(2S)-2-[(5,5-dimethyl-2-oxo-1,3,2lambda5-dioxaphosphinan-2-yl)amino]-3-phenylpropanenitrile | 1236163-13-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S)-2-[(5,5-dimethyl-2-oxo-1,3,2lambda5-dioxaphosphinan-2-yl)amino]-3-phenylpropanenitrile
• 英文别名: (2S)-2-[(5,5-dimethyl-2-oxo-1,3,2λ5-dioxaphosphinan-2-yl)amino]-3-phenylpropanenitrile
• CAS: 1236163-13-5
• 化学式: C₁₄H₁₉N₂O₃P
• 分子量: 294.29
• InChiKey: NODYKEDDEHHTPS-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  、 二乙基氰化铝 在 左旋苯甘氨酸 、 异丙醇 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以92%的产率得到(2S)-2-[(5,5-dimethyl-2-oxo-1,3,2lambda5-dioxaphosphinan-2-yl)amino]-3-phenylpropanenitrile
  参考文献：
  名称：

  Asymmetric Catalytic N-Phosphonyl Imine Chemistry: The Use of Primary Free Amino Acids and Et₂AlCN for Asymmetric Catalytic Strecker Reaction

  摘要：

  The new asymmetric catalytic Strecker reaction of achiral N-phosphonyl imines has been established. Excellent enantioselectivity (95.2-99.7% ee) and yields (89-97%) have been achieved by using primary free natural amino acids as catalysts and Et2AlCN as nucleophile. This work also presents the novel use of nonvolatile and inexpensive Et2AlCN in asymmetric catalysis. The N-phosphonyl protecting group enabled simple product purification to be achieved simply by washing the crude products with hexane, which is defined as the GAP chemistry (GAP: Group-Assistant-Purification).(15) It can also be readily cleaved and recycled under mild condition to give a quantitative recovery of N,N'-bis(naphthalen-1-ylmethyl)ethane-1,2-diamine. A new mechanism was proposed for this reaction and was supported by experimental observations.

  DOI：

  10.1021/jo100865q

文献信息

• Asymmetric Catalytic <i>N</i>-Phosphonyl Imine Chemistry: The Use of Primary Free Amino Acids and Et₂AlCN for Asymmetric Catalytic Strecker Reaction
  作者：Parminder Kaur、Suresh Pindi、Walter Wever、Trideep Rajale、Guigen Li

  DOI：10.1021/jo100865q

  日期：2010.8.6

  The new asymmetric catalytic Strecker reaction of achiral N-phosphonyl imines has been established. Excellent enantioselectivity (95.2-99.7% ee) and yields (89-97%) have been achieved by using primary free natural amino acids as catalysts and Et2AlCN as nucleophile. This work also presents the novel use of nonvolatile and inexpensive Et2AlCN in asymmetric catalysis. The N-phosphonyl protecting group enabled simple product purification to be achieved simply by washing the crude products with hexane, which is defined as the GAP chemistry (GAP: Group-Assistant-Purification).(15) It can also be readily cleaved and recycled under mild condition to give a quantitative recovery of N,N'-bis(naphthalen-1-ylmethyl)ethane-1,2-diamine. A new mechanism was proposed for this reaction and was supported by experimental observations.