2-methyl-1-phenyl-1-propylbut-3-enylamine

• 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: 2-methyl-1-phenyl-1-propylbut-3-enylamine
• 英文别名: (3S,4S)-3-methyl-4-phenylhept-1-en-4-amine
• 化学式: C₁₄H₂₁N
• 分子量: 203.327
• InChiKey: YZXGIPYUUJIKLJ-JSGCOSHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯丁酮 在 盐酸 、 samarium diiodide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.0h， 生成 2-methyl-1-phenyl-1-propylbut-3-enylamine
  参考文献：
  名称：

  Stereoselective Synthesis of Both syn- and anti-N-tert-Alkylamines Using Highly Stereospecific Crotylation of Ketone-Derived Acylhydrazones with Crotyltrichlorosilanes

  摘要：

  Crotyltrichlorosilanes reacted with ketone-derived N-benzoylhydrazones in DMF without any catalyst. This is the first example of highly stereospecific crotylation of ketimine analogues leading to both syn- and anti-N'-tert-alkyl-N-benzoylhydrazines. Different reactivities between (Z)- and (E)-crotylsilanes in terms of yields and selectivities were observed. A kinetic study with both geometrically pure (Z)- and (E)-crotylsilanes was performed. These reactions are most likely to proceed via a cyclic chairlike transition state where the aromatic group of hydrazones takes an axial position. Both diastereomers of allylation products can be converted to the corresponding alpha,alpha-disubstituted homoallylic amines without epimerization.

  DOI：

  10.1021/jo0258599

文献信息

• Stereoselective Synthesis of Both <i>syn- </i>and <i>anti</i>-<i>N</i>-<i>tert</i>-Alkylamines Using Highly Stereospecific Crotylation of Ketone-Derived Acylhydrazones with Crotyltrichlorosilanes
  作者：Chikako Ogawa、Masaharu Sugiura、Shū Kobayashi

  DOI：10.1021/jo0258599

  日期：2002.7.1

  Crotyltrichlorosilanes reacted with ketone-derived N-benzoylhydrazones in DMF without any catalyst. This is the first example of highly stereospecific crotylation of ketimine analogues leading to both syn- and anti-N'-tert-alkyl-N-benzoylhydrazines. Different reactivities between (Z)- and (E)-crotylsilanes in terms of yields and selectivities were observed. A kinetic study with both geometrically pure (Z)- and (E)-crotylsilanes was performed. These reactions are most likely to proceed via a cyclic chairlike transition state where the aromatic group of hydrazones takes an axial position. Both diastereomers of allylation products can be converted to the corresponding alpha,alpha-disubstituted homoallylic amines without epimerization.