(RS)-N-benzyl-2-chloro-2-fluoroethanamide | 216578-83-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (RS)-N-benzyl-2-chloro-2-fluoroethanamide
• 英文别名: N-benzyl-2-chloro-2-fluoroacetamide
• CAS: 216578-83-5
• 化学式: C₉H₉ClFNO
• 分子量: 201.628
• InChiKey: UDTJJYOJNBIZJM-UHFFFAOYSA-N

物化性质

• 熔点：
  56.2-56.7 °C(Solv: hexane (110-54-3); ethyl ether (60-29-7))
• 沸点：
  348.1±42.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (RS)-N-benzyl-2-chloro-2-fluoroethanamide 在 sodium hydride 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 (RS)-N-benzyl-2-(2,5-dioxo-1-pyrrolidinyl)-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
• 作为产物：
  描述：

  在 硫酸 作用下， 生成 (RS)-N-benzyl-2-chloro-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 Reactivity of 1-Substituted 2-Fluoro- and 2,2-Difluoroaziridines
  作者：Guido Verniest、Filip Colpaert、Eva Van Hende、Norbert De Kimpe

  DOI：10.1021/jo071253e

  日期：2007.10.1

  A straightforward synthesis toward 2-fluorinated aziridines was developed via ring closure of β-fluorinated β-chloroamines, which were obtained via reduction of the corresponding α-fluorinated amides by borane. When 1-benzyl-2-fluoroaziridine was treated with methanol, reaction occurred at the 2-position, giving rise to N-benzyl-2,2-dimethoxyethylamine, while in the case of 1-benzyl-2,2-difluoroaziridine

  通过β-氟化β-氯胺的闭环开发了一种直接合成2-氟氮丙啶的方法，该方法是通过用硼烷还原相应的α-氟代酰胺而获得的。当1-苄基-2-氟氮丙啶用甲醇处理时，在2-位发生反应，生成N-苄基-2,2-二甲氧基乙胺，而在1-苄基-2,2-二氟氮丙啶的情况下3 -位被攻击，产生N-苄基-2-甲氧基乙酰胺。这些反应表明单氟-和二氟氮丙啶的反应活性不同。
• 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.