N-Butyl-6-heptenamide | 134852-92-9

• 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-Butyl-6-heptenamide
• 英文别名: heptene-6-carboxylic acid N-butylamide；N-butylhept-6-enamide
• CAS: 134852-92-9
• 化学式: C₁₁H₂₁NO
• 分子量: 183.294
• InChiKey: XGELHIKEHFMQLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-Butyl-6-heptenamide 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 12.0h， 生成 N-butyl-N-hept-6-enoylcarbamoyl chloride
  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
• 作为产物：
  描述：

  2-butyl-3,3-(1'-methyl)pentamethyleneoxaziridine 、 铁(2+)硫酸酯 生成 N-Butyl-6-heptenamide
  参考文献：
  名称：

  SHMITTS, E.;KAPUSTINA, I. I.;ZONNESHAJN, X.;NIKISHIN, G. I., IZV. AN CCCP. CEP. XIM.,(1991) N, S. 954-958

  摘要：

  DOI：

文献信息

• 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.
• Cleavage of spirooxaziridines by the action of ferrous sulfate
  作者：E. Schmitz、N. I. Kapustina、H. Sonnestein、G. I. Nikishin

  DOI：10.1007/bf00958590

  日期：1991.4

  The reaction of 2-butyl-3,3-(1'-heptyl)tetramethyleneoxaziridine with ferrous sulfate gave the N-butylamides of E- and Z-4-dodecenecarboxylic and E- and Z-5-dodecenecarboxylic acids in approximately 1:1 ratio. Analogously, 2-butyl-3,3-(1'-alkyl)pentamethyleneoxaziridines gave the N-butylamides of the corresponding E- and Z-unsaturated carboxylic acids.
• SHMITTS, E.;KAPUSTINA, I. I.;ZONNESHAJN, X.;NIKISHIN, G. I., IZV. AN CCCP. CEP. XIM.,(1991) N, S. 954-958
  作者：SHMITTS, E.、KAPUSTINA, I. I.、ZONNESHAJN, X.、NIKISHIN, G. I.

  DOI：——

  日期：——
• 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.