1-<(N-Acetyl-N-methylcarbamoyl)oxy>-2(1H)-pyridinethione | 144809-63-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-<(N-Acetyl-N-methylcarbamoyl)oxy>-2(1H)-pyridinethione
• 英文别名: (2-sulfanylidenepyridin-1-yl) N-acetyl-N-methylcarbamate
• CAS: 144809-63-2
• 化学式: C₉H₁₀N₂O₃S
• 分子量: 226.256
• InChiKey: OWIKBCYVJKJZGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  81.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-<(N-Acetyl-N-methylcarbamoyl)oxy>-2(1H)-pyridinethione 以75%的产率得到
  参考文献：
  名称：

  Esker John L., Newcomb Martin, J. Org. Chem, 59 (1994) N 10, S 2779-2786

  摘要：

  DOI：
• 作为产物：
  描述：

  N-Acetyl-N-methylcarbamoyl chloride 、 2-mercaptopyridine-1-oxide sodium salt 以 苯 为溶剂， 反应 1.5h， 生成 1-<(N-Acetyl-N-methylcarbamoyl)oxy>-2(1H)-pyridinethione
  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

• 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.
• 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.
• 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：——