tert-butyl 2-(N-acetyl-2-tert-butylanilino)acetate | 1312576-42-3

• 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: tert-butyl 2-(N-acetyl-2-tert-butylanilino)acetate
• CAS: 1312576-42-3
• 化学式: C₁₈H₂₇NO₃
• 分子量: 305.417
• InChiKey: VPTUBQSECLCJHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-叔丁基苯胺 在 吡啶 、 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 26.0h， 生成 tert-butyl 2-(N-acetyl-2-tert-butylanilino)acetate
  参考文献：
  名称：

  Peptoid Atropisomers

  摘要：

  We report the isolation of N-aryl peptoid oligomers that adopt chiral folds, despite the absence of chiral centers. Peptoid monomers incorporating ortho-substituted N-aryl side chains are identified that exhibit axial chirality. We observe significant energy barriers to rotation about the stereogenic carbon-nitrogen bond, allowing chromatographic purification of stable atropisomeric forms. We study the atropisomerism of N-aryl peptoid oligomers by computational modeling, NMR, X-ray crystallography, dynamic HPLC, and circular dichroism. The results demonstrate a new approach to promote the conformational ordering of this important class of foldamer compounds.

  DOI：

  10.1021/ja2028684

文献信息

• Peptoid Atropisomers
  作者：Bishwajit Paul、Glenn L. Butterfoss、Mikki G. Boswell、P. Douglas Renfrew、Fanny G. Yeung、Neel H. Shah、Christian Wolf、Richard Bonneau、Kent Kirshenbaum

  DOI：10.1021/ja2028684

  日期：2011.7.20

  We report the isolation of N-aryl peptoid oligomers that adopt chiral folds, despite the absence of chiral centers. Peptoid monomers incorporating ortho-substituted N-aryl side chains are identified that exhibit axial chirality. We observe significant energy barriers to rotation about the stereogenic carbon-nitrogen bond, allowing chromatographic purification of stable atropisomeric forms. We study the atropisomerism of N-aryl peptoid oligomers by computational modeling, NMR, X-ray crystallography, dynamic HPLC, and circular dichroism. The results demonstrate a new approach to promote the conformational ordering of this important class of foldamer compounds.