(2R,3S)-(-)-3-Methyl-2-(trifluoroacetylamino)pent-4-enoic acid | 171964-10-6

• 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: (2R,3S)-(-)-3-Methyl-2-(trifluoroacetylamino)pent-4-enoic acid
• 英文别名: (2R,3S)-2-(2,2,2-trifluoroacetamido)-3-methylpent-4-enoic acid；(2R,3S)-3-methyl-2-(2,2,2-trifluoroacetamido)pent-4-enoic acid；(2R,3S)-3-Methyl [N-(Trifluoroacetyl)amino]pent-4-enoic acid；(2R,3S)-3-methyl-2-(trifluoroacetylamino)-4-pentenoic acid；(2R,3S)-2-(Trifluoroacetylamino)-3-methyl-4-pentenoic acid；(2R,3S)-3-methyl-2-[(2,2,2-trifluoroacetyl)amino]pent-4-enoic acid
• CAS: 171964-10-6
• 化学式: C₈H₁₀F₃NO₃
• 分子量: 225.168
• InChiKey: SJWVXFYBDFJOFF-CRCLSJGQSA-N

物化性质

• 沸点：
  320.3±42.0 °C(Predicted)
• 密度：
  1.298±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S)-(-)-3-Methyl-2-(trifluoroacetylamino)pent-4-enoic acid 在 sodium hydroxide 、 N,N'-羰基二咪唑 、 lithium diisopropyl amide 作用下， 生成 (4R,5S)-4-tert-Butoxycarbonylamino-5-methyl-3-oxo-hept-6-enoic acid benzyl ester
  参考文献：
  名称：

  A straightforward synthesis of protected isostatine from achiral precursors using the asymmetric chelate Claisen rearrangement

  摘要：

  Starting from achiral TFA-protected glycine crotyl ester (3) the interesting, suitable protected, enantiomerically pure beta-hydroxy-gamma-amino acid isostatine (7) was synthesized in only four steps. The amino acid obtained can directly be introduced into peptides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02486-1
• 作为产物：
  描述：

  (2E)-but-2-en-1-yl N-(2,2,2-trifluoroacetyl)glycinate 在 aluminum isopropoxide 、 lithium hexamethyldisilazane 、 奎宁 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,3S)-(-)-3-Methyl-2-(trifluoroacetylamino)pent-4-enoic acid
  参考文献：
  名称：

  Exploration of the Molecular Origin of the Azinomycin Epoxide: Timing of the Biosynthesis Revealed

  摘要：

  Streptomyces sahachiroi whole cell feeding experiments, utilizing putative precursors labeled with stable isotopes, established that the epoxide unit of the DNA cross-linked agents, azinomycin A and B, proceeds via a valine-dependent pathway and that hydroxylation and dehydration precedes formation of the terminal epoxide. Sodium 3-methyl-2-oxobutenoate, formed through a transimination reaction, was shown to be the penultimate precursor incorporated into the azinomycin epoxide.

  DOI：

  10.1021/ol8018852

文献信息

• Synthesis and Self-Assembling Properties of Polymerizable Organogelators
  作者：Guijun Wang、Andrew D. Hamilton

  DOI：10.1002/1521-3765(20020415)8:8<1954::aid-chem1954>3.0.co;2-x

  日期：2002.4.15

  In this paper we report the development of a family of polymerizable urea derivatives that are gelators for organic solvents. The design involves amino-acid-based urea derivatives containing methacrylate functional groups. Several of the bis-ureas show excellent gelation properties in a variety of organic solvents at very low concentrations (1.5 mM). The self-assembling properties of these compounds

  在本文中，我们报告了作为有机溶剂胶凝剂的可聚合脲衍生物家族的发展。设计涉及含有甲基丙烯酸酯官能团的基于氨基酸的脲衍生物。几种双脲在非常低的浓度（1.5 mM）的各种有机溶剂中显示出优异的胶凝特性。通过X射线粉末衍射，光学显微镜和电子显微镜研究了这些化合物的自组装性能。如扫描电子显微镜所示，分子自组装成纤维状聚集体。取决于单体单元的性质，聚集体的结构范围从小到大纤维和平面片。在极性溶剂中，分子表现出多层堆积模式。有机凝胶可以通过光辐照进行聚合，从而导致稳定性的显着提高，如相变温度的变化所示。观察到聚集体的形态在辐照之前和之后均保持相似的结构。该方法提供了具有设计的自组装结构的新型聚合物，并且还提供了稳定聚合物凝胶的途径。
• Stereoselective Synthesis of Proline-Derived Dipeptide Scaffolds (ProM-3 and ProM-7) Rigidified in a PPII Helix Conformation
  作者：Cédric Reuter、Margarethe Kleczka、Sarah de Mazancourt、Jörg-Martin Neudörfl、Ronald Kühne、Hans-Günther Schmalz

  DOI：10.1002/ejoc.201301875

  日期：2014.5

  diastereomeric scaffolds ProM-3 and ProM-7 were stereoselectively synthesized (as 9-fluorenylmethoxycarbonyl derivatives), and their configuration was unambiguously proven by means of X-ray crystallography. The required dehydroisoleucine building blocks were prepared by applying the enantioselective Kazmaier–Claisen rearrangement. The target compounds represent dipeptide analogs rigidified in a PPII helix conformation

  遵循基于肽偶联/复分解的策略，两个非对映体支架 ProM-3 和 ProM-7 被立体选择性地合成（作为 9-芴基甲氧基羰基衍生物），并且它们的构型通过 X 射线晶体学得到明确证明。所需的脱氢异亮氨酸构建块通过应用对映选择性 Kazmaier-Claisen 重排制备。目标化合物代表在 PPII 螺旋构象中刚性化的二肽类似物，这对于开发新的蛋白质模拟物很有意义，这些蛋白质模拟物选择性地结合专门用于识别采用 PPII 螺旋二级结构的配体的蛋白质结构域。
• Action of l-Aminoacylase and l-Amino Acid Oxidase on 2-Amino-3-methylpent-4-enoic acid [Δ(4)-Dehydroisoleucine and alloisoleucine] Stereoisomers: An Alternative Route to a Stereochemically Pure Compound and the Application to the Synthesis of (R)-2-Methylbutan-1-ol
  作者：Mikio Bakke

  DOI：10.1055/s-1999-3565

  日期：1999.9
• Total Synthesis of Cyclomarin C
  作者：Shi-Jun Wen、Zhu-Jun Yao

  DOI：10.1021/ol049065n

  日期：2004.8.1

  The total synthesis of cyclomarin C was accomplished through a convergent strategy from a tetrapeptide fragment and a tripeptide one. The developed methods to prepare the needed noncoded amino acids, the proper protection of peptide fragments, and identification of the optimum macrocylization site can be applied to further synthetic studies on other members of cyclomarins.
• Mues; Kazmaier, Synthesis, 2001, # 3, p. 487 - 498
  作者：Mues、Kazmaier

  DOI：——

  日期：——