methyl-[2-(1-methyl-1-trimethylsilanyloxyethyl)phenyl]amine | 202276-13-9

• 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: methyl-[2-(1-methyl-1-trimethylsilanyloxyethyl)phenyl]amine
• 英文别名: N-methyl-2-(2-trimethylsilyloxypropan-2-yl)aniline
• CAS: 202276-13-9
• 化学式: C₁₃H₂₃NOSi
• 分子量: 237.417
• InChiKey: SXSOUDZGBFAFFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  21.26
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  methyl-[2-(1-methyl-1-trimethylsilanyloxyethyl)phenyl]amine 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 N-[2-(1-Hydroxy-1-methyl-ethyl)-phenyl]-N-methyl-3-phenyl-propionamide
  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：

  1-甲基苯唑 在 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 17.0h， 生成 methyl-[2-(1-methyl-1-trimethylsilanyloxyethyl)phenyl]amine
  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