N-methyl-N-[2-(1-methyl-1-trimethylsilanyloxyethyl)phenyl]acrylamide | 202276-25-3

• 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-[2-(1-methyl-1-trimethylsilanyloxyethyl)phenyl]acrylamide
• CAS: 202276-25-3
• 化学式: C₁₆H₂₅NO₂Si
• 分子量: 291.466
• InChiKey: GZNVWACEHNCZHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-methyl-N-[2-(1-methyl-1-trimethylsilanyloxyethyl)phenyl]acrylamide 、 tert-butyl nitrile oxide 在 TEA 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 3-tert-butyl-4,5-dihydro-isoxazole-5-carboxylic acid methyl-[2-(1-methyl-1-trimethylsilanyloxyethyl)-phenyl]amide 、 3-tert-butyl-4,5-dihydro-isoxazole-5-carboxylic acid methyl-[2-(1-methyl-1-trimethylsilanyloxyethyl)-phenyl]amide
  参考文献：
  名称：

  Rotational features of carbon-nitrogen bonds in axially chiral o-tert-butyl anilides and related molecules. Potential substrates for the ‘prochiral auxiliary’ approach to asymmetric synthesis

  摘要：

  A new strategy for asymmetric induction termed the 'prochiral auxiliary' approach is introduced. Reactions of acylating agents with prochiral N-methyl-o-tert-butyl aniline provide anilides that are axially chiral by virtue of restricted rotation about the N-Ar bond, Rotamer populations about the amide bond (E/Z) were studied by H-1 NMR. Several pairs of enantiomeric o-tert-butyl anilides were separated by chiral chromatography and barriers about the N-Ar bond were measured by thermal racemization. Related o-(1-(trialkylsilyloxy)-1-methylethyl) anilides were also studied. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00599-5
• 作为产物：
  描述：

  2-(methylamino) α-dimethylbenzyl alcohol 在 吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 N-methyl-N-[2-(1-methyl-1-trimethylsilanyloxyethyl)phenyl]acrylamide
  参考文献：
  名称：

  Rotational features of carbon-nitrogen bonds in axially chiral o-tert-butyl anilides and related molecules. Potential substrates for the ‘prochiral auxiliary’ approach to asymmetric synthesis

  摘要：

  A new strategy for asymmetric induction termed the 'prochiral auxiliary' approach is introduced. Reactions of acylating agents with prochiral N-methyl-o-tert-butyl aniline provide anilides that are axially chiral by virtue of restricted rotation about the N-Ar bond, Rotamer populations about the amide bond (E/Z) were studied by H-1 NMR. Several pairs of enantiomeric o-tert-butyl anilides were separated by chiral chromatography and barriers about the N-Ar bond were measured by thermal racemization. Related o-(1-(trialkylsilyloxy)-1-methylethyl) anilides were also studied. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00599-5