2,2,2-trifluoro-N-((S)-1-(4-nitrophenyl)ethyl)acetamide | 1113041-68-1

• 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: 2,2,2-trifluoro-N-((S)-1-(4-nitrophenyl)ethyl)acetamide
• 英文别名: (S)-N-[1-(4-nitrophenyl)ethyl]trifluoroacetamide；(S)-2,2,2-trifluoro-N-(1-(4-nitrophenyl)ethyl)acetamide；2,2,2-trifluoro-N-[(1S)-1-(4-nitrophenyl)ethyl]acetamide
• CAS: 1113041-68-1
• 化学式: C₁₀H₉F₃N₂O₃
• 分子量: 262.188
• InChiKey: SCKNJDFHRITCGN-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoro-N-((S)-1-(4-nitrophenyl)ethyl)acetamide 在 5% Pd(II)/C(eggshell) 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 以99%的产率得到(S)-N-[1-(4-aminophenyl)ethyl]trifluoroacetamide
  参考文献：
  名称：

  Novel Peptoid Building Blocks: Synthesis of Functionalized Aromatic Helix-Inducing Submonomers

  摘要：

  Peptoids, oligo-N-substituted glycines, can fold into well-defined helical secondary structures. The design and synthesis of new peptoid building blocks that are capable of both (a) inducing a helical secondary structure and (b) decorating the helices with chemical functionalities are reported. Peptoid heptamers containing carboxamide, carboxylic acid or thiol functionalities were synthesized, and the resulting peptoids were shown to form stable helices. A thiol-containing peptoid readily formed the homodisulfide. providing a convenient route to prepare peptoid helix homodimers.

  DOI：

  10.1021/ol902660p
• 作为产物：
  描述：

  三氟乙酸乙酯 、 (S)-1-(4-nitrophenyl)ethanamine hydrochloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 120.0h， 以89%的产率得到2,2,2-trifluoro-N-((S)-1-(4-nitrophenyl)ethyl)acetamide
  参考文献：
  名称：

  Novel Peptoid Building Blocks: Synthesis of Functionalized Aromatic Helix-Inducing Submonomers

  摘要：

  Peptoids, oligo-N-substituted glycines, can fold into well-defined helical secondary structures. The design and synthesis of new peptoid building blocks that are capable of both (a) inducing a helical secondary structure and (b) decorating the helices with chemical functionalities are reported. Peptoid heptamers containing carboxamide, carboxylic acid or thiol functionalities were synthesized, and the resulting peptoids were shown to form stable helices. A thiol-containing peptoid readily formed the homodisulfide. providing a convenient route to prepare peptoid helix homodimers.

  DOI：

  10.1021/ol902660p

文献信息

• Synthesis and Characterization of Nitroaromatic Peptoids: Fine Tuning Peptoid Secondary Structure through Monomer Position and Functionality
  作者：Sarah A. Fowler、Rinrada Luechapanichkul、Helen E. Blackwell

  DOI：10.1021/jo8023363

  日期：2009.2.20

  position stabilized the threaded loop structure relative to (Nspe)9. Additional experiments revealed that nitroaromatic side chains can influence peptoid nonamer folding by modulating the strength of key intramolecular hydrogen bonds in the peptoid threaded loop structure. Steric interactions were also implicated for the Ns2ne monomer. Overall, this study provides further evidence that aromatic side-chain

  N-取代的甘氨酸寡聚体或拟肽已成为一类重要的折叠体，用于研究生物分子相互作用和作为治疗剂的潜在用途。然而，设计具有先验明确构象的拟肽仍然是一项艰巨的挑战。需要新的方法来解决这个问题，系统研究单个单体单元在全球 peptoid 折叠过程中的作用代表了一种策略。在这里，我们通过设计、合成和表征含有硝基芳族单体单元的拟肽来报告我们对这种方法的努力。这项工作需要合成一种新的手性胺结构单元（S)-1-(2-硝基苯基)乙胺 (s2ne)，可以使用标准固相类肽合成技术轻松安装到类肽中。我们设计了一系列拟肽九聚体，使我们能够探测这种相对缺电子和空间位阻的 α-手性侧链对拟肽结构的影响，即拟肽螺纹环和螺旋。拟肽的圆二色光谱表明硝基芳香单体对拟肽的二级结构有显着影响。具体来说，螺纹环结构在包含交替的N -( S )-1-苯乙基甘氨酸( N spe ) 和N s2ne 单体的九聚体中被破坏，主要构象是螺旋形的。确实，放置单个(
• Novel Peptoid Building Blocks: Synthesis of Functionalized Aromatic Helix-Inducing Submonomers
  作者：Jiwon Seo、Annelise E. Barron、Ronald N. Zuckermann

  DOI：10.1021/ol902660p

  日期：2010.2.5

  Peptoids, oligo-N-substituted glycines, can fold into well-defined helical secondary structures. The design and synthesis of new peptoid building blocks that are capable of both (a) inducing a helical secondary structure and (b) decorating the helices with chemical functionalities are reported. Peptoid heptamers containing carboxamide, carboxylic acid or thiol functionalities were synthesized, and the resulting peptoids were shown to form stable helices. A thiol-containing peptoid readily formed the homodisulfide. providing a convenient route to prepare peptoid helix homodimers.