(S)-3-Methyl-2-(2,2,2-trifluoro-acetylamino)-butyric acid isopropyl ester | 53375-31-8

• 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: (S)-3-Methyl-2-(2,2,2-trifluoro-acetylamino)-butyric acid isopropyl ester
• 英文别名: propan-2-yl (2S)-3-methyl-2-[(2,2,2-trifluoroacetyl)amino]butanoate
• CAS: 53375-31-8
• 化学式: C₁₀H₁₆F₃NO₃
• 分子量: 255.237
• InChiKey: JQOBSGRWMHFMQK-ZETCQYMHSA-N

物化性质

• 沸点：
  265.8±40.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  L-缬氨酸 在 acid 作用下， 以 二氯甲烷 为溶剂， 反应 1.17h， 生成 (S)-3-Methyl-2-(2,2,2-trifluoro-acetylamino)-butyric acid isopropyl ester
  参考文献：
  名称：

  通过气相色谱/燃烧/同位素比质谱对氨基酸对映体进行稳定的氮同位素分析。

  摘要：

  提出了通过使用气相色谱/燃烧/同位素比质谱法（GC / C / IRMS）分析单个氨基酸立体异构体的稳定氮同位素组成的方法。单个氨基酸或其对映异构体的氮同位素组成可能不需要常规稳定同位素分析所需的劳动强度大且耗时的制备规模的色谱程序。在水解和衍生化之后，利用气相色谱分离的流出物流，对纳摩尔量的每种氨基酸立体异构体进行单组分同位素分析。在氨基酸酰化过程中，氮同位素的分馏极少，没有化学计量地将额外的氮添加到衍生物中。因此，衍生物中氮的同位素组成与原始化合物相同。通过常规同位素比质谱法（IRMS）和GC / C / IRMS对11个氨基酸及其三氟乙酰基（TFA）/异丙基（IP）酯衍生物进行了重复的稳定氮同位素分析，结果表明，气相色谱程序可高度重现（标准偏差通常为每千分之0.3-0.4），而氨基酸与其TFA / IP衍生物之间的同位素差异通常小于每千分之0.5。

  DOI：

  10.1021/ac960956l

文献信息

• Nucleophilic Substitution Reactions of Alkyl Halides by Using New Polymer-Supported Reagents Containing Hemin
  作者：Kiyoshi Saito、Kaoru Harada

  DOI：10.1246/bcsj.62.2562

  日期：1989.8

  hemin, divinylbenzene, and 2-methyl-5-vinylpyridine was synthesized by suspension copolymerization. Substitution reactions of primary, secondary, and tertiary alkyl halides with the hemin copolymer combined with cyanide, azide, and thiocyanate ions were given satisfactory yields. This reaction mechanism was revealed to be a SNi type on the basis of stereochemical study. The hemin copolymer was not only

  通过悬浮共聚反应合成了一种由氯化血红素、二乙烯基苯和2-甲基-5-乙烯基吡啶组成的新型高分子试剂。伯、仲和叔烷基卤与氯化血红素共聚物与氰化物、叠氮化物和硫氰酸根离子的取代反应得到了令人满意的产率。根据立体化学研究，该反应机理被揭示为 SNi 型。氯化血红素共聚物不仅是具有功能性的聚合物负载试剂，而且还用于将产物与反应混合物分离。
• Metal-Organic Framework Co(<scp>D</scp>-Cam)_1/2(bdc)_1/2(tmdpy) for Improved Enantioseparations on a Chiral Cyclodextrin Stationary Phase in Gas Chromatography
  作者：Hong Liu、Sheng-Ming Xie、Ping Ai、Jun-Hui Zhang、Mei Zhang、Li-Ming Yuan

  DOI：10.1002/cplu.201402067

  日期：2014.8

  peramylated β‐cyclodextrin+MOF shows excellent selectivity for the recognition of racemates, and higher resolutions are achieved on the peramylated β‐cyclodextrin+MOF stationary phase. Experimental results indicate that the use of Co(D‐Cam)1/2(bdc)1/2(tmdpy) can improve enantioseparations on peramylated β‐cyclodextrins. This is the first report that chiral MOFs can improve enantioseparations on a chiral stationary

