N-Butyl-5-<(2'-pyridylthio)methyl>-2-pyrrolidinone | 134612-86-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N-Butyl-5-<(2'-pyridylthio)methyl>-2-pyrrolidinone
• 英文别名: N-Butyl-5-((2-pyridylthio)methyl)-2-pyrrolidinone；1-Butyl-5-(pyridin-2-ylsulfanylmethyl)pyrrolidin-2-one
• CAS: 134612-86-5
• 化学式: C₁₄H₂₀N₂OS
• 分子量: 264.392
• InChiKey: YFVPLFZOEGUNMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  58.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-butyl-N-pent-4-enoylcarbamoyl chloride 以 乙腈 、 苯 为溶剂， 反应 1.5h， 生成 N-Butyl-5-<(2'-pyridylthio)methyl>-2-pyrrolidinone
  参考文献：
  名称：

  N-Acyl-N-alkylcarbamoyloxy radicals: Entries to amidyl radicals by decar☐ylation and to α-amide radicals by radical translocation

  摘要：

  N'-Acyl-N-hydroxypyridine-2-thione carbamates react in radical chain reactions to give the title radicals which can decarboxylate or react by intramolecular hydrogen atom transfer; the competing reaction pathways are controlled by the structure of the alkyl group and the conformation of the precursor which can be influenced by addition of a Lewis acid.

  DOI：

  10.1016/s0040-4039(00)61087-0

文献信息

• 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。
• N-Acyl-N-alkylcarbamoyloxy radicals: Entries to amidyl radicals by decar☐ylation and to α-amide radicals by radical translocation
  作者：John L. Esker、Martin Newcomb

  DOI：10.1016/s0040-4039(00)61087-0

  日期：1992.9

  N'-Acyl-N-hydroxypyridine-2-thione carbamates react in radical chain reactions to give the title radicals which can decarboxylate or react by intramolecular hydrogen atom transfer; the competing reaction pathways are controlled by the structure of the alkyl group and the conformation of the precursor which can be influenced by addition of a Lewis acid.
• 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.
• Esker John L., Newcomb Martin, J. Org. Chem, 59 (1994) N 10, S 2779-2786
  作者：Esker John L., Newcomb Martin

  DOI：——

  日期：——
• Multiple Reaction Channels of (N-Acyl-N-alkylcarbamoyl)oxyl Radicals from N-Acyl PTOC Carbamates
  作者：John L. Esker、Martin Newcomb

  DOI：10.1021/jo00089a023

  日期：1994.5

  N-Acyl-N-alkyl-N'-hydroxypyridine-2-thione carbamates (N-acyl PTOC carbamates) 1 are prepared in good to excellent yield by reactions of N-acylcarbamoyl chlorides with N-hydroxypyridine-2-thione sodium salt. Methods for production of the requisite carbamoyl chlorides by reaction of a secondary amide with trimethylsilyl triflate followed by treatment with phosgene were optimized. Precursors 1 react in radical chain reactions to give the title radicals (2) that can further react by several pathways. Decarboxylations of radicals 2 give amidyl radicals, and this method is excellent for production of acetamidyl radicals and in particular the N-methylacetarnidyl radical which is difficult to prepare by other routes. 5-Exo cyclizations of amidyl radicals produced by decarboxylation of 2 give, ultimately, lactams and N-acylpyrrolidines. 1,5-Hydrogen transfer reactions of 2 to give alpha-amide radicals compete with decarboxylation; cyclization of an alpha-amide radical thus formed also is reported. The Lewis acid MgBr2 can reduce the 1,5-hydrogen atom transfer reaction apparently by a chelation effect on the precursor that leads to production of radical 2 in a conformation unfavorable for hydrogen atom transfer. By appropriate experimental design, radicals 2 often can be directed toward one desired reaction, and several relative rate constants for reactions of 2 necessary for such design were determined in this work.