1-methyl-1-<2-(4-p-nitrophenyl)ethyl>azepanium iodide

• 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: 1-methyl-1-<2-(4-p-nitrophenyl)ethyl>azepanium iodide
• 英文别名: 1-Methyl-1-[2-(4-nitrophenyl)ethyl]azepan-1-ium;iodide
• 化学式: C₁₅H₂₃N₂O₂*I
• 分子量: 390.264
• InChiKey: MMXRPWDLPLDGOV-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.16
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-methyl-1-<2-(4-p-nitrophenyl)ethyl>azepanium iodide 在 氢氧化钾 作用下， 以 水 为溶剂， 生成 4-硝基苯乙烯 、 1-Methylazepan-1-ium;iodide
  参考文献：
  名称：

  Study on the Effect of the Structure of the Leaving Group in the E1cb Mechanism of Base-Promoted .beta.-Elimination Reactions from N-[2-(p-Nitrophenyl)ethyl]alkylammonium Ions

  摘要：

  Studies of acid-base catalysis, H/D exchange, and solvent isotope effect on the P-elimination reactions with formation of p-nitrostyrene in acetohydroxamate/acetohydroxamic acid buffers at pH 9.05, H2O, mu = 1 M KCl, 25 degrees C, from N-[2-(p-nitrophenyl)ethyl]alkylammonium ions with different leaving groups, such as N-methylpyrrolidine 1,N-ethylpyrrolidine 2,N-isopropylpyrrolidine 3, N-methylpiperidine 4,N-isopropylpiperidine 5, and N-methylazepane 6, show a change from a partially reversible E1cb mechanism with 1, 2, and 4 to an irreversible E1cb mechanism with 3, 5, and 6. The change in the rate-determining step is related to the increased steric requirement of the leaving group. A steric acceleration from the carbanion intermediate to product step is proposed.

  DOI：

  10.1021/jo00131a011
• 作为产物：
  描述：

  4-硝基苯乙基溴 以 乙腈 为溶剂， 反应 12.0h， 生成 1-methyl-1-<2-(4-p-nitrophenyl)ethyl>azepanium iodide
  参考文献：
  名称：

  Study on the Effect of the Structure of the Leaving Group in the E1cb Mechanism of Base-Promoted .beta.-Elimination Reactions from N-[2-(p-Nitrophenyl)ethyl]alkylammonium Ions

  摘要：

  Studies of acid-base catalysis, H/D exchange, and solvent isotope effect on the P-elimination reactions with formation of p-nitrostyrene in acetohydroxamate/acetohydroxamic acid buffers at pH 9.05, H2O, mu = 1 M KCl, 25 degrees C, from N-[2-(p-nitrophenyl)ethyl]alkylammonium ions with different leaving groups, such as N-methylpyrrolidine 1,N-ethylpyrrolidine 2,N-isopropylpyrrolidine 3, N-methylpiperidine 4,N-isopropylpiperidine 5, and N-methylazepane 6, show a change from a partially reversible E1cb mechanism with 1, 2, and 4 to an irreversible E1cb mechanism with 3, 5, and 6. The change in the rate-determining step is related to the increased steric requirement of the leaving group. A steric acceleration from the carbanion intermediate to product step is proposed.

  DOI：

  10.1021/jo00131a011

文献信息

• Study on the Effect of the Structure of the Leaving Group in the E1cb Mechanism of Base-Promoted .beta.-Elimination Reactions from N-[2-(p-Nitrophenyl)ethyl]alkylammonium Ions
  作者：S. Alunni、P. Tijskens

  DOI：10.1021/jo00131a011

  日期：1995.12

  Studies of acid-base catalysis, H/D exchange, and solvent isotope effect on the P-elimination reactions with formation of p-nitrostyrene in acetohydroxamate/acetohydroxamic acid buffers at pH 9.05, H2O, mu = 1 M KCl, 25 degrees C, from N-[2-(p-nitrophenyl)ethyl]alkylammonium ions with different leaving groups, such as N-methylpyrrolidine 1,N-ethylpyrrolidine 2,N-isopropylpyrrolidine 3, N-methylpiperidine 4,N-isopropylpiperidine 5, and N-methylazepane 6, show a change from a partially reversible E1cb mechanism with 1, 2, and 4 to an irreversible E1cb mechanism with 3, 5, and 6. The change in the rate-determining step is related to the increased steric requirement of the leaving group. A steric acceleration from the carbanion intermediate to product step is proposed.