(2S,3S)-3-Benzyl-oxirane-2-carboxylic acid | 608520-03-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (2S,3S)-3-Benzyl-oxirane-2-carboxylic acid
• 英文别名: (2S,3S)-3-benzyloxirane-2-carboxylic acid
• CAS: 608520-03-2
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: WFWJUTYQYLLJHM-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-Benzyl-oxirane-2-carboxylic acid 在 copper(II) nitrate sodium tetrahydroborate 、 sodium azide 作用下， 以 水 为溶剂， 反应 2.0h， 生成 (2S,3R)-3-氨基-2-羟基-4-苯丁酸
  参考文献：
  名称：

  First One-Pot Copper-Catalyzed Synthesis of α-Hydroxy-β-Amino Acids in Water. A New Protocol for Preparation of Optically Active Norstatines

  摘要：

  alpha-Hydroxy-beta-amino acids were synthesized with excellent yields for the first time in water and by a simple procedure based on a copper catalytic cycle, which included the recovery and reuse of the catalyst and is possible to realize by using only water as reaction medium.

  DOI：

  10.1021/jo034752y
• 作为产物：
  描述：

  4-苯基-2-丁烯醇 在 ruthenium trichloride 、 过碘酸 作用下， 生成 (2S,3S)-3-Benzyl-oxirane-2-carboxylic acid
  参考文献：
  名称：

  First One-Pot Copper-Catalyzed Synthesis of α-Hydroxy-β-Amino Acids in Water. A New Protocol for Preparation of Optically Active Norstatines

  摘要：

  alpha-Hydroxy-beta-amino acids were synthesized with excellent yields for the first time in water and by a simple procedure based on a copper catalytic cycle, which included the recovery and reuse of the catalyst and is possible to realize by using only water as reaction medium.

  DOI：

  10.1021/jo034752y

文献信息

• First One<i>-</i>Pot Copper-Catalyzed Synthesis of α-Hydroxy-β-Amino Acids in Water. A New Protocol for Preparation of Optically Active Norstatines
  作者：Francesco Fringuelli、Ferdinando Pizzo、Mauro Rucci、Luigi Vaccaro

  DOI：10.1021/jo034752y

  日期：2003.9.1

  alpha-Hydroxy-beta-amino acids were synthesized with excellent yields for the first time in water and by a simple procedure based on a copper catalytic cycle, which included the recovery and reuse of the catalyst and is possible to realize by using only water as reaction medium.