(2S)-azidophenylacetic acid | 29129-67-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-azidophenylacetic acid
• 英文别名: (2S)-2-azido-2-phenylacetic acid
• CAS: 29129-67-7
• 化学式: C₈H₇N₃O₂
• 分子量: 177.162
• InChiKey: XUICXMXDTICQOZ-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  51.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-azidophenylacetic acid 在 氯化亚砜 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 叔丁醇 为溶剂， 反应 26.83h， 生成 (2S,2'S)-2-[4-(1-tert-butoxycarbonylpyrrolidin-2-yl)-(1,2,3)-triazol-1-yl]-2-phenylacetic acid methyl ester
  参考文献：
  名称：

  Triazolopeptides：手性合成和结构异构体的顺/反脯氨酸比例

  摘要：

  由于顺式/反式脯氨酸的异构化在各种生物学过程中都起着至关重要的作用，因此能够修饰顺式/反式Xaa-Pro比率的肽模拟物尤为重要。报道了一种使用[3 + 2]叠氮化物-炔烃环加成作为关键反应步骤的脯氨酸衍生的三唑类肽的实用方法，并分析了其顺式/反式脯氨酰基比率。结构研究表明顺式百分比和构象稳定性对分子内氢键作用的可调节性。

  DOI：

  10.1016/j.tet.2006.07.007
• 作为产物：
  描述：

  左旋苯甘氨酸 在 triflic azide 、 potassium carbonate 、 copper(II) sulfate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 以87%的产率得到(2S)-azidophenylacetic acid
  参考文献：
  名称：

  Improved Solid-Phase Peptide Synthesis Method Utilizing α-Azide-Protected Amino Acids

  摘要：

  [GRAPHICS]Pure alpha -azido acids were prepared using an efficient diazo transfer method followed by buffered workup, These building blocks were used to prepare small peptides on Wang resin by two approaches, Peptides prone to diketopiperazine formation were prepared in good yields by coupling acids to resin bound iminophosphoranes during Fmoc-Wang synthesis, The iminophosphoranes can also be hydrolyzed under neutral conditions to provide unprotected amines ready for further coupling.

  DOI：

  10.1021/ol0155485

文献信息

• Darapsky, Journal fur praktische Chemie (Leipzig 1954), 1919, vol. <2> 99, p. 224
  作者：Darapsky

  DOI：——

  日期：——
• A practical asymmetric synthesis of homochiral α-arylglycines
  作者：Christelle Mellin-Morlière、David J. Aitken、Steven D. Bull、Stephen G. Davies、Henri-Philippe Husson

  DOI：10.1016/s0957-4166(01)00022-2

  日期：2001.2

  Enantioselective reduction of a series of substituted aryl trichloromethyl ketones with the CBS-catecholborane reagent afforded homochiral aryl trichloromethyl carbinols which have been elaborated to give homochiral alpha -arylglycines in high e.e. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Evans, David A.; Britton, Thomas C.; Ellman, Jonathan A., Journal of the American Chemical Society, 1990, vol. 112, # 10, p. 4011 - 4030
  作者：Evans, David A.、Britton, Thomas C.、Ellman, Jonathan A.、Dorow, Roberta L.

  DOI：——

  日期：——
• Electrophilic azide transfer to chiral enolates. A general approach to the asymmetric synthesis of .alpha.-amino acids
  作者：David A. Evans、Thomas C. Britton

  DOI：10.1021/ja00256a069

  日期：1987.10
• Enzymatic and chiral HPLC resolution of α-azido acids and amides
  作者：Christian W Tornøe、Theo Sonke、Ilse Maes、Hans E Schoemaker、Morten Meldal

  DOI：10.1016/s0957-4166(00)00043-4

  日期：2000.3

  For the first time, enzymatic resolution of alpha-azido acid amides has been successfully demonstrated with high yields and enantiomeric excess. In one case dynamic kinetic resolution was achieved leading to more than 50% yield of the enantiomerically pure azido acid. Chiral HPLC was also used to separate racemic alpha-azido acids and the separation process was automated. Two routes to enantiopure alpha-azido acid building blocks for solid-phase peptide synthesis have, therefore, been established. (C) 2000 Elsevier Science Ltd. All rights reserved.