(+/-)-3c_F-azido-2r_F-hydroxy-3cat_F-phenyl-propionic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (+/-)-3c_F-azido-2r_F-hydroxy-3cat_F-phenyl-propionic acid
• 英文别名: (+/-)-3c_F-Azido-2r_F-hydroxy-3cat_F-phenyl-propionsaeure；(2RS:3RS)-3-Azido-2-hydroxy-3-phenyl-propionsaeure；(2S,3S)-3-azido-2-hydroxy-3-phenylpropanoic acid
• 化学式: C₉H₉N₃O₃
• 分子量: 207.189
• InChiKey: VRFDFWYTHFTWQA-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  71.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-3c_F-azido-2r_F-hydroxy-3cat_F-phenyl-propionic acid 以 乙醚 为溶剂， 25.0~110.0 ℃ 、66.66 Pa 条件下， 反应 24.5h， 生成 rac Methyl (2R^*,3S^*)-3-phenyl-1H-aziridine-2-carboxylate
  参考文献：
  名称：

  Synthesis of all four homochiral stereoisomers of methyl 3-phenyl-1h-aziridine-2-car☐ylate

  摘要：

  DOI：

  10.1016/s0040-4020(01)82040-8
• 作为产物：
  描述：

  sodium (E)-3-phenylglycidate 在 sodium azide 作用下， 以 水 为溶剂， 反应 24.0h， 生成 (+/-)-3c_F-azido-2r_F-hydroxy-3cat_F-phenyl-propionic acid
  参考文献：
  名称：

  Synthesis of all four homochiral stereoisomers of methyl 3-phenyl-1h-aziridine-2-car☐ylate

  摘要：

  DOI：

  10.1016/s0040-4020(01)82040-8

文献信息

• Rao; Venkataraman, Journal of the Indian Chemical Society, 1938, vol. 15, p. 194,199
  作者：Rao、Venkataraman

  DOI：——

  日期：——
• 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.
• Azidolysis of α,β-Epoxycarboxylic Acids. A Water-Promoted Process Efficiently Catalyzed by Indium Trichloride at pH 4.0
  作者：Francesco Fringuelli、Ferdinando Pizzo、Luigi Vaccaro

  DOI：10.1021/jo015564f

  日期：2001.5.1

  The catalytic efficiency of InCl3, Yb(OTf)(3), and Sc(OTf)(3) in the azidolysis of alpha,beta -epoxycarboxylic acids has been studied in water and in organic solvents, for comparison using NaN3 and Me3SiN3 as the source of the azido group. In water, the catalytic effectiveness of these metal salts strongly depends on the pH of the aqueous medium and on the type of Lewis acid catalyst. In water their catalytic activity is mostly due to the corresponding aqua ion species, the concentration of which becomes significant when the pH of the aqueous medium is below the corresponding pK(1,1) hydrolysis constant. The process is more efficient in water than in organic solvents. At pH 4.0, InCl3 is a far better catalyst than Yb(OTf)(3) or Sc(OTf)(3) and allows the highly regio- and diasteroselective preparation of beta -azido-alpha -hydroxycarboxylic acids, which can be isolated in pure form in very high yields.
• Fringuelli, Francesco; Pizzo, Ferdinando; Vaccaro, Luigi, Synlett, 2000, # 3, p. 311 - 314
  作者：Fringuelli, Francesco、Pizzo, Ferdinando、Vaccaro, Luigi

  DOI：——

  日期：——
• Synthesis of all four homochiral stereoisomers of methyl 3-phenyl-1h-aziridine-2-car☐ylate
  作者：Lambertus Thijs、Jos J.M. orskamp、A.W.M. Adriaan、P.W. Mariëlle、eenstra Rolf W.、Johan Legters、Binne Zwanenburg

  DOI：10.1016/s0040-4020(01)82040-8

  日期：1990.1