N,N'-dibutyl-2,3-diphenylsuccinic diamide | 51003-40-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: N,N'-dibutyl-2,3-diphenylsuccinic diamide
• 英文别名: N,N'-Dibutyl-2,3-diphenylsuccinamide；N,N'-dibutyl-2,3-diphenylbutanediamide
• CAS: 51003-40-8
• 化学式: C₂₄H₃₂N₂O₂
• 分子量: 380.53
• InChiKey: DHCNEHBNVIDJRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-<(N-Butyl-N-(phenylacetyl)carbamoyl)oxy>-2(1H)-pyridinethione 生成 N,N'-dibutyl-2,3-diphenylsuccinic diamide
  参考文献：
  名称：

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

  摘要：

  DOI：

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.
• Reactions of sulfur diimides with phenyl and chloroketenes
  作者：Toru Minami、Toshio Agawa

  DOI：10.1021/jo00923a010

  日期：1974.5
• 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：——