  初步努力结合手性金属-有机构架（MOF），钴（d -Cam）1/2（BDC）1/2（tmdpy）（d -Cam = d樟脑酸，BDC = 1,4-苯二甲酸，tmdpy = 4,4'-三亚甲基二吡啶），用过酰胺化的β-环糊精来研究MOF的使用是否可以增强对环糊精固定相的对映体分离。与掺入含有氯化钠的MOF中的高酰化β-环糊精色谱柱相比，高酰化β-环糊精+ MOF色谱柱对外消旋体的识别具有出色的选择性，并且在高酰化的β-环糊精+ MOF固定相上实现了更高的分离度。实验结果表明，Co（D‐Cam）1/2（bdc ）1/2（tmdpy）可以改善对氨基甲酸酯化的β-环糊精的对映体分离。这是第一个报道，手性MOF可以改善手性固定相上的对映体分离，用于色谱分离。
• Stable carbon isotope analysis of amino acid enantiomers by conventional isotope ratio mass spectrometry and combined gas chromatography/isotope ratio mass spectrometry
  作者：J. A. Silfer、M. H. Engel、S. A. Macko、E. J. Jumeau

  DOI：10.1021/ac00004a014

  日期：1991.2.15

  The application of a combined gas chromatography/isotope ratio mass spectrometry (GC/IRMS) method for stable carbon isotope analysis of amino acid enantiomers is presented. This method eliminates the numerous preparative steps integral to the isolation of amino acids and amino acid enantiomers from protein hydrolyzates that precede delta-C-13 analysis by conventional isotope ratio mass spectrometry. Unlike hydrocarbons, amino acids require derivatization prior to GC/IRMS analysis. Replicate delta-C-13 analyses of trifluoroacetyl (TFA) isopropyl ester derivatives of 22 amino acids by IRMS revealed that the derivatization process is reproducible, with an average error (1 standard deviation) of 0.10% +/- 0.09%. The average analytical error for analysis of amino acid derivatives by GC/IRMS was 0.26% +/- 0.09%. In general, absolute differences between IRMS and GC/IRMS analyses were less than 0.5%. The derivatization process introduces a distinct, reproducible isotopic fractionation that is constant for each amino acid type. The observed fractionations preclude direct calculation of underivatized amino acid delta-C-13 values from their respective TFA isopropyl ester delta-C-13 compositions through mass balance relationships. Derivatization of amino acid standards of known stable carbon isotope compositions in conjunction with natural samples, however, permits computation of the original, underivatized amino acid delta-C-13 values through use of an empirical correction for the carbon introduced during the derivatization process.
• 3D-structure of cycloreticulin C and glabrin A, cyclopeptides from the seeds of Annona reticulata
  作者：Alassane Wélé、Claudine Mayer、Dermigny Quentin、Yanjun Zhang、Alain Blond、Bernard Bodo

  DOI：10.1016/j.tet.2008.10.055

  日期：2009.1

  Two cyclopeptides, the cycloheptapeptide cycloreticulin C, cyclo(Pro(1)-Gly(2)-Gln(3)-Pro(4)-Pro(5)-Tyr(6)-Val(7)) (1), and the cyclohexapeptide glabrin A, cyclo(Pro(1)-Gly(2)-Leu(3)-Val(4)-Ile(5)-Tyr(6)) (2), have been isolated from the methanol extract of the seeds of Annona reticulata. Their Structures were elucidated on the basis of the MS/MS fragmentation using a Q-TOF mass spectrometer equipped with an ESI Source, chemical degradation and extensive 2D-NMR. The solution conformation of cycloreticulin C involves two beta-turns, one of type II with trans-Pro(1) and Gly(2) at the corners, another of type VIa with trans-Pro(4) and cis-Pro(5) at the corners, and followed by a beta-bulge at the Tyr(6)-Val(7) level. The solid state and solution conformations of glabrin A have been analyzed by X-ray and 2D-NMR studies, respectively, and are characterized by the presence of two beta-turns, the first of type VIa and the second intermediary between types I and III at the solid state and a gamma-turn in solution. (C) 2008 Elsevier Ltd. All rights reserved.
• Williams, Dudley H.; Santikarn, Sitthivet; Angelis, Francesco De, Journal of the Chemical Society. Perkin transactions I, 1983, # 8, p. 1869 - 1878
  作者：Williams, Dudley H.、Santikarn, Sitthivet、Angelis, Francesco De、Smith, Richard J.、Reid, David G.、at al.

  DOI：——

  日期：——