N,N-dimethyl-3-methyl-3-butenamide | 19435-60-0

• 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,N-dimethyl-3-methyl-3-butenamide
• 英文别名: 3-Methyl-buten-(3)-saeure-dimethylamid；3.N.N-Trimethyl-but-3-ensaeure-amid；3-methyl-but-3-enoic acid dimethylamide；3-Methyl-but-3-ensaeure-dimethylamid；N,N,3-trimethylbut-3-enamide
• CAS: 19435-60-0
• 化学式: C₇H₁₃NO
• 分子量: 127.186
• InChiKey: XAEVKGJHYJCCGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N.N-二甲基异丁烯酰胺 1000.0 ℃ 、0.2 Pa 条件下， 以100%的产率得到N,N-dimethyl-3-methyl-3-butenamide
  参考文献：
  名称：

  Cyclisation at very high temperature. Thermal transformations of N-alkyl and N, N-dialkyl amides of α,β-unsaturated acids into mono- and bicyclic heterocycles under FVT conditions

  摘要：

  Cyclisations of N-alkyl and N,N-dialkyl cinnamic amides to the corresponding pyrrolidin-2-ones under the conditions of flash vacuum thermolysis (FVT), are described. It was found that these reactions proceed at 950-1000 degrees C affording in various yields the mixtures of isomeric mono and bicyclic gamma-lactams, which were separated chromatographically and analysed by means of NMR spectroscopy. Two alternative mechanisms for the title process are proposed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.011

文献信息

• Palladium-Catalyzed Conversion of Benzylic and Allylic Halides into α-Aryl and β,γ-Unsaturated Tertiary Amides by the Use of a Carbamoylsilane
  作者：Robert F. Cunico、Rajesh K. Pandey

  DOI：10.1021/jo0512406

  日期：2005.10.1

  Treatment of allylic and benzylic halides with N,N-dimethylcarbamoyl(trimethyl)silane in the presence of tetrakis(triphenylphosphine)palladium(0) affords tertiary amides, which arise from the replacement of the halogen by the N,N-dimethylcarbamoyl group.

  在四（三苯基膦）钯（0）​​存在下，用N，N-二甲基氨基甲酰基（三甲基）硅烷处理烯丙基和苄基卤化物可得到叔酰胺，这是由N，N-二甲基氨基甲酰基取代卤素而产生的。
• γ-Silylated α,β-unsaturated amides — Preparation by [1,5]-sigmatropic rearrangement and use as masked dienolate equivalents in carbonyl condensations
  作者：James R. Green、Babajide I. Alo、Marek Majewski、Victor Snieckus

  DOI：10.1139/v09-054

  日期：2009.6

  The reaction of lithium dienolates derived from N,N-dialkylsenecioamides (1a–1c) with triorganosilyl electrophiles occurs initially at the oxygen atom predominantly, and is followed by an O → C silicon migration to afford the γ-silylated senecioamides (4a–4h). The γ-silylated senecioamide Z-4a undergoes fluoride-ion-mediated condensations with aromatic aldehydes to give kinetic α-(6) and thermodynamic γ-(5) condensation product patterns comparable to lithium dienolates. The TiCl₄-mediated reactions with aldehydes gives α-products (6) in a highly syn-selective manner. Possible transition-state models for the syn-selective condensations are discussed and a chair-like transition state featuring bidentate coordination to titanium (11) is proposed.

  由 N,N-二烷基烯酰胺（1a-1c）衍生的二元醇锂与三有机硅亲电体的反应最初主要发生在氧原子上，随后发生 O → C 硅迁移，生成γ-硅烷基烯酰胺（4a-4h）。γ-硅烷化的番泻酰胺 Z-4a 与芳香醛发生氟离子介导的缩合反应，得到与二烯酸锂相似的动力学α-(6) 和热力学γ-(5) 缩合产物模式。TiCl4 介导的与醛的反应以高度合成选择性的方式产生了 α 产物 (6)。讨论了合成选择性缩合的可能过渡态模型，并提出了以钛的双齿配位为特征的椅状过渡态 (11)。
• The Decarboxylation of α,β-Unsaturated Malonic Acid Derivatives via β,γ-Unsaturated Intermediates. II. The Effect of α-Substituents upon Product Composition and Rate
  作者：Elias J. Corey

  DOI：10.1021/ja01101a046

  日期：1953.3
• Metalated unsaturated amides. Regio- and stereoselective .gamma.-alkylation
  作者：M. Majewski、G. B. Mpango、M. T. Thomas、A. Wu、V. Snieckus

  DOI：10.1021/jo00323a012

  日期：1981.5
• Dietrich,W. et al., Zeitschrift fur Chemie, 1975, vol. 15, p. 266 - 267
  作者：Dietrich,W. et al.

  DOI：——

  日期：——