(R)-N-[(S)-1-phenylethyl]-2-(2,6-dioxo-1-piperidinyl)-2-fluoroethanamide | 1130887-86-3

• 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: (R)-N-[(S)-1-phenylethyl]-2-(2,6-dioxo-1-piperidinyl)-2-fluoroethanamide
• 英文别名: (2S)-2-(2,6-dioxopiperidin-1-yl)-2-fluoro-N-[(1S)-1-phenylethyl]acetamide
• CAS: 1130887-86-3
• 化学式: C₁₅H₁₇FN₂O₃
• 分子量: 292.31
• InChiKey: WFQIRSXPEUWTRN-IINYFYTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  戊二酰亚胺 、 (RS)-N-[(S)-1-phenylethyl]-2-fluoro-2-iodoethanamide 在 sodium bis(trimethylsilyl)amide 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-N-[(S)-1-phenylethyl]-2-(2,6-dioxo-1-piperidinyl)-2-fluoroethanamide 、 (R)-N-[(S)-1-phenylethyl]-2-(2,6-dioxo-1-piperidinyl)-2-fluoroethanamide
  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

文献信息

• Synthesis and reactions of α-fluoro-α-amino amides
  作者：Patrick D. Bailey、Andrew N. Boa、Joanne Clayson

  DOI：10.1016/j.tet.2008.11.061

  日期：2009.2

  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.