(2R)-cyclopentyl glycine ethyl ester | 223473-31-2

• 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: (2R)-cyclopentyl glycine ethyl ester
• 英文别名: Ethyl (R)-2-amino-2-cyclopentylacetate；ethyl (2R)-2-amino-2-cyclopentylacetate
• CAS: 223473-31-2
• 化学式: C₉H₁₇NO₂
• 分子量: 171.239
• InChiKey: QIHMFSRVNXGXQC-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-cyclopentyl glycine ethyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到2-amino-(2R)-cyclopentyl-ethanol
  参考文献：
  名称：

  New Expedient Route to Both Enantiomers of Nonproteinogenic α-Amino Acid Derivatives from the Unsaturated 2-Aza-Bicyclo Moiety

  摘要：

  The influence of the reaction conditions on the catalytic hydrogenation of 2-aza-bicyclo hept-5-ene and oct-5-ene derivatives has been investigated. We found it possible to fully control the extent of allylic vs benzylic C-N hydrogenolysis by simple variations of H-2 pressure and acidity of the reaction medium. The use of the reaction pathways was demonstrated by the selective preparation of four categories of optically active alpha-amino acid derivatives. The strategy was also extended to the synthesis of enantiopure alpha-amino ketones.

  DOI：

  10.1021/jo981838w
• 作为产物：
  描述：

  (1R,3R,4S)-2-<(1S)-phenylethyl>-2-aza-bicyclo<2.2.1>hept-5-ene-3-carboxylic acid ethyl ester 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以96%的产率得到(2R)-cyclopentyl glycine ethyl ester
  参考文献：
  名称：

  New Expedient Route to Both Enantiomers of Nonproteinogenic α-Amino Acid Derivatives from the Unsaturated 2-Aza-Bicyclo Moiety

  摘要：

  The influence of the reaction conditions on the catalytic hydrogenation of 2-aza-bicyclo hept-5-ene and oct-5-ene derivatives has been investigated. We found it possible to fully control the extent of allylic vs benzylic C-N hydrogenolysis by simple variations of H-2 pressure and acidity of the reaction medium. The use of the reaction pathways was demonstrated by the selective preparation of four categories of optically active alpha-amino acid derivatives. The strategy was also extended to the synthesis of enantiopure alpha-amino ketones.

  DOI：

  10.1021/jo981838w

文献信息

• New Expedient Route to Both Enantiomers of Nonproteinogenic α-Amino Acid Derivatives from the Unsaturated 2-Aza-Bicyclo Moiety
  作者：Diego A. Alonso、Sophie K. Bertilsson、Sandra Y. Johnsson、Sofia J. M. Nordin、Mikael J. Södergren、Pher G. Andersson

  DOI：10.1021/jo981838w

  日期：1999.4.1

  The influence of the reaction conditions on the catalytic hydrogenation of 2-aza-bicyclo hept-5-ene and oct-5-ene derivatives has been investigated. We found it possible to fully control the extent of allylic vs benzylic C-N hydrogenolysis by simple variations of H-2 pressure and acidity of the reaction medium. The use of the reaction pathways was demonstrated by the selective preparation of four categories of optically active alpha-amino acid derivatives. The strategy was also extended to the synthesis of enantiopure alpha-amino ketones.