N-Butyl-5-<(phenylseleno)methyl>-2-pyrrolidinone | 134612-87-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-Butyl-5-<(phenylseleno)methyl>-2-pyrrolidinone
• 英文别名: 1-Butyl-5-(phenylselanylmethyl)pyrrolidin-2-one
• CAS: 134612-87-6
• 化学式: C₁₅H₂₁NOSe
• 分子量: 310.298
• InChiKey: WLWWDTKELIKLHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-butylpent-4-enimidoyl chloride 以 乙醚 、 苯 为溶剂， 反应 26.0h， 生成 N-Butyl-5-<(phenylseleno)methyl>-2-pyrrolidinone
  参考文献：
  名称：

  酰胺基自由基的轻松生产和环化

  摘要：

  酰胺通过亚氨酰氯转化为N-羟基吡啶-2-硫酮亚氨酸酯，它们是酰胺基的前体。含有δ，γ-不饱和基团的酰胺基以5 exo的方式环化。

  DOI：

  10.1016/s0040-4039(00)74480-7

文献信息

• Chemistry of amidyl radicals produced from N-hydroxypyridine-2-thione imidate esters
  作者：John L. Esker、Martin Newcomb

  DOI：10.1021/jo00070a033

  日期：1993.8

  The title radical precursors were prepared from secondary amides by reaction of the amide with phosgene to give an imidoyl chloride followed by reaction with the sodium salt of N-hydroxypyridine-2-thione. Visible light initiated reactions of these precursors gave amidyl radicals 2 which could react with their precursors to give N-(2-pyridylthio) amides or with t-BuSH to give the parent amide. Radicals 2 containing delta,epsilon-unsaturation on the acyl or alkyl chain cyclized in a 5-exo fashion to give ultimately gamma-lactams and N-acylpyrrolidines, respectively. Tandem 5-exo cyclizations of the N-allyl-4-pentenamidyl radical gave pyrrolizidinone products, and a tandem 5-exo/6-endo reaction sequence of the N-(4-pentenyl)benzamidyl radical gave, ultimately, 3,4-benzoindolizidinone. Several relative rate constants for cyclization and trapping of the amidyl radicals and for intramolecular reactions and trapping of the carbon-centered radicals formed by amidyl radical cyclizations were determined, and these values can be employed in synthetic planning.
• Facile production and cyclizations of amidyl radicals
  作者：Martin Newcomb、John L. Esker

  DOI：10.1016/s0040-4039(00)74480-7

  日期：1991.2

  Amides were converted via imidoyl chlorides into N-hydroxypyridine-2-thione imidate esters that were precursors for amidyl radicals; amidyl radicals containing δ,ϵ-unsaturated cyclized in a 5-exo fashion.

  酰胺通过亚氨酰氯转化为N-羟基吡啶-2-硫酮亚氨酸酯，它们是酰胺基的前体。含有δ，γ-不饱和基团的酰胺基以5 exo的方式环化。