(RS)-N-benzyl-2-(2,5-dioxo-1-piperidinyl)-2-fluoroethanamide | 216578-86-8

• 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: (RS)-N-benzyl-2-(2,5-dioxo-1-piperidinyl)-2-fluoroethanamide
• 英文别名: N-benzyl-2-(2,6-dioxopiperidin-1-yl)-2-fluoroacetamide
• CAS: 216578-86-8
• 化学式: C₁₄H₁₅FN₂O₃
• 分子量: 278.283
• InChiKey: KNWUNHTYGGRHDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (RS)-N-benzyl-2-(2,5-dioxo-1-piperidinyl)-2-fluoroethanamide 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 N-benzyl-2-fluoro-2-(2-hydroxy-6-oxopiperidin-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
• 作为产物：
  描述：

  在 硫酸 、 sodium hexamethyldisilazane 、 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 (RS)-N-benzyl-2-(2,5-dioxo-1-piperidinyl)-2-fluoroethanamide
  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

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.
• Synthesis of α-heterosubstituted glycine derivatives from dihaloethanamides
  作者：Patrick D. Bailey、S.Richard Baker、Andrew N. Boa、Joanne Clayson、Georgina M. Rosair

  DOI：10.1016/s0040-4039(98)01658-x

  日期：1998.10

  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.