N-羟基普萘洛尔 | 84418-31-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: N-羟基普萘洛尔
• 英文名称: N-hydroxypropranolol
• 英文别名: 1-[hydroxy(propan-2-yl)amino]-3-naphthalen-1-yloxypropan-2-ol
• CAS: 84418-31-5
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: VVODPHQSQSFBAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.9
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2922509090

反应信息

• 作为产物：
  描述：

  (RS)-1-bromo-3-(1-naphthyloxy)-2-propanol 、 N-异丙基羟胺 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 N-羟基普萘洛尔
  参考文献：
  名称：

  Derivatives of .beta.-adrenergic antagonists: N-nitrosopropranolol and N-hydroxypropranolol and its aldonitrone

  摘要：

  Potential precursors to chemically reactive species derived from the beta-adrenergic antagonist propranolol were synthesized and tested for mutagenicity in the Ames Salmonella assay. N-Hydroxypropranolol (1), the corresponding aldonitrone, 3-(1-naphthoxy)-2-hydroxypropionaldehyde N-isopropylnitrone (2), and N-nitrosopropranolol (3) were prepared and tested. N-Hydroxypropranolol (1) was obtained by direct alkylation of 3-(1-naphthoxy)-1-bromo-2-propanol with N-isopropylhydroxylamine and isolated as its neutral oxalate or HBr salt. The aldonitrone (2) was obtained by mercuric oxide oxidation of the hydroxylamine. N-Nitrosopropranolol (3) was prepared by treating propranolol with nitrous acid. None of the compounds was mutagenic in the Ames assay with Salmonella typhimurium TA-98 and TA-100 strains, either in the absence or in the presence of the S-9 liver fraction from Arochlor 1254 treated rats. None of the compounds was significantly toxic to the bacteria, except for slight toxicity of the oxalate salt of 1.

  DOI：

  10.1021/jm00357a027

文献信息

• Comparative study on degradation of propranolol and formation of oxidation products by UV/H2O2 and UV/persulfate (PDS)
  作者：Yi Yang、Ying Cao、Jin Jiang、Xinglin Lu、Jun Ma、Suyan Pang、Juan Li、Yongze Liu、Yang Zhou、Chaoting Guan

  DOI：10.1016/j.watres.2018.08.074

  日期：2019.2

  UV/persulfate (UV/PDS) processes are efficient in eliminating propranolol in various waters, but the formation of oxidation products in these processes, as well as the assessment of their toxicity, has not been systematically addressed. In this study, we identified and compared transformation products of propranolol produced by hydroxyl radical (•OH) and sulfate radical (SO4•-). The electrostatic attraction

  普萘洛尔（一种广泛使用的β受体阻滞剂）在废水和地表水中的频繁检测已引起严重关注，因为它对生物体具有不利影响。UV /过氧化氢（UV / H 2 O 2）和UV /过硫酸盐（UV / PDS）工艺可有效消除各种水中的普萘洛尔，但在这些工艺中会形成氧化产物，并评估其毒性，尚未得到系统解决。在这项研究中，我们确定并比较了由羟基（• OH）和硫酸根（SO 4 •-）产生的普萘洛尔的转化产物。静电吸引增强了SO 4 •-之间的反应和•普萘洛尔的质子化形式，而• OH对质子化和中性普萘洛尔种类均显示非选择性。• OH引起的普萘洛尔的羟基化发生在胺基或萘基上，而SO 4 •-则促进了富电子的萘基的氧化。• OH和SO 4 •-进一步氧化产生开环产物。碳酸氢盐和氯化物对心得安的降解没有影响。含CO 3 •和Cl的自由基的产生有利于氧化萘基。费氏弧菌的急性毒性试验表明，SO 4 •-产生的有毒产物比• OH多，而含有CO
• ZHANG, SHOUFANG;POWELL, M. L.;NELSON, W. L.;WIRTH, P. J., J. MED. CHEM., 1983, 26, N 3, 455-458
  作者：ZHANG, SHOUFANG、POWELL, M. L.、NELSON, W. L.、WIRTH, P. J.

  DOI：——

  日期：——
• Derivatives of .beta.-adrenergic antagonists: N-nitrosopropranolol and N-hydroxypropranolol and its aldonitrone
  作者：Shoufang Zhang、Mark L. Powell、Wendel L. Nelson、Peter J. Wirth

  DOI：10.1021/jm00357a027

  日期：1983.3

  Potential precursors to chemically reactive species derived from the beta-adrenergic antagonist propranolol were synthesized and tested for mutagenicity in the Ames Salmonella assay. N-Hydroxypropranolol (1), the corresponding aldonitrone, 3-(1-naphthoxy)-2-hydroxypropionaldehyde N-isopropylnitrone (2), and N-nitrosopropranolol (3) were prepared and tested. N-Hydroxypropranolol (1) was obtained by direct alkylation of 3-(1-naphthoxy)-1-bromo-2-propanol with N-isopropylhydroxylamine and isolated as its neutral oxalate or HBr salt. The aldonitrone (2) was obtained by mercuric oxide oxidation of the hydroxylamine. N-Nitrosopropranolol (3) was prepared by treating propranolol with nitrous acid. None of the compounds was mutagenic in the Ames assay with Salmonella typhimurium TA-98 and TA-100 strains, either in the absence or in the presence of the S-9 liver fraction from Arochlor 1254 treated rats. None of the compounds was significantly toxic to the bacteria, except for slight toxicity of the oxalate salt of 1.