N-(E-2-methylpent-2-enoyl)trimethylacetamide | 848872-72-0

• 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-(E-2-methylpent-2-enoyl)trimethylacetamide
• 英文别名: (E)-N-(2,2-dimethylpropanoyl)-2-methylpent-2-enamide
• CAS: 848872-72-0
• 化学式: C₁₁H₁₉NO₂
• 分子量: 197.277
• InChiKey: AQRDLJHXPFKINQ-BQYQJAHWSA-N

物化性质

• 熔点：
  101-102 °C
• 沸点：
  308.2±15.0 °C(Predicted)
• 密度：
  0.954±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-甲基-C-苯基硝酮 、 N-(E-2-methylpent-2-enoyl)trimethylacetamide 在 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (+/-)-5-ethyl-2,4-dimethyl-3-phenylisoxazolidine-4-carboxylic acid (2,2-dimethylpropionyl)amide 、 5-ethyl-2,4-dimethyl-3-phenylisoxazolidine-4-carboxylic acid (2,2-dimethylpropionyl)amide
  参考文献：
  名称：

  Enantioselective Cycloadditions with α,β-Disubstituted Acrylimides

  摘要：

  The use of N-H imide templates provides a solution to the problem of rotamer control in Lewis acid catalyzed reactions of α,β-disubstituted acryloyl imides. Reactions proceed through the s-cis rotamer and with improved reactivity because A(1,3) strain is avoided. Enantioselective nitrone, nitrile oxide, and Diels-Alder cycloadditions demonstrate the principle.

  DOI：

  10.1021/ol050599d
• 作为产物：
  描述：

  草莓酸 在 草酰氯 、 sodium hydride 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.75h， 生成 N-(E-2-methylpent-2-enoyl)trimethylacetamide
  参考文献：
  名称：

  Enantioselective Radical Addition/Trapping Reactions with α,β-Disubstituted Unsaturated Imides. Synthesis of anti-Propionate Aldols

  摘要：

  This manuscript describes a highly diastereo- and enantioselective intermolecular radical addition/hydrogen atom transfer to alpha,beta-disubstituted enoates. Additionally, we show that anti-propionate aldol-like products can be easily prepared from alpha-methyl-beta-acyloxyenoates in good yields and high diastereo- and enantioselectivities.

  DOI：

  10.1021/ja043371e

文献信息

• Enantioselective Radical Addition/Trapping Reactions with α,β-Disubstituted Unsaturated Imides. Synthesis of <i>a</i><i>nti</i>-Propionate Aldols
  作者：Mukund P. Sibi、Goran Petrovic、Jake Zimmerman

  DOI：10.1021/ja043371e

  日期：2005.3.1

  This manuscript describes a highly diastereo- and enantioselective intermolecular radical addition/hydrogen atom transfer to alpha,beta-disubstituted enoates. Additionally, we show that anti-propionate aldol-like products can be easily prepared from alpha-methyl-beta-acyloxyenoates in good yields and high diastereo- and enantioselectivities.
• Enantioselective Cycloadditions with α,β-Disubstituted Acrylimides
  作者：Mukund P. Sibi、Zhihua Ma、Kennosuke Itoh、Prabagaran Narayanasamy、Craig P. Jasperse

  DOI：10.1021/ol050599d

  日期：2005.6.9

  The use of N-H imide templates provides a solution to the problem of rotamer control in Lewis acid catalyzed reactions of α,β-disubstituted acryloyl imides. Reactions proceed through the s-cis rotamer and with improved reactivity because A(1,3) strain is avoided. Enantioselective nitrone, nitrile oxide, and Diels-Alder cycloadditions demonstrate the principle.