N-trifluoroacetyl methyl ester of (R)-valine | 81083-97-8

• 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: N-trifluoroacetyl methyl ester of (R)-valine
• 英文别名: N-TFA-D-Val-OMe；methyl (2R)-3-methyl-2-[(2,2,2-trifluoroacetyl)amino]butanoate
• CAS: 81083-97-8
• 化学式: C₈H₁₂F₃NO₃
• 分子量: 227.183
• InChiKey: KCASHPNYDVOBJR-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-trifluoroacetyl-(S)-valine methyl ester 、 N-trifluoroacetyl methyl ester of (R)-valine 生成 N-Trifluoracetyl-valin-methylester
  参考文献：
  名称：

  KOPPENHOEFER, B.;TRETTIN, U., FRESENIUS Z. ANAL. CHEM., 333,(1989) N, C. 750

  摘要：

  DOI：
• 作为产物：
  描述：

  D-缬氨酸 在 氯化亚砜 作用下， 生成 N-trifluoroacetyl methyl ester of (R)-valine
  参考文献：
  名称：

  Chiral Discrimination in the Liquid Phase: Excess Volumes of Binary Mixtures of Amino Acid Derivatives

  摘要：

  Volume changes on mixing the enantiomers of N-trifluoroacetylamino acid methyl esters (N-TFA-amino acid-OMe) were determined at 25 degrees C by means of a high-precision vibrating-tube densimeter. The excess molar volumes (V-E) for the racemic mixtures of N-TFA-Ala-OMe 1, N-TFA-Val-OMe 2, and N-TFA-Leu-OMe 3, were found as V-E = 0.0098, -0.0458, and 0.035 cm(3) mol(-1), respectively. For 2 and 3, these volumetric effects of discriminating interactions between enantiomers in the liquid phase are the largest ever observed.

  DOI：

  10.1021/j100078a031

文献信息

• An enantioselective synthesis of (S)-4-fluorohistidine
  作者：Jan Hajduch、John C. Cramer、Kenneth L. Kirk

  DOI：10.1016/j.jfluchem.2008.04.011

  日期：2008.9

  We report a new synthesis of enantiomerically pure (S)-4-fluorohisitidine based on diastereoselective alkylation of MOM-protected 4-fluoro-5-bromomethyl imidazole using the Schollkopf bis-lactim amino acid synthesis. Improvements in procedures for preparation of key intermediates are also described. (S)-4-Fluorohisitidine prepared by this new method was identical in all respects to material prepared

  我们报告了基于 MOM 保护的 4-氟-5-溴甲基咪唑的非对映选择性烷基化的对映体纯 (S)-4-氟组氨酸的新合成，使用 Schollkopf 双内酰胺氨基酸合成。还描述了关键中间体制备程序的改进。通过这种新方法制备的 (S)-4-氟组氨酸在所有方面都与通过先前程序制备的材料相同。
• Cycloforskamide, a Cytotoxic Macrocyclic Peptide from the Sea Slug <i>Pleurobranchus forskalii</i>
  作者：Karen Co Tan、Toshiyuki Wakimoto、Kentaro Takada、Takashi Ohtsuki、Nahoko Uchiyama、Yukihiro Goda、Ikuro Abe

  DOI：10.1021/np400404r

  日期：2013.7.26

  A macrocylic dodecapeptide, cycloforskamide, was isolated from the sea slug Pleurobranchus forskalii, collected off Ishigaki Island, Japan. Its planar structure was deduced by extensive NMR analyses and was further confirmed by MS/MS fragmentation analyses. Finally, the absolute configuration was determined by total hydrolysis and chiral-phase gas chromatographic analysis. This novel dodecapeptide contains three D-amino acids and three thiazoline heterocycles and exhibits cytotoxicity against murine leukemia P388 cells, with an IC50 of 5.8 mu M.
• Kinetic Resolution of Protected α-Amino Acid Derivatives by a Chiral <i>O</i>-Nucleophilic Acyl Transfer Catalyst
  作者：Gregory T. Notte、Tarek Sammakia

  DOI：10.1021/ja058010t

  日期：2006.4.5

  The kinetic resolution of alpha-trifluoroacetamido N-acyl oxazolidinethiones using 5-10% of the chiral, nonracemic O-nucleophilic acyl transfer catalyst 2 is described. A variety of substrates participate in this reaction in excellent yields, with s-factors ranging from 20 to 86.