(S)-N-(4-Nitrobenzyloxycarbonyl)-β-phenyl-β-alanine | 137050-87-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (S)-N-(4-Nitrobenzyloxycarbonyl)-β-phenyl-β-alanine
• CAS: 137050-87-4
• 化学式: C₁₇H₁₆N₂O₆
• 分子量: 344.324
• InChiKey: BUKJBFCAJMFAMA-HNNXBMFYSA-N

物化性质

• 沸点：
  589.4±50.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  118.77
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-N-(4-Nitrobenzyloxycarbonyl)-β-phenyl-β-alanine 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 18.0h， 以74%的产率得到(S)-3-氨基-3-苯基丙酸盐酸盐
  参考文献：
  名称：

  Carbohydrates as chiral templates: diastereoselective synthesis of N-glycosyl-N-homoallylamines and .beta.-amino acids from imines

  摘要：

  Complexing properties and chirality of carbohydrates were utilized in diastereoselective reactions of O-pivaloylated N-galactosylimines with allylsilanes and -stannanes. With allyltrimethylsilane in the presence of SnCl4, imines 2 of aromatic and heteroaromatic aldehydes were converted to homoallylamines 3, giving ratios of diastereomers higher than 7:1. No addition products derived from alpha-anomeric aromatic imines were formed. Aliphatic homoallylamines 3 were synthesized by using allyltributylstannane in the presence of SnCl4. Both alpha- and beta-anomeric aliphatic imines reacted with the allylstannane. They gave the same ratio of diastereomers and showed the same sense of asymmetric induction.

  DOI：

  10.1021/jo00020a033
• 作为产物：
  描述：

  (S)-N-(4-Nitrobenzyloxycarbonyl)-1-phenyl-3-butenylamine 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 3.5h， 以87%的产率得到(S)-N-(4-Nitrobenzyloxycarbonyl)-β-phenyl-β-alanine
  参考文献：
  名称：

  Carbohydrates as chiral templates: diastereoselective synthesis of N-glycosyl-N-homoallylamines and .beta.-amino acids from imines

  摘要：

  Complexing properties and chirality of carbohydrates were utilized in diastereoselective reactions of O-pivaloylated N-galactosylimines with allylsilanes and -stannanes. With allyltrimethylsilane in the presence of SnCl4, imines 2 of aromatic and heteroaromatic aldehydes were converted to homoallylamines 3, giving ratios of diastereomers higher than 7:1. No addition products derived from alpha-anomeric aromatic imines were formed. Aliphatic homoallylamines 3 were synthesized by using allyltributylstannane in the presence of SnCl4. Both alpha- and beta-anomeric aliphatic imines reacted with the allylstannane. They gave the same ratio of diastereomers and showed the same sense of asymmetric induction.

  DOI：

  10.1021/jo00020a033