N-[2-formyloxy-3-(1-naphthalenyloxy)propyl]-N-(1-methylethyl)formamide | 149874-33-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[2-formyloxy-3-(1-naphthalenyloxy)propyl]-N-(1-methylethyl)formamide
• 英文别名: N,O-diformyl propranolol；N,O-diformylpropranolol；N-[2-(Formyloxy)-3-(1-naphthalenyloxy)propyl]-N-(1-methylethyl)formamide；[1-[formyl(propan-2-yl)amino]-3-naphthalen-1-yloxypropan-2-yl] formate
• CAS: 149874-33-9
• 化学式: C₁₈H₂₁NO₄
• 分子量: 315.369
• InChiKey: FYMUEMPBEJMIRW-UHFFFAOYSA-N

物化性质

• 沸点：
  529.6±45.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲酸 、 普萘洛尔 反应 12.0h， 以16%的产率得到N-[2-formyloxy-3-(1-naphthalenyloxy)propyl]-N-(1-methylethyl)formamide
  参考文献：
  名称：

  Biocatalytic resolution of DL-propranolol. A successful example of computer-aided substrate design

  摘要：

  An approach entailing computer-aided substrate design was taken to develop biocatalytic resolution of racemic propranolol. This strategy provided useful insight into potential steric factors within the substrate, which might be crucial to the catalytic turnover and enantiomeric selection.

  DOI：

  10.1016/s0040-4020(01)90157-7

文献信息

• Photodegradation products of propranolol: The structures and pharmacological studies
  作者：Koji Uwai、Marie Tani、Yosuke Ohtake、Shinya Abe、Akiko Maruko、Takashi Chiba、Yoshiro Hamaya、Yasuhito Ohkubo、Mitsuhiro Takeshita

  DOI：10.1016/j.lfs.2005.04.033

  日期：2005.12

  Recently, single-dose drug packaging systems, allowing the administration of multiple drugs in a single pill, have become popular for the convenience of the patient. The quality of drugs and an accurate measurement of their photostabilities within this system, however, have not been carefully addressed. Drugs that are unstable in light should be carefully handled to protect their potency and ensure their safety. Propranolol (1), a beta-adrenergic receptor antagonist, is widely used for angina pectoris, arrhythmia, and hypertension. Due to its naphthalene skeleton, this drug may be both light unstable and a photosensitizing agent. In this study, we isolated three photodegraded products of propranolol (1): 1-naphthol (2), N-acetylpropranolol (3), and N-formylpropranolol (4). The structures of these compounds were determined by spectroscopic methods and chemical syntheses. We also examined the acute toxicities of these substances in mice and their binding to beta-adrenergic receptors using rat cerebellum cortex membranes. Although the photoproducts isolated in this study did not exhibit any acute toxicity or significant binding to p-adrenergic receptors, these results serve as a warning to single-dose packaging systems, as propranolol (1) must be handled carefully to protect the compound from light-induced degradation. (c) 2005 Elsevier Inc. All rights reserved.
• US5334534A
  申请人：——

  公开号：US5334534A

  公开（公告）日：1994-08-02
• Biocatalytic resolution of DL-propranolol. A successful example of computer-aided substrate design
  作者：Ching-Shih Chen、Da-Ming Gou、Woan-Ru Shieh、Yeuk-Chuen Liu

  DOI：10.1016/s0040-4020(01)90157-7

  日期：1993.4

  An approach entailing computer-aided substrate design was taken to develop biocatalytic resolution of racemic propranolol. This strategy provided useful insight into potential steric factors within the substrate, which might be crucial to the catalytic turnover and enantiomeric selection.