(2S,3S)-3-azido-2-benzoyloxy-N,N-dimethyl-3-phenylpropanamide | 848477-57-6

• 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,3S)-3-azido-2-benzoyloxy-N,N-dimethyl-3-phenylpropanamide
• CAS: 848477-57-6
• 化学式: C₁₈H₁₈N₄O₃
• 分子量: 338.366
• InChiKey: YWGCKHGPIYANAQ-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  95.37
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-azido-2-benzoyloxy-N,N-dimethyl-3-phenylpropanamide 在 palladium on activated charcoal sodium hydroxide 、 氯化亚砜 、 氢气 作用下， 以 乙醇 、 氯仿 、 乙酸乙酯 为溶剂， 20.0~60.0 ℃ 、101.33 kPa 条件下， 反应 152.0h， 生成 (±)-trans-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid
  参考文献：
  名称：

  Dynamic Ligand Exchange of the Lanthanide Complex Leading to Structural and Functional Transformation:  One-Pot Sequential Catalytic Asymmetric Epoxidation-Regioselective Epoxide-Opening Process

  摘要：

  The characteristic property of the lanthanide complex, which easily undergoes a dynamic ligand exchange and alters its structure and function in situ, is described. After the completion of the catalytic asymmetric epoxidation of various a,beta-unsaturated amides 2 in the presence of the Sm-(S)-BINOL-Ph3As=O (1:1:1) complex 1 (2-10 mol %), the addition of Me3SiN3 directly to the reaction mixture led to smooth epoxide-opening at room temperature, affording the corresponding anti-beta-azido-alpha-hydroxyamide 4 in excellent overall yield (up to 99%) with complete regioselectivity and excellent enantiomeric excess (up to >99%). The key to the success of the sequential process was the in situ generation of the highly reactive samarium azide complex through dynamic ligand exchange. In situ IR spectroscopy and other experiments provided strong evidence that the samariurn azide complex was generated. In addition, the relatively high Lewis basicity of the amide moiety had a key role in the high reactivity of both the epoxidation and the epoxide-opening reactions. Examinations of other nucleophiles such as sulfur or carbon nucleophiles as well as transformations of epoxide-opened products are also described.

  DOI：

  10.1021/ja043770+
• 作为产物：
  描述：

  2-丙烯酰胺,N,N-二甲基-3-苯基-,(2E)- 在 叔丁基过氧化氢 4-二甲氨基吡啶 、 叠氮基三甲基硅烷 、 三苯胂氧化物 、 (R)-1,1'-Bi-2-naphthol 、 samarium(III) isopropoxide 、 三乙胺 作用下， 以 四氢呋喃 、 癸烷 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 (2S,3S)-3-azido-2-benzoyloxy-N,N-dimethyl-3-phenylpropanamide
  参考文献：
  名称：

  Dynamic Ligand Exchange of the Lanthanide Complex Leading to Structural and Functional Transformation:  One-Pot Sequential Catalytic Asymmetric Epoxidation-Regioselective Epoxide-Opening Process

  摘要：

  The characteristic property of the lanthanide complex, which easily undergoes a dynamic ligand exchange and alters its structure and function in situ, is described. After the completion of the catalytic asymmetric epoxidation of various a,beta-unsaturated amides 2 in the presence of the Sm-(S)-BINOL-Ph3As=O (1:1:1) complex 1 (2-10 mol %), the addition of Me3SiN3 directly to the reaction mixture led to smooth epoxide-opening at room temperature, affording the corresponding anti-beta-azido-alpha-hydroxyamide 4 in excellent overall yield (up to 99%) with complete regioselectivity and excellent enantiomeric excess (up to >99%). The key to the success of the sequential process was the in situ generation of the highly reactive samarium azide complex through dynamic ligand exchange. In situ IR spectroscopy and other experiments provided strong evidence that the samariurn azide complex was generated. In addition, the relatively high Lewis basicity of the amide moiety had a key role in the high reactivity of both the epoxidation and the epoxide-opening reactions. Examinations of other nucleophiles such as sulfur or carbon nucleophiles as well as transformations of epoxide-opened products are also described.

  DOI：

  10.1021/ja043770+