普萘洛尔杂质 | 77252-87-0

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 普萘洛尔杂质
• 中文别名: N-[2-羟基-3-(1-萘氧基)丙基]-N-(1-甲基乙基)甲酰胺；N-[2-羟基-3-(1-萘氧基)丙基】-N-(1-甲基乙基)甲酰胺
• 英文名称: 1-<<(1-methylethyl)-formyl>amino>-3-(1-naphthalenyloxy)-2-propanol
• 英文别名: N-[2-hydroxy-3-(1-naphthalenyloxy)propyl]-N-(1-methylethyl)formamide；(+/-)-N-formylpropranolol；N-formylpropranolol；N-(2-hydroxy-3-(naphthalen-1-yloxy)propyl)-n-isopropylformamide；N-(2-hydroxy-3-naphthalen-1-yloxypropyl)-N-propan-2-ylformamide
• CAS: 77252-87-0
• 化学式: C₁₇H₂₁NO₃
• 分子量: 287.359
• InChiKey: HYXSVEