色谱分离。异构体的绝对立体化学由核磁共振光谱确定，并由 X 射线单晶结构分析证实。在酸性条件下和质子溶剂中，两种非对映异构体缓慢异构化而不释放酮。通过从缓冲水溶液和阳离子表面活性剂乳液中的溶剂萃取以及沉积到棉花表面后的动态顶空分析来研究前体的水解。一般来说，酮类比醛类更容易释放。增加 C-5 处取代基的大小会降低溶液中和棉花表面的水解速度。基于甘氨酰胺的 imidazolidin-4-ones 比相应的 oxazolidin-4-ones 或 oxazolidines 更有效。溶液中的释放速率、前体结构的疏水性（影响沉积）以及这
• A new chiral derivatizing agent for the HPLC separation of α-amino acids on a standard reverse-phase column
  作者：A. F. Kotthaus、H.-J. Altenbach

  DOI：10.1007/s00726-010-0665-5

  日期：2011.2

  A new chiral derivatizing agent for alpha-amino acids is described which leads to diastereomers that can be separated by reverse-phase HPLC with direct detection by a diode array detector. The main advantage of the presented procedure is the fact that an excess of the derivatizing reagent can be employed as the product exhibits an absorption maximum at 360 nm, while the reagent has its absorption maximum at 260 nm. Therefore, it is possible to suppress the reagent signal by a detection wavelength of 400 nm leading to an easy and general method for the enantioseparation of a mixture of dl-amino acids and the determination of the enantiomeric purity of alpha-amino acid as exemplified by 16 different alpha-amino acids.