N-((1S,2S)-1-bromomethyl-2-methylbutyl)trifluoroacetamide | 1330117-00-4

• 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-((1S,2S)-1-bromomethyl-2-methylbutyl)trifluoroacetamide
• 英文别名: N-[(2S,3S)-1-bromo-3-methylpentan-2-yl]-2,2,2-trifluoroacetamide
• CAS: 1330117-00-4
• 化学式: C₈H₁₃BrF₃NO
• 分子量: 276.097
• InChiKey: AINAORKEKFNEBK-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-((1S,2S)-1-bromomethyl-2-methylbutyl)trifluoroacetamide 在 chromium(VI) oxide 、 正丁基锂 、 硫酸 、 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 124.42h， 生成
  参考文献：
  名称：

  (E)-Alkene and Ethylene Isosteres Substantially Alter the Hydrogen-Bonding Network in Class II MHC A^q/Glycopeptide Complexes and Affect T-Cell Recognition

  摘要：

  The structural basis for antigen presentation by class II major histocompatibility complex (MHC) proteins to CD4(+) T-cells is important for understanding and possibly treating autoimmune diseases. In the work described in this paper, (E)-alkene and ethylene amide-bond isosteres were used to investigate the effect of removing hydrogen-bonding possibilities from the CII259-270 glycopeptide, which is bound by the arthritis-associated murine A(q) class II MHC protein. The isostere-modified glycopeptides showed varying and unexpectedly large losses of A(q) binding that could be linked to the dynamics of the system. Molecular dynamics (MD) simulations revealed that the backbone of CII259-270 and the A(q) protein are able to form up to 11 hydrogen bonds, but fewer than this number are present at any one time. Most of the strong hydrogen-bond interactions were formed by the N-terminal part of the glycopeptide, i.e., in the region where the isosteric replacements were made. The structural dynamics also revealed that hydrogen bonds were strongly coupled to each other; the loss of one hydrogen-bond interaction had a profound effect on the entire hydrogen-bonding network. The A(q) binding data revealed that an ethylene isostere glycopeptide unexpectedly bound more strongly to A(q) than the corresponding (E)-alkene, which is in contrast to the trend observed for the other isosteres. Analysis of the MD trajectories revealed that the complex conformation of this ethylene isostere was structurally different and had an altered molecular interaction pattern compared to the other A(q)/glycopeptide complexes. The introduced amide-bond isosteres also affected the interactions of the glycopeptide/A(q) complexes with T-cell receptors. The dynamic variation of the patterns and strengths of the hydrogen-bond interactions in the class II MHC system is of critical importance for the class II MHC/peptide/TCR signaling system.

  DOI：

  10.1021/ja2038722
• 作为产物：
  描述：

  L-异亮氨醇 在 四溴化碳 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 56.5h， 生成 N-((1S,2S)-1-bromomethyl-2-methylbutyl)trifluoroacetamide
  参考文献：
  名称：

  (E)-Alkene and Ethylene Isosteres Substantially Alter the Hydrogen-Bonding Network in Class II MHC A^q/Glycopeptide Complexes and Affect T-Cell Recognition

  摘要：

  The structural basis for antigen presentation by class II major histocompatibility complex (MHC) proteins to CD4(+) T-cells is important for understanding and possibly treating autoimmune diseases. In the work described in this paper, (E)-alkene and ethylene amide-bond isosteres were used to investigate the effect of removing hydrogen-bonding possibilities from the CII259-270 glycopeptide, which is bound by the arthritis-associated murine A(q) class II MHC protein. The isostere-modified glycopeptides showed varying and unexpectedly large losses of A(q) binding that could be linked to the dynamics of the system. Molecular dynamics (MD) simulations revealed that the backbone of CII259-270 and the A(q) protein are able to form up to 11 hydrogen bonds, but fewer than this number are present at any one time. Most of the strong hydrogen-bond interactions were formed by the N-terminal part of the glycopeptide, i.e., in the region where the isosteric replacements were made. The structural dynamics also revealed that hydrogen bonds were strongly coupled to each other; the loss of one hydrogen-bond interaction had a profound effect on the entire hydrogen-bonding network. The A(q) binding data revealed that an ethylene isostere glycopeptide unexpectedly bound more strongly to A(q) than the corresponding (E)-alkene, which is in contrast to the trend observed for the other isosteres. Analysis of the MD trajectories revealed that the complex conformation of this ethylene isostere was structurally different and had an altered molecular interaction pattern compared to the other A(q)/glycopeptide complexes. The introduced amide-bond isosteres also affected the interactions of the glycopeptide/A(q) complexes with T-cell receptors. The dynamic variation of the patterns and strengths of the hydrogen-bond interactions in the class II MHC system is of critical importance for the class II MHC/peptide/TCR signaling system.

  DOI：

  10.1021/ja2038722

文献信息

• Amino Acid-Derived Phosphonium Salts-Catalyzed Michael Addition of 3-Substituted Oxindoles
  作者：Xiaoyu Wu、Qin Liu、Yong Liu、Qun Wang、Ying Zhang、Jie Chen、Weiguo Cao、Gang Zhao

  DOI：10.1002/adsc.201300383

  日期：2013.9.16

  catalyst prepared from easily available chiral amino acids was evaluated in a model reaction between oxindole and methyl vinyl ketone, and the catalyst derived from isoleucine was found to be the best. Michael additions of 3‐monosubstituted oxindoles to methyl vinyl ketone, acrolein or propargyl aldehyde proceeded smoothly to afford 3,3‐disubstituted oxindoles in good to excellent yields with moderate

  在羟吲哚与甲基乙烯基酮之间的模型反应中，评估了一种由易得的手性氨基酸制得的新型phospho相转移催化剂，发现异亮氨酸衍生的催化剂是最好的。在甲基乙烯基酮，丙烯醛或炔丙基醛中将3-单取代的羟吲哚迈克尔加成反应顺利进行，得到3,3-二取代的羟吲哚，收率良好至优异，中等至优异ee s。