N-(S)-(2-hydroxy-1-methylethyl)-2,2.2-trifluoroacetamide | 107011-25-6

• 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-(S)-(2-hydroxy-1-methylethyl)-2,2.2-trifluoroacetamide
• 英文别名: N-trifluoroacetyl-(2S)-alaninol；Acetamide, 2,2,2-trifluoro-N-[(1S)-2-hydroxy-1-methylethyl]-；2,2,2-trifluoro-N-[(2S)-1-hydroxypropan-2-yl]acetamide
• CAS: 107011-25-6
• 化学式: C₅H₈F₃NO₂
• 分子量: 171.119
• InChiKey: FQZGFKHGAHLJBN-VKHMYHEASA-N

物化性质

• 熔点：
  80 °C(Solv: acetonitrile (75-05-8))
• 沸点：
  228.7±40.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(S)-(2-hydroxy-1-methylethyl)-2,2.2-trifluoroacetamide 在 咪唑 、 碘 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 1.25h， 以79%的产率得到N-((1S)-2-iodo-1-methylethyl)trifluoroacetamide
  参考文献：
  名称：

  Probing Molecular Interactions within Class II MHC A^q/Glycopeptide/T-Cell Receptor Complexes Associated with Collagen-Induced Arthritis

  摘要：

  T cells obtained in a mouse model for rheumatoid arthritis are activated by a glycopeptide fragment from rat type II collagen (CII) bound to the class II major histocompatibility complex A(q) molecule. We report a comparative model of A(q) in complex with the glycopeptide CII260-267. This model was used in a structure-based design approach where the amide bond between Ala(261) and Gly(262) in the glycopeptide was selected for replacement with psi[COCH2], psi[CH2NH2+], and psi[(E)-CH=CH] isosteres. Ala-Gly isostere building blocks were then synthesized and introduced in CII260-267 and CII259-273 glycopeptides. The modified glycopeptides were evaluated for binding to the A(q) molecule, and the results were interpreted in view of the A(q)/glycopeptide model. Moreover, recognition by a panel of T-cell hybridomas revealed high sensitivity for the backbone modifications. These studies contribute to the understanding of the interactions in the ternary A(q)/glycopeptide/T-cell receptor complexes that activate T cells in autoimmune arthritis and suggest possibilities for new vaccination approaches.

  DOI：

  10.1021/jm0705410
• 作为产物：
  描述：

  N-vinyl-trifluoroacetamide 在 sodium tetrahydroborate 作用下， 生成 N-(S)-(2-hydroxy-1-methylethyl)-2,2.2-trifluoroacetamide
  参考文献：
  名称：

  使用手性二氮杂磷烷配体对 N-乙烯基甲酰胺、烯丙基氨基甲酸酯和烯丙基醚进行对映选择性加氢甲酰化

  摘要：

  二氮杂磷烷配体的铑配合物催化 N-乙烯基羧酰胺、烯丙基醚和烯丙基氨基甲酸酯的不对称加氢甲酰化；产品包括 1,2- 和 1,3- 氨基醛和 1,3- 烷氧基醛。使用玻璃压力瓶、较短的反应时间（通常小于 6 小时）和低催化剂负载（通常为 0.5 mol%），20 种底物成功转化为具有有用的区域选择性和高对映选择性（高达 99% ee）的手性醛。手性罗氏醛是通过烯丙基甲硅烷基醚的加氢甲酰化得到 97% ee 的。通常困难的底物，如 1,1- 和 1,2- 二取代烯烃，在六个例子中进行了有效的加氢甲酰化，ee 为 89-97%，并完全转化。

  DOI：

  10.1021/ja106674n

文献信息

• Chirality-directed organogel formation
  作者：Remir G. Kostyanovsky、Denis A. Lenev、Oleg N. Krutius、Andrey A. Stankevich

  DOI：10.1070/mc2005v015n04abeh002136

  日期：2005.1

  New low molecular mass enantiopure organogelators (1R,4R)-1, (S)-2, (R)-3 and (R)-4 were found; racemates (R,S)-3 and (R,S)-4 have only a moderate gelating power, whereas (R,S)-1 and (R,S)-2 do not show gelating properties at all.
• Trifluoroacetylation of amines and amino acids by polymer-bound trifluoroacetylation reagents
  作者：Polina I. Svirskaya、Clifford C. Leznoff、Martin Steinman

  DOI：10.1021/jo00383a042

  日期：1987.4
• SVIRSKAYA P. I.; LEZNOFF C. C.; STEINMAN M., J. ORG. CHEM., 52,(1987) N 7, 1362-1364
  作者：SVIRSKAYA P. I.、 LEZNOFF C. C.、 STEINMAN M.

  DOI：——

  日期：——
• Probing Molecular Interactions within Class II MHC A^q/Glycopeptide/T-Cell Receptor Complexes Associated with Collagen-Induced Arthritis
  作者：Ida E. Andersson、Balik Dzhambazov、Rikard Holmdahl、Anna Linusson、Jan Kihlberg

  DOI：10.1021/jm0705410

  日期：2007.11.1

  T cells obtained in a mouse model for rheumatoid arthritis are activated by a glycopeptide fragment from rat type II collagen (CII) bound to the class II major histocompatibility complex A(q) molecule. We report a comparative model of A(q) in complex with the glycopeptide CII260-267. This model was used in a structure-based design approach where the amide bond between Ala(261) and Gly(262) in the glycopeptide was selected for replacement with psi[COCH2], psi[CH2NH2+], and psi[(E)-CH=CH] isosteres. Ala-Gly isostere building blocks were then synthesized and introduced in CII260-267 and CII259-273 glycopeptides. The modified glycopeptides were evaluated for binding to the A(q) molecule, and the results were interpreted in view of the A(q)/glycopeptide model. Moreover, recognition by a panel of T-cell hybridomas revealed high sensitivity for the backbone modifications. These studies contribute to the understanding of the interactions in the ternary A(q)/glycopeptide/T-cell receptor complexes that activate T cells in autoimmune arthritis and suggest possibilities for new vaccination approaches.
• Enantioselective Hydroformylation of <i>N</i>-Vinyl Carboxamides, Allyl Carbamates, and Allyl Ethers Using Chiral Diazaphospholane Ligands
  作者：Richard I. McDonald、Gene W. Wong、Ram P. Neupane、Shannon S. Stahl、Clark R. Landis

  DOI：10.1021/ja106674n

  日期：2010.10.13

  Rhodium complexes of diazaphospholane ligands catalyze the asymmetric hydroformylation of N-vinyl carboxamides, allyl ethers, and allyl carbamates; products include 1,2- and 1,3-aminoaldehydes and 1,3-alkoxyaldehydes. Using glass pressure bottles, short reaction times (generally less than 6 h), and low catalyst loading (commonly 0.5 mol %), 20 substrates are successfully converted to chiral aldehydes

  二氮杂磷烷配体的铑配合物催化 N-乙烯基羧酰胺、烯丙基醚和烯丙基氨基甲酸酯的不对称加氢甲酰化；产品包括 1,2- 和 1,3- 氨基醛和 1,3- 烷氧基醛。使用玻璃压力瓶、较短的反应时间（通常小于 6 小时）和低催化剂负载（通常为 0.5 mol%），20 种底物成功转化为具有有用的区域选择性和高对映选择性（高达 99% ee）的手性醛。手性罗氏醛是通过烯丙基甲硅烷基醚的加氢甲酰化得到 97% ee 的。通常困难的底物，如 1,1- 和 1,2- 二取代烯烃，在六个例子中进行了有效的加氢甲酰化，ee 为 89-97%，并完全转化。