N-Methyl-N-(trimethylsilyl)benzamide | 23728-68-9

• 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-Methyl-N-(trimethylsilyl)benzamide
• 英文别名: N-methyl-N-trimethylsilanyl-benzamide；N-Methyl-N-trimethylsilyl-benzamid；N-Methyl-N-trimethylsilylbenzamid；N-Trimethylsilyl-N-methylbenzamid；N-methyl-N-(trimethyl silyl)benzamide；N-methyl-N-trimethylsilylbenzamide
• CAS: 23728-68-9
• 化学式: C₁₁H₁₇NOSi
• 分子量: 207.348
• InChiKey: TWPWJLWWVYRVKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-Methyl-N-(trimethylsilyl)benzamide 在 三氯化磷 作用下， 反应 12.0h， 以52%的产率得到tris(methylbenzoylamino)phosphine
  参考文献：
  名称：

  Malenko, D. M.; Nesterova, L. I.; Luk'yanenko, S. N., Russian Journal of General Chemistry, 1993, vol. 63, # 7.2, p. 1171 - 1172

  摘要：

  DOI：
• 作为产物：
  描述：

  七甲基二硅氮烷 、 N-((tert-butylimino)methylene)benzamide 生成 N-Methyl-N-(trimethylsilyl)benzamide
  参考文献：
  名称：

  IV族有机金属化合物的反应：XXVII。苯甲酰基-叔丁基碳二亚胺与IV族三甲基金属甲胺的插入反应和三甲基-甲硅烷基-和-γ-叔丁基碳二亚胺的制备

  摘要：

  苯甲酰基叔butylcarbodiimide的与我的插入3 MNMe 2（M = Si，Ge和Sn）的或（ME 3 M）2 NME（M = Si和Sn）进行说明。的11个加合物由organosilyl-和organogermyl-胺pyrolyses得到相应的我3 MNCNCMe 3通过消除（M = Si和Ge）Ñ，Ñ二取代benzarnides。

  DOI：

  10.1016/s0022-328x(00)89738-7

文献信息

• Synthesis of arylimines from N-silylamides amd aryllithium compounds
  作者：Ben L. Feringa、Johan F.G.A. Jansen

  DOI：10.1016/s0040-4039(00)85517-3

  日期：1986.1

  Various arylimines were synthesized by the addition of N-silylated-N-alkyl-or N-aryl-amides to aryllithium compounds.

  通过将N-甲硅烷基化的-N-烷基-或N-芳基-酰胺加到芳基锂化合物上来合成各种芳胺。
• Schorr, Manfred; Schmitt, Wilfried, Phosphorus, Sulfur and Silicon and the Related Elements, 1992, vol. 68, # 1-4, p. 25 - 36
  作者：Schorr, Manfred、Schmitt, Wilfried

  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.
• Fedotov,N.S. et al., Journal of general chemistry of the USSR, 1972, vol. 42, p. 348 - 353
  作者：Fedotov,N.S. et al.

  DOI：——

  日期：——
• 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.