N^α-trifluoroethyl (L)-phenylalanine methyl ester | 950856-19-6

• 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: N^α-trifluoroethyl (L)-phenylalanine methyl ester
• 英文别名: methyl (2,2,2-trifluoroethyl)-L-phenylalaninate；methyl (2S)-3-phenyl-2-(2,2,2-trifluoroethylamino)propanoate
• CAS: 950856-19-6
• 化学式: C₁₂H₁₄F₃NO₂
• 分子量: 261.244
• InChiKey: KJTPNOFOGVPCJR-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N^α-trifluoroethyl (L)-phenylalanine methyl ester 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以93.6%的产率得到
  参考文献：
  名称：

  The first example of linear peptides containing a N-trifluoroethylated backbone amide linkage and the surprising solution dynamics observed by 19F NMR

  摘要：

  The alpha-amino group Of (L)phenylalanine methyl ester was trifluoroethylated using (2,2,2-trifluoroethyl)phenyliodonium N,N-bis(trifluoromethylsulfonyl)imide. A dipeptide Gly(L)Phe containing a trifluoroethylated peptide bond was synthesized by removing the alpha-amino proton of N-alpha-trifluoroethyl (L)phenylalanine methyl ester followed by coupling with N-alpha-phthaloyl glycine acid fluoride. The dipeptide was further coupled with (L)leucine methyl ester under conventional carboxyl activation conditions to provide two diastereomers of the tripeptide Gly(D,L)Phe(L)Leu. The solution dynamic behavior of the tripeptide was investigated as a function of solvents, by NOESY and variable temperature (VT) F-19 NMR experiments. (c) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2007.04.005
• 作为产物：
  描述：

  1,1,1-trifluoro-2-iodoethane;1,1,1-trifluoro-N-phenyl-N-(trifluoromethylsulfonyl)methanesulfonamide 、 L-苯丙氨酸甲酯 在 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 N^α-trifluoroethyl (L)-phenylalanine methyl ester
  参考文献：
  名称：

  Construction of N-1H,1H-perfluoroalkylated peptide bonds

  摘要：

  现在可以制备多种光学纯肽，这些肽含有一个N-1H,1H-全氟烷基标签，标签位于选定的骨架酰胺键上。

  DOI：

  10.1039/b712617d

文献信息

• One-Pot 1,1-Dihydrofluoroalkylation of Amines Using Sulfuryl Fluoride
  作者：Maxim Epifanov、Paul J. Foth、Frances Gu、Charlotte Barrillon、Sahil S. Kanani、Carolyn S. Higman、Jason E. Hein、Glenn M. Sammis

  DOI：10.1021/jacs.8b11309

  日期：2018.12.5

  Sulfuryl fluoride, SO2F2, has been known and used as a fumigant for over 50 years but it has only recently gained widespread interest as a reagent for organic synthesis. Herein we report a novel application of sulfuryl fluoride gas in a new 1,1-dihydrofluoroalkylation reaction, which simply involves bubbling SO2F2 through a solution of amine, 1,1-dihydrofluoroalcohol, and diisopropylethylamine. The

  硫酰氟 (SO2F2) 已为人所知并用作熏蒸剂已有 50 多年的历史，但直到最近才作为有机合成试剂引起广泛关注。在此，我们报告了硫酰氟气体在新的 1,1-二氢氟烷基化反应中的新应用，该反应仅涉及将 SO2F2 鼓泡通过胺、1,1-二氢氟醇和二异丙基乙胺的溶液。该反应适用于广泛的伯胺和仲胺，以及几种 1,1-二氢氟醇，以 42% 至 80% 的分离产率提供 1,1-二氢氟烷基化胺。该反应还显示出优异的官能团耐受性。一锅活化和烷基化的简便性，加上广泛的底物范围，使这种新程序成为现有 1,1-二氢氟烷基化方法的有吸引力的替代方法。
• Construction of N-1H,1H-perfluoroalkylated peptide bonds
  作者：Changqing Lu、Darryl D. DesMarteau

  DOI：10.1039/b712617d

  日期：——

  The preparation of a variety of optically pure peptides containing an N-1H,1H-perfluoroalkyl label on a selected backbone amide bond is now possible.

  现在可以制备多种光学纯肽，这些肽含有一个N-1H,1H-全氟烷基标签，标签位于选定的骨架酰胺键上。
• The first example of linear peptides containing a N-trifluoroethylated backbone amide linkage and the surprising solution dynamics observed by 19F NMR
  作者：Changqing Lu、Darryl D. DesMarteau

  DOI：10.1016/j.jfluchem.2007.04.005

  日期：2007.7

  The alpha-amino group Of (L)phenylalanine methyl ester was trifluoroethylated using (2,2,2-trifluoroethyl)phenyliodonium N,N-bis(trifluoromethylsulfonyl)imide. A dipeptide Gly(L)Phe containing a trifluoroethylated peptide bond was synthesized by removing the alpha-amino proton of N-alpha-trifluoroethyl (L)phenylalanine methyl ester followed by coupling with N-alpha-phthaloyl glycine acid fluoride. The dipeptide was further coupled with (L)leucine methyl ester under conventional carboxyl activation conditions to provide two diastereomers of the tripeptide Gly(D,L)Phe(L)Leu. The solution dynamic behavior of the tripeptide was investigated as a function of solvents, by NOESY and variable temperature (VT) F-19 NMR experiments. (c) 2007 Elsevier B.V. All rights reserved.