methyl 2-{[(1S)-2-amino-2-oxo-1-phenylethyl]amino}cyclohex-1-ene-1-carboxylate | 679789-06-1

• 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: methyl 2-{[(1S)-2-amino-2-oxo-1-phenylethyl]amino}cyclohex-1-ene-1-carboxylate
• 英文别名: methyl 2-[[(1S)-2-amino-2-oxo-1-phenylethyl]amino]cyclohexene-1-carboxylate
• CAS: 679789-06-1
• 化学式: C₁₆H₂₀N₂O₃
• 分子量: 288.346
• InChiKey: SAJKKOIXJXWJNW-AWEZNQCLSA-N

物化性质

• 沸点：
  490.7±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-{[(1S)-2-amino-2-oxo-1-phenylethyl]amino}cyclohex-1-ene-1-carboxylate 在 platinum(IV) oxide 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以94%的产率得到methyl (1S,2R)-2-{[(1S)-2-amino-2-oxo-1-phenylethyl]amino}cyclohexanecarboxylate
  参考文献：
  名称：

  Highly Diastereoselective Heterogeneously Catalyzed Hydrogenation of Enamines for the Synthesis of Chiral β-Amino Acid Derivatives

  摘要：

  Pure (Z)-enamines readily prepared from beta-ketoesters and amides using (S)-phenylglycine amide were hydrogenated with very high diastereoselectivities (up to 200:1) using heterogeneous catalysis. Hydrogenolytic cleavage of the (S)-phenylglycine amide afforded the corresponding chiral beta-aminoesters and amides. The high geometrical purity of the (Z)-enamine and a simple activation procedure for the PtO2 catalyst are essential in achieving high selectivity.

  DOI：

  10.1021/ja038812t
• 作为产物：
  描述：

  L-苯甘氨酰胺 、 2-氧环己烷羧酸甲酯 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以87%的产率得到methyl 2-{[(1S)-2-amino-2-oxo-1-phenylethyl]amino}cyclohex-1-ene-1-carboxylate
  参考文献：
  名称：

  Highly Diastereoselective Heterogeneously Catalyzed Hydrogenation of Enamines for the Synthesis of Chiral β-Amino Acid Derivatives

  摘要：

  Pure (Z)-enamines readily prepared from beta-ketoesters and amides using (S)-phenylglycine amide were hydrogenated with very high diastereoselectivities (up to 200:1) using heterogeneous catalysis. Hydrogenolytic cleavage of the (S)-phenylglycine amide afforded the corresponding chiral beta-aminoesters and amides. The high geometrical purity of the (Z)-enamine and a simple activation procedure for the PtO2 catalyst are essential in achieving high selectivity.

  DOI：

  10.1021/ja038812t

文献信息

• Highly Diastereoselective Heterogeneously Catalyzed Hydrogenation of Enamines for the Synthesis of Chiral β-Amino Acid Derivatives
  作者：Norihiro Ikemoto、David M. Tellers、Spencer D. Dreher、Jinchu Liu、Angie Huang、Nelo R. Rivera、Eugenia Njolito、Yi Hsiao、J. Christopher McWilliams、J. Michael Williams、Joseph D. Armstrong、Yongkui Sun、David J. Mathre、Edward J. J. Grabowski、Richard D. Tillyer

  DOI：10.1021/ja038812t

  日期：2004.3.1

  Pure (Z)-enamines readily prepared from beta-ketoesters and amides using (S)-phenylglycine amide were hydrogenated with very high diastereoselectivities (up to 200:1) using heterogeneous catalysis. Hydrogenolytic cleavage of the (S)-phenylglycine amide afforded the corresponding chiral beta-aminoesters and amides. The high geometrical purity of the (Z)-enamine and a simple activation procedure for the PtO2 catalyst are essential in achieving high selectivity.