β-propiolactam hydroiodide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: β-propiolactam hydroiodide
• 化学式: C₃H₅NO*HI
• 分子量: 198.991
• InChiKey: YZNDXBDQULDHKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.12
• 重原子数：
  6.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  乙酰碘 、 β-丙氨酸 以 乙腈 为溶剂， 反应 1.0h， 以1.3 g的产率得到β-propiolactam hydroiodide
  参考文献：
  名称：

  Acyl iodides in organic synthesis: VIII. Reactions with amino acids

  摘要：

  Reactions of acyl iodides RCOI (R=Me, Ph) with glycine, beta-alanine, and gamma-aminobutyric acid were investigated. The reaction proceeded easily at room temperature without solvent involving both functional groups H2N and COOH. The prevalence of one of the reaction directions depends on the acidity of the amino acid. The more acidic glycine (pK(a) 2.4) reacts with RCOI affording mainly N-acylated product, whereas beta-alanine (pK(a) 3.60) and especially gamma-aminobutyric acid (pK(a) 4.06) are predominantly involved into exchange iodination furnishing the corresponding aminoacyl iodides.

  DOI：

  10.1134/s1070428002120023

文献信息

• Acyl iodides in organic synthesis: VIII. Reactions with amino acids
  作者：M. G. Voronkov、L. I. Belousova、A. A. Trukhina、N. L. Vlasova

  DOI：10.1134/s1070428002120023

  日期：2006.2

  Reactions of acyl iodides RCOI (R=Me, Ph) with glycine, beta-alanine, and gamma-aminobutyric acid were investigated. The reaction proceeded easily at room temperature without solvent involving both functional groups H2N and COOH. The prevalence of one of the reaction directions depends on the acidity of the amino acid. The more acidic glycine (pK(a) 2.4) reacts with RCOI affording mainly N-acylated product, whereas beta-alanine (pK(a) 3.60) and especially gamma-aminobutyric acid (pK(a) 4.06) are predominantly involved into exchange iodination furnishing the corresponding aminoacyl iodides.