N-Benzyl-2-fluoro-2-(2-hydroxy-5-oxo-pyrrolidin-1-yl)-acetamide | 216578-90-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-Benzyl-2-fluoro-2-(2-hydroxy-5-oxo-pyrrolidin-1-yl)-acetamide
• 英文别名: N-benzyl-2-fluoro-2-(2-hydroxy-5-oxo-pyrrolidin-1-yl)acetamide；N-benzyl-2-fluoro-2-(2-hydroxy-5-oxopyrrolidin-1-yl)acetamide
• CAS: 216578-90-4
• 化学式: C₁₃H₁₅FN₂O₃
• 分子量: 266.272
• InChiKey: DJASHODFUHKLIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-乙二硫醇 、 N-Benzyl-2-fluoro-2-(2-hydroxy-5-oxo-pyrrolidin-1-yl)-acetamide 在 三氟化硼乙醚 作用下， 以 氯仿 为溶剂， 以56%的产率得到(4R,8aR)-3-Oxo-hexahydro-5,8-dithia-3a-aza-azulene-4-carboxylic acid benzylamide
  参考文献：
  名称：

  Synthesis of α-heterosubstituted glycine derivatives from dihaloethanamides

  摘要：

  A range of protected a-heterosubstituted analogues of glycine were synthesised from starting materials of the type CHFX-CONHR [X = Cl, Br, I; R = CH2Ph, (S)-CHMePh]; the final products included derivatives of glycine possessing N, O, F or S in the alpha-position, and the first example of a free alpha-fluoro-alpha-amino acid (alpha-fluorobetaine) whose structure was confirmed by X-ray crystal structure determination. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01658-x
• 作为产物：
  描述：

  (RS)-N-benzyl-2-(2,5-dioxo-1-pyrrolidinyl)-2-fluoroethanamide 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 7.5h， 生成 N-Benzyl-2-fluoro-2-(2-hydroxy-5-oxo-pyrrolidin-1-yl)-acetamide
  参考文献：
  名称：

  Synthesis and reactions of α-fluoro-α-amino amides

  摘要：

  N-((S)-1-Phenylethyl)halofluoroethanamides have been investigated as precursors to N-protected alpha-fluoro-alpha-amino amides by nucleophilic displacement of halide with nitrogen nucleophiles such as potassium phthalimide, sodium succinimide, sodium glutarimide, trimethylamine and sodium azide. With single diastereoisomers; of the iodofluoroethanamide, clean inversion of configuration occurs at room temperature, but subsequent epimerisation may occur as a result of the liberated iodide. The alpha-fluoro-alpha-amino amides made underwent a wide variety of reactions depending on conditions, but in many cases the carbon-fluorine bond was compromised. However, reacting trimethylamine and N-((S)-1-phenylethyl)iodofluoroethanamide gave the corresponding alpha-fluorobetaine amide, and subsequent acidic hydrolysis led to alpha-fluorobetaine as the first example of an 'unprotected' alpha-fluoroamino acid. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.061