N-(2'-hydroxyethyl)-N-butylpentamide

• 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'-hydroxyethyl)-N-butylpentamide
• 英文别名: N-butyl-N-(2-hydroxyethyl)pentanamide
• 化学式: C₁₁H₂₃NO₂
• 分子量: 201.309
• InChiKey: ARQZKZIGHXIWOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-壬酮 、 2-叠氮基乙醇 在 三氟化硼乙醚 、 碳酸氢钠 作用下， 生成 2-butylaminoethylpentanoate 、 N-(2'-hydroxyethyl)-N-butylpentamide
  参考文献：
  名称：

  Hydrolysis of Iminium Ethers Derived from the Reaction of Ketones with Hydroxy Azides:  Synthesis of Macrocyclic Lactams and Lactones

  摘要：

  The hydrolysis of iminium ether intermediates formed by a nitrogen insertion sequence involving azido alcohols 1 or 2 and ketones was investigated. Ketones containing 6-12-membered rings were surveyed and shown to provide lactams and lactones in good to excellent overall yield. Reactions employing acetone or 5-nonanone gave similar results, generating analogous amides and esters. The relative amounts of lactone vs lactam produced in a given reaction were found to depend on the structures of the reactants and the pH of the basic media used to hydrolyze the iminium ethers. A mechanism accounting for the formation of each product is discussed in terms of ring strain and the protonation state of ortho ester animal intermediates.

  DOI：

  10.1021/jo990041h

文献信息

• Reactions of Oxazolinium and Dihydrooxazinium Salts Prepared by an Azide Insertion Sequence: pH Control of Product Distribution
  作者：Jennifer E. Forsee

  DOI：10.1055/s-1998-1925

  日期：1998.11