benzyl-methoxycarbonylmethyl-dimethyl-ammonium; bromide | 84555-08-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl-methoxycarbonylmethyl-dimethyl-ammonium; bromide
• 英文别名: Benzyl-methoxycarbonylmethyl-dimethyl-ammonium; Bromid；Carbmethoxymethyl-dimethylbenzylammonium bromide；benzyl-(2-methoxy-2-oxoethyl)-dimethylazanium;bromide
• CAS: 84555-08-8
• 化学式: Br*C₁₂H₁₈NO₂
• 分子量: 288.184
• InChiKey: GBKZVWOAVSJRQO-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.56
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl-methoxycarbonylmethyl-dimethyl-ammonium; bromide 在 potassium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以65%的产率得到methyl N,N-dimethylphenylalaninate
  参考文献：
  名称：

  Controlling Selectivity by Controlling the Path of Trajectories

  摘要：

  Consideration of the role of dynamic trajectories in [1,2]- and [2,3]-sigmatropic rearrangements suggests a counterintuitive approach to controlling the selectivity. In our hypothesis, [2,3] selectivity can be promoted by reaction conditions that thermodynamically disfavor the [2,3] rearrangement step and thereby make the transition state later. The application of this idea has led to a successful prescription for dictating the selectivity in Stevens/Sommelet-Hauser rearrangements of ammonium ylides. A combination of kinetic isotope effects, crossover experiments, and computational dynamic trajectories support the idea that the selectivity is controlled through control of the path of trajectories.

  DOI：

  10.1021/jacs.5b08635
• 作为产物：
  描述：

  N,N-二甲基甘氨酸甲酯 、 溴甲苯 以 乙醚 为溶剂， 反应 12.0h， 以85%的产率得到benzyl-methoxycarbonylmethyl-dimethyl-ammonium; bromide
  参考文献：
  名称：

  Controlling Selectivity by Controlling the Path of Trajectories

  摘要：

  Consideration of the role of dynamic trajectories in [1,2]- and [2,3]-sigmatropic rearrangements suggests a counterintuitive approach to controlling the selectivity. In our hypothesis, [2,3] selectivity can be promoted by reaction conditions that thermodynamically disfavor the [2,3] rearrangement step and thereby make the transition state later. The application of this idea has led to a successful prescription for dictating the selectivity in Stevens/Sommelet-Hauser rearrangements of ammonium ylides. A combination of kinetic isotope effects, crossover experiments, and computational dynamic trajectories support the idea that the selectivity is controlled through control of the path of trajectories.

  DOI：

  10.1021/jacs.5b08635

文献信息

• THE BASIS FOR THE PHYSIOLOGICAL ACTIVITY OF -ONIUM COMPOUNDS. IX. DERIVATIVES OF HOMOLOGS OF BETAINE¹
  作者：R. R. Renshaw、M. E. McGreal

  DOI：10.1021/ja01343a029

  日期：1932.4
• Controlling Selectivity by Controlling the Path of Trajectories
  作者：Bibaswan Biswas、Daniel A. Singleton

  DOI：10.1021/jacs.5b08635

  日期：2015.11.18

  Consideration of the role of dynamic trajectories in [1,2]- and [2,3]-sigmatropic rearrangements suggests a counterintuitive approach to controlling the selectivity. In our hypothesis, [2,3] selectivity can be promoted by reaction conditions that thermodynamically disfavor the [2,3] rearrangement step and thereby make the transition state later. The application of this idea has led to a successful prescription for dictating the selectivity in Stevens/Sommelet-Hauser rearrangements of ammonium ylides. A combination of kinetic isotope effects, crossover experiments, and computational dynamic trajectories support the idea that the selectivity is controlled through control of the path of trajectories.