N-(2-phenylethyl)-2-hydroxy-3-methyl-butanamide | 141330-03-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-(2-phenylethyl)-2-hydroxy-3-methyl-butanamide
• 英文别名: 2-hydroxy-3-methyl-N-phenethylbutanamide；2-hydroxy-3-methyl-N-(2-phenylethyl)butanamide
• CAS: 141330-03-2
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: RJVIWXUEZPZCLJ-UHFFFAOYSA-N

物化性质

• 沸点：
  415.4±38.0 °C(Predicted)
• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-羟基-3-甲基丁酸 在 吡啶 、 4-二甲氨基吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 、 柠檬酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 N-(2-phenylethyl)-2-hydroxy-3-methyl-butanamide
  参考文献：
  名称：

  A One Pot Procedure for the Synthesis of α-Hydroxyamides from the Corresponding α-Hydroxyacids

  摘要：

  Alpha-hydroxyamides are synthesized from the cooresponding alpha-hydroxyacids by generation of the bis-trimethylsilyl derivative and treating it with oxalyl chloride. Following addition of the appropriate amine, the TMS ether is hydrolyzed in the workup to provide the desired alpha-hydroxyamide. As summarized in Table 1, this reaction has proven to be general and compatible with chiral alpha-hydroxyacids affording the desired alpha-hydroxyamides in excellent yield (77-99%).

  DOI：

  10.1080/00397919208020850

文献信息

• The use of 2-hydroxymethyl benzoic acid as an effective water surrogate in the Passerini reaction: A straightforward access to α-hydroxyamides
  作者：Marta Serafini、Alessia Griglio、Elena Oberto、Tracey Pirali、Gian Cesare Tron

  DOI：10.1016/j.tetlet.2017.11.021

  日期：2017.12

  over the years, but they share common drawbacks in terms of generality and tolerability, especially to acid labile functionalities. Here we report a truncated Passerini reaction suitable for the easy and mild preparation of functionalized α-hydroxyamides. In particular, this procedure is tolerant to acid sensitive protecting groups, which remain intact during the multicomponent reaction.

  多年来，已经描述了用于合成α-羟基酰胺的数十种策略，但是它们在通用性和耐受性（尤其是对酸不稳定的功能性）方面具有共同的缺点。在这里，我们报告截短的Passerini反应，适用于轻松温和地制备官能化的α-羟基酰胺。特别地，该方法耐受酸敏感性保护基，其在多组分反应期间保持完整。
• Unconventional Passerini Reaction toward α-Aminoxy-amides
  作者：Ajay L. Chandgude、Alexander Dömling

  DOI：10.1021/acs.orglett.6b03293

  日期：2016.12.16

  The Passerini multicomponent reaction (P-3CR) toward the one-step synthesis of alpha-aminoxy-amide, by employing for the first time a N-hydroxamic acid component, has been reported. The sonication-accelerated, catalyst-free, simple, fast, and highly efficient Passerini reaction is used for the synthesis of diverse alpha-aminoxy-amides. The reaction is compatible with a vast range of aldehydes, isocyanides, and N-hydroxamic acids such as N-hydroxysuccinimides and phthalimides. The generated Passerini products can be easily converted into several follow-up products.