(2S)-tert-Butyl 4-oxo-2-amino>nonanoate | 152381-78-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2S)-tert-Butyl 4-oxo-2-amino>nonanoate
• 英文别名: tert-butyl (2S)-5-oxo-2-[(9-phenylfluoren-9-yl)amino]nonanoate
• CAS: 152381-78-7
• 化学式: C₃₂H₃₇NO₃
• 分子量: 483.651
• InChiKey: BKYCUJBIBQOKFJ-LJAQVGFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-tert-Butyl 4-oxo-2-amino>nonanoate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 24.0h， 以87%的产率得到(2S,5S)-5-Butylproline tert-butyl ester
  参考文献：
  名称：

  Synthesis of enantiopure .delta.-oxo .alpha.-amino esters and prolines via acylation of N-(phenylfluorenyl)glutamate enolates

  摘要：

  Acylation of the lithium gamma-enolate of alpha-tert-butyl gamma-methyl N-[9-(9-phenylfluorenyl)]glutamate (1) with different acid chlorides provides beta-keto esters 2. Selective gamma-ester hydrolysis and decarboxylation furnishes good yields of enantiomerically pure delta-oxo alpha-amino esters 3 possessing primary, secondary, and tertiary alkyl, as well as aromatic delta-substituents. Acylation of 1 with methyl oxalyl chloride is followed by condensation of the ketone and amine of 2 to give N-(PhF1)-DELTA2-pyrroline triester 4 in 75% yield. Palladium-catalyzed hydrogenation of (2S)-tert-butyl 4-oxo-2-(N-(PhFl)amino)nonanoate (3f) yields >99.5% enantiopure (2S,5S)-5-butylproline tert-butyl ester (5), an intermediate in the synthesis of 2,5-dialkylpyrrolidine alkaloids.

  DOI：

  10.1021/jo00075a046
• 作为产物：
  描述：

  (S)-2-Pentanoyl-4-(9-phenyl-9H-fluoren-9-ylamino)-pentanedioic acid 5-tert-butyl ester 1-methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (2S)-tert-Butyl 4-oxo-2-amino>nonanoate
  参考文献：
  名称：

  Synthesis of enantiopure .delta.-oxo .alpha.-amino esters and prolines via acylation of N-(phenylfluorenyl)glutamate enolates

  摘要：

  Acylation of the lithium gamma-enolate of alpha-tert-butyl gamma-methyl N-[9-(9-phenylfluorenyl)]glutamate (1) with different acid chlorides provides beta-keto esters 2. Selective gamma-ester hydrolysis and decarboxylation furnishes good yields of enantiomerically pure delta-oxo alpha-amino esters 3 possessing primary, secondary, and tertiary alkyl, as well as aromatic delta-substituents. Acylation of 1 with methyl oxalyl chloride is followed by condensation of the ketone and amine of 2 to give N-(PhF1)-DELTA2-pyrroline triester 4 in 75% yield. Palladium-catalyzed hydrogenation of (2S)-tert-butyl 4-oxo-2-(N-(PhFl)amino)nonanoate (3f) yields >99.5% enantiopure (2S,5S)-5-butylproline tert-butyl ester (5), an intermediate in the synthesis of 2,5-dialkylpyrrolidine alkaloids.

  DOI：

  10.1021/jo00075a046

文献信息

• Synthesis of enantiopure .delta.-oxo .alpha.-amino esters and prolines via acylation of N-(phenylfluorenyl)glutamate enolates
  作者：Houda H. Ibrahim、William D. Lubell

  DOI：10.1021/jo00075a046

  日期：1993.11

  Acylation of the lithium gamma-enolate of alpha-tert-butyl gamma-methyl N-[9-(9-phenylfluorenyl)]glutamate (1) with different acid chlorides provides beta-keto esters 2. Selective gamma-ester hydrolysis and decarboxylation furnishes good yields of enantiomerically pure delta-oxo alpha-amino esters 3 possessing primary, secondary, and tertiary alkyl, as well as aromatic delta-substituents. Acylation of 1 with methyl oxalyl chloride is followed by condensation of the ketone and amine of 2 to give N-(PhF1)-DELTA2-pyrroline triester 4 in 75% yield. Palladium-catalyzed hydrogenation of (2S)-tert-butyl 4-oxo-2-(N-(PhFl)amino)nonanoate (3f) yields >99.5% enantiopure (2S,5S)-5-butylproline tert-butyl ester (5), an intermediate in the synthesis of 2,5-dialkylpyrrolidine alkaloids.