N-[1-(cyclohexylamino)-4-methyl-1-oxopentan-2-yl]benzamide | 916162-07-7

• 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-[1-(cyclohexylamino)-4-methyl-1-oxopentan-2-yl]benzamide
• 英文别名: (S)-N-(1-(cyclohexylamino)-4-methyl-1-oxopentan-2-yl)benzamide；N-[(2S)-1-(cyclohexylamino)-4-methyl-1-oxopentan-2-yl]benzamide
• CAS: 916162-07-7
• 化学式: C₁₉H₂₈N₂O₂
• 分子量: 316.444
• InChiKey: GVTRWPUBZKOSQH-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-[1-(cyclohexylamino)-4-methyl-1-oxopentan-2-yl]-N-[1-(2,4-dimethoxyphenyl)ethyl]benzamide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到N-[1-(cyclohexylamino)-4-methyl-1-oxopentan-2-yl]benzamide
  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

• Amidation of α-Amino Acids Using Dichloro(methyl)(3,3,3-trifluoropropyl)silane and Imidazole without Conventional Protection and Deprotection of α-Amino Group
  作者：Tomoya Nobuta、Honoka Morishita、Yutaka Suto、Noriyuki Yamagiwa

  DOI：10.1055/a-1865-1792

  日期：2022.9

  Amidation of amino acids using dichloro(methyl)(3,3,3-trifluoropropyl)silane (MTFPSCl2) and imidazole is described. MTFPSCl2 activates the carboxy group and protects the α-amino group of amino acids. The amidation proceeded with 19 amino acids and 19 amines, including α-branched amines and anilines; the corresponding amino acid amides were synthesized in good-to-high yields (up to 96%) with low-to-no

  描述了使用二氯（甲基）（3,3,3-三氟丙基）硅烷（MTFPSCl 2）和咪唑对氨基酸进行酰胺化。MTFPSCl 2活化羧基并保护氨基酸的α-氨基。酰胺化进行了19个氨基酸和19个胺，包括α-支化胺和苯胺；相应的氨基酸酰胺以高至高产率（高达 96%）合成，外消旋化低至无。