N-benzyl-2-bromo-N-(cyclohept-1-enyl)-2-methylpropionamide | 1152333-55-5

• 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-benzyl-2-bromo-N-(cyclohept-1-enyl)-2-methylpropionamide
• 英文别名: N-benzyl-2-bromo-N-(cyclohepten-1-yl)-2-methylpropanamide
• CAS: 1152333-55-5
• 化学式: C₁₈H₂₄BrNO
• 分子量: 350.299
• InChiKey: GAWAUCZCZFTVPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-溴-2-甲基丙酰溴 、 N-cycloheptylidenebenzylamine 在 N,N-二乙基苯胺 作用下， 以 甲苯 为溶剂， 以71%的产率得到N-benzyl-2-bromo-N-(cyclohept-1-enyl)-2-methylpropionamide
  参考文献：
  名称：

  Bond Rotation Dynamics of N-Cycloalkenyl-N-benzyl α-Haloacetamide Derivatives

  摘要：

  Barriers to rotation of the N-alkenyl bond in a series of N-cycloalkenyl-N-benzyl alpha-haloacetamide derivatives have been measured by variable-temperature NMR experiments. The barriers range from 10 to 18 kcal/mol, depending on ring size and on substituents on the cycloalkene and the amide. The observed trends aid in the design of substituent combinations that provide resolvable enantiomers or diastereomers at ambient temperature. The compounds undergo 4-exo and 5-endo radical cyclizations at rates that may be faster or slower than the estimated rate of N-alkenyl bond rotation in the derived radicals, depending on the substituents.

  DOI：

  10.1021/jo900491w

文献信息

• Bond Rotation Dynamics of <i>N</i>-Cycloalkenyl-<i>N</i>-benzyl α-Haloacetamide Derivatives
  作者：David B. Guthrie、Krishnan Damodaran、Dennis P. Curran、Paul Wilson、Andrew J. Clark

  DOI：10.1021/jo900491w

  日期：2009.6.5

  Barriers to rotation of the N-alkenyl bond in a series of N-cycloalkenyl-N-benzyl alpha-haloacetamide derivatives have been measured by variable-temperature NMR experiments. The barriers range from 10 to 18 kcal/mol, depending on ring size and on substituents on the cycloalkene and the amide. The observed trends aid in the design of substituent combinations that provide resolvable enantiomers or diastereomers at ambient temperature. The compounds undergo 4-exo and 5-endo radical cyclizations at rates that may be faster or slower than the estimated rate of N-alkenyl bond rotation in the derived radicals, depending on the substituents.