N-benzyl-2-bromo-N-(cyclooct-1-enyl)-2-methylpropionamide | 256642-06-5

• 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-(cyclooct-1-enyl)-2-methylpropionamide
• CAS: 256642-06-5
• 化学式: C₁₉H₂₆BrNO
• 分子量: 364.326
• InChiKey: FCNMKORGSCHDJY-UHFFFAOYSA-N

物化性质

• 沸点：
  474.9±44.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-benzyl-2-bromo-N-(cyclooct-1-enyl)-2-methylpropionamide 在 钾硼氢 、 Cu(tris(2-pyridylmethyl)amine)SO₄*5H₂O 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以11%的产率得到1-benzyl-3,3-dimethyl-hexahydro-cycloocta[b]pyrrolidin-2-one
  参考文献：
  名称：

  Atom-Transfer Cyclization with CuSO₄/KBH₄: A Formal “Activators Generated by Electron Transfer” Process Also Applicable to Atom-Transfer Polymerization

  摘要：

  The 4-exo and 5-exo-trig atom-transfer cyclizations of 1, 8a-e, 9, 12, and 13 can be mediated with as little as 0.05 mol % of Cu(TPMA)SO4 center dot 5H(2)O in the presence of 2.5 mol % of borohydride salts in 10 min at room temperature in air. This formal "activators generated by electron transfer" (AGET) procedure utilizes a cheap and oxidatively stable copper source (CuSO4 center dot 5H(2)O) and can be carried out in environmentally benign solvents (EtOH). It is possible to alter the product distribution in the 5-endo radical-polar crossover reactions of 10a,b and 11 by tailoring the amount of borohydride. Cyclization onto alkynes 14 and 15 is also possible in only 20 min. Controlled radical polymerization of styrene, with increased rates over conventional atom-transfer radical polymerization (ATRP), can be carried out in a controlled fashion (Mn, PDI) using either CuBr or CuSO4 center dot 5H(2)O and Bu4NBH4.

  DOI：

  10.1021/jo301429a
• 作为产物：
  描述：

  2-溴-2-甲基丙酰溴 、 N-cyclooctylidene(phenyl)methanamine 在 N,N-二乙基苯胺 作用下， 以 甲苯 为溶剂， 以95%的产率得到N-benzyl-2-bromo-N-(cyclooct-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