N,N-二甲基-1-苯基甲胺氧化物盐酸盐 | 16527-87-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N,N-二甲基-1-苯基甲胺氧化物盐酸盐
• 英文名称: N,N-dimethylbenzylamine N-oxide hydrochloride
• 英文别名: N,N-dimethyl-1-phenylmethanamine oxide;hydrochloride
• CAS: 16527-87-0
• 化学式: C₉H₁₃NO*ClH
• 分子量: 187.669
• InChiKey: NBZNPCPNSRIXMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N,N-二甲基苄胺 在 盐酸 、 双氧水 作用下， 以 甲醇 为溶剂， 以60%的产率得到N,N-二甲基-1-苯基甲胺氧化物盐酸盐
  参考文献：
  名称：

  Structure-Property Relationships in the Basicity and Lipophilicity of Arylalkylamine Oxides

  摘要：

  Homologous N,N-dimethyl-phenylalkylamine oxides and N,N-dimethyl-diphenylalkylamine oxides were prepared. Their basicity and lipophilicity (octan-1-ol/H2O) were compared to those of the parent amines. In contrast to the amines, the basicity of all N,N-dimethyl-arylalkylamine oxides showed very limited pK(a) variations (range 4.65-5.01) with increasing chain length and number of Ph groups. The N-oxides in their neutral form had a log P-N value lower by 2.77 +/- 0.34 (n = 9) units than that of the parent amine. The log P-C of the cationic N,N-dimethyl-diphenylalkylamines was lower than that of their neutral form, with a decrement diff(log PN-C) that increased from 3.25 to 4.21 in the homologous series. Unexpectedly. the decrement diff(log PN-C) for the N-oxides was much smaller than for the tertiary amines, being 0.23 for the aliphatic N,N-dimethyl-pentylamine oxide, 0.47 +/- 0.13 for the phenylalkylamine oxides, and 0.80 +/- 0.07 for the diphenylalkylamine oxides. In fact, the protonated N-oxides had log P-C values that were quite comparable to those of the protonated parent amines. Because of the differences in basicity, the difference in distribution coefficients at physiological pH (log D-7.4) between a tertiary arylalkylamine and its N-oxide was 0.82 +/- 0.66 (n = 9). The pharmacokinetic implication is that N-oxygenation may have a smaller effect on the urinary excretion of tertiary amines than usually assumed.

  DOI：

  10.1002/(sici)1522-2675(19991006)82:10<1630::aid-hlca1630>3.0.co;2-p

文献信息

• Structure-Property Relationships in the Basicity and Lipophilicity of Arylalkylamine Oxides
  作者：Giulia Caron、Giuseppe Ermondi、Donatella Boschi、Pierre-Alain Carrupt、Roberta Fruttero、Bernard Testa、Alberto Gasco

  DOI：10.1002/(sici)1522-2675(19991006)82:10<1630::aid-hlca1630>3.0.co;2-p

  日期：1999.10.6

  Homologous N,N-dimethyl-phenylalkylamine oxides and N,N-dimethyl-diphenylalkylamine oxides were prepared. Their basicity and lipophilicity (octan-1-ol/H2O) were compared to those of the parent amines. In contrast to the amines, the basicity of all N,N-dimethyl-arylalkylamine oxides showed very limited pK(a) variations (range 4.65-5.01) with increasing chain length and number of Ph groups. The N-oxides in their neutral form had a log P-N value lower by 2.77 +/- 0.34 (n = 9) units than that of the parent amine. The log P-C of the cationic N,N-dimethyl-diphenylalkylamines was lower than that of their neutral form, with a decrement diff(log PN-C) that increased from 3.25 to 4.21 in the homologous series. Unexpectedly. the decrement diff(log PN-C) for the N-oxides was much smaller than for the tertiary amines, being 0.23 for the aliphatic N,N-dimethyl-pentylamine oxide, 0.47 +/- 0.13 for the phenylalkylamine oxides, and 0.80 +/- 0.07 for the diphenylalkylamine oxides. In fact, the protonated N-oxides had log P-C values that were quite comparable to those of the protonated parent amines. Because of the differences in basicity, the difference in distribution coefficients at physiological pH (log D-7.4) between a tertiary arylalkylamine and its N-oxide was 0.82 +/- 0.66 (n = 9). The pharmacokinetic implication is that N-oxygenation may have a smaller effect on the urinary excretion of tertiary amines than usually assumed.