ethyl {[2-(acryloylamino)-4-methylpentanoyl]amino}acetate | 1598420-57-5

• 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: ethyl {[2-(acryloylamino)-4-methylpentanoyl]amino}acetate
• 英文别名: ethyl 2-[[(2S)-4-methyl-2-(prop-2-enoylamino)pentanoyl]amino]acetate
• CAS: 1598420-57-5
• 化学式: C₁₃H₂₂N₂O₄
• 分子量: 270.329
• InChiKey: CKUAVIYROUDZGM-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 2-[2-{N-(1-[2,4-dimethoxyphenyl]ethyl)acrylamido}-4-methylpentanamido]acetate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以55%的产率得到ethyl {[2-(acryloylamino)-4-methylpentanoyl]amino}acetate
  参考文献：
  名称：

  Chemoenzymatic synthesis and application of a new, easily chiral auxiliary for the synthesis of peptidomimetics via an Ugi reaction

  摘要：

  A new chiral auxiliary derived from alpha-phenylethylamine, alpha-(2,4-dimethoxyphenyl)ethylamine is presented. It significantly expands upon the application of cc-phenylethylamine derivatives used as chiral auxiliaries. A straightforward, chemoenzymatic synthesis of non-racemic alpha-(2,4-dimethoxyphenyl)ethylamine is described and the new chiral auxiliary applied to an asymmetric Ugi reaction. The mild conditions used for the cleavage of the auxiliary allowed to obtain chiral, non-racemic peptidomimetics possessing reactive alpha,beta-unsaturated double bonds.(C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.01.016

文献信息

• Chemoenzymatic synthesis and application of a new, easily chiral auxiliary for the synthesis of peptidomimetics via an Ugi reaction
  作者：Szymon Klossowski、Anna Brodzka、Małgorzata Zysk、Ryszard Ostaszewski

  DOI：10.1016/j.tetasy.2014.01.016

  日期：2014.3

  A new chiral auxiliary derived from alpha-phenylethylamine, alpha-(2,4-dimethoxyphenyl)ethylamine is presented. It significantly expands upon the application of cc-phenylethylamine derivatives used as chiral auxiliaries. A straightforward, chemoenzymatic synthesis of non-racemic alpha-(2,4-dimethoxyphenyl)ethylamine is described and the new chiral auxiliary applied to an asymmetric Ugi reaction. The mild conditions used for the cleavage of the auxiliary allowed to obtain chiral, non-racemic peptidomimetics possessing reactive alpha,beta-unsaturated double bonds.(C) 2014 Elsevier Ltd. All rights reserved.