(R)-2-amino-3-(trifluoromethylthio)propanoic acid | 144334-57-6

• 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: (R)-2-amino-3-(trifluoromethylthio)propanoic acid
• 英文别名: S-(trifluoromethyl)-L-cysteine；S-trifluoromethyl-L-cysteine；(2R)-2-amino-3-(trifluoromethylsulfanyl)propanoic acid
• CAS: 144334-57-6
• 化学式: C₄H₆F₃NO₂S
• mdl: MFCD11858219
• 分子量: 189.158
• InChiKey: KQKODVYODWEMMF-REOHCLBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-2-amino-3-(trifluoromethylthio)propanoic acid 、 N-(2-benzoylphenyl)-2-methyl-2-[[(1S)-1-phenylethyl]amino]propanamide 、 nickel(II) acetate tetrahydrate 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 以87%的产率得到
  参考文献：
  名称：

  Chemical deracemization and (S) to (R) interconversion of some fluorine-containing α-amino acids

  摘要：

  Several omega-CF3-substituted alpha-amino acids have been prepared in optically pure form via two complementary approaches. Racemic fluorinated derivatives of 2-aminobutanoic acid, norvaline and norleucine were chemically deracemized by complexation with a Ni(II) salt and a chiral reagent derived from alpha-(phenyl)ethylamine. Additionally this procedure also allowed the conversion of readily available L-amino acids, CF3-analogs of cysteine and methionine, into the corresponding unnatural D-series. Optically pure amino acids are obtained upon disassembly of the Ni(II) complexes with recovery of the chiral ligand. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2013.02.022
• 作为产物：
  描述：

  L-胱氨酸 、 三氟碘甲烷 在 氨 、 sodium 作用下， 反应 0.33h， 以65%的产率得到(R)-2-amino-3-(trifluoromethylthio)propanoic acid
  参考文献：
  名称：

  Simple preparation of trifluoromethionine and derivatives thereof

  摘要：

  公开了一种用于简单制备三氟甲硫氨酸及其类似物三氟甲基半胱氨酸、氟烷基同型半胱氨酸和氟烷基半胱氨酸以及它们的衍生物的方法。这些化合物是候选药物化合物或候选药物化合物的原料。具体地，通过在液氨中向光学活性或消旋半胱氨酸或半胱氨酸中添加金属钠，然后在伯奇还原条件下进一步添加氟烷基碘，可以简单方便地直接制备三氟甲硫氨酸、三氟甲基半胱氨酸、氟烷基同型半胱氨酸或氟烷基半胱氨酸，而无需经过同型半胱氨酸或半胱氨酸。

  公开号：

  US20110015433A1

文献信息

• Selective Radical Trifluoromethylation of Native Residues in Proteins
  作者：Mateusz Imiołek、Gogulan Karunanithy、Wai-Lung Ng、Andrew J. Baldwin、Véronique Gouverneur、Benjamin G. Davis

  DOI：10.1021/jacs.7b10230

  日期：2018.2.7

  fluorine incorporation would constitute a fast and efficient alternative. Here, we reveal a mild method for direct protein radical trifluoromethylation at native residues as a strategy for symmetric-multifluorine incorporation on mg scales with high recoveries. High selectivity toward tryptophan residues enhanced the utility of this direct trifluoromethylation technique allowing ready study of fluorinated

  氟的掺入不仅可以显着促进蛋白质的研究，还可以潜在地调节其功能。尽管一些生物合成方法允许全局残基替换，但翻译后氟掺入将构成快速且有效的替代方案。在这里，我们揭示了一种在天然残基上直接进行蛋白质自由基三氟甲基化的温和方法，作为毫克级对称多氟掺入的策略，具有高回收率。对色氨酸残基的高选择性增强了这种直接三氟甲基化技术的实用性，允许使用 19F-NMR 轻松研究氟化蛋白质构建体。
• Robust synthesis of trifluoromethionine and its derivatives by reductive trifluoromethylation of amino acid disulfides by CF3I/Na/Liq.NH3 system
  作者：Hiroyuki Yasui、Takeshi Yamamoto、Etsuko Tokunaga、Norio Shibata

  DOI：10.1016/j.jfluchem.2011.01.001

  日期：2011.3

  We disclose the reductive trifluoromethylation of chemically stable homocystine and cystine to provide corresponding trifluoromethyl ethers by the CF3I/Na/Liq.NH3 system. Both non-protected and protected homocystines can be nicely converted into trifluoromethylated methionines under the same condition. The method described offers a robust synthesis of pharmaceutically important trifluoromethionine, suitable for multigram synthesis. Pentafluoroethylation of homocystine was also achieved by the CF3CF2I/Na/Liq.NH3 system. (C) 2011 Elsevier B.V. All rights reserved.
• Simple preparation of trifluoromethionine and derivatives thereof
  申请人：SHIBATA Norio

  公开号：US20110015433A1

  公开（公告）日：2011-01-20

  Disclosed is a process for the simple preparation of trifluoromethionine, its analogs trifluoromethylcysteine, fluoroalkylhomocysteines, and fluoroalkylcysteines, and derivatives of them. These compounds are drug-candidate compounds or raw materials of drug-candidate compounds. Specifically, trifluoromethionine, trifluoromethylcysteine, a fluoroalkylhomocysteine, or a fluoroalkylcysteine is simply and conveniently prepared directly without passing through homocysteine or cysteine by adding metallic sodium to an optically active or racemic homocystine or cystine in liquid ammonia and further adding a fluoroalkyl iodide thereto under Birch reduction conditions.

  公开了一种用于简单制备三氟甲硫氨酸及其类似物三氟甲基半胱氨酸、氟烷基同型半胱氨酸和氟烷基半胱氨酸以及它们的衍生物的方法。这些化合物是候选药物化合物或候选药物化合物的原料。具体地，通过在液氨中向光学活性或消旋半胱氨酸或半胱氨酸中添加金属钠，然后在伯奇还原条件下进一步添加氟烷基碘，可以简单方便地直接制备三氟甲硫氨酸、三氟甲基半胱氨酸、氟烷基同型半胱氨酸或氟烷基半胱氨酸，而无需经过同型半胱氨酸或半胱氨酸。
• Chemical deracemization and (S) to (R) interconversion of some fluorine-containing α-amino acids
  作者：Alexander E. Sorochinsky、Hisanori Ueki、José Luis Aceña、Trevor K. Ellis、Hiroki Moriwaki、Tatsunori Sato、Vadim A. Soloshonok

  DOI：10.1016/j.jfluchem.2013.02.022

  日期：2013.8

  Several omega-CF3-substituted alpha-amino acids have been prepared in optically pure form via two complementary approaches. Racemic fluorinated derivatives of 2-aminobutanoic acid, norvaline and norleucine were chemically deracemized by complexation with a Ni(II) salt and a chiral reagent derived from alpha-(phenyl)ethylamine. Additionally this procedure also allowed the conversion of readily available L-amino acids, CF3-analogs of cysteine and methionine, into the corresponding unnatural D-series. Optically pure amino acids are obtained upon disassembly of the Ni(II) complexes with recovery of the chiral ligand. (C) 2013 Elsevier B.V. All rights reserved.