N-[(E)-1-(4-methylphenyl)propylideneamino]benzamide

• 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-[(E)-1-(4-methylphenyl)propylideneamino]benzamide
• 化学式: C₁₇H₁₈N₂O
• 分子量: 266.343
• InChiKey: NGNYUXQWQYQSGT-FBMGVBCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-crotyltrichlorosilane 、 N-[(E)-1-(4-methylphenyl)propylideneamino]benzamide 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 N'-(1-ethyl-2-methyl-1-p-tolylbut-3-enyl)benzohydrazide 、 N'-(1-ethyl-2-methyl-1-p-tolylbut-3-enyl)benzohydrazide
  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
• 作为产物：
  描述：

  对甲基苯丙酮 、 苯甲酰肼 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 N-[(E)-1-(4-methylphenyl)propylideneamino]benzamide
  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

• HUFF, A. M.;HALL, H. L.;SMITH, M. J.;OGRADY, SH. A.;WATERS, F. C.;FENGL, +, J. HETEROCYCL. CHEM., 1985, 22, N 2, 501-504
  作者：HUFF, A. M.、HALL, H. L.、SMITH, M. J.、OGRADY, SH. A.、WATERS, F. C.、FENGL, +

  DOI：——

  日期：——
• 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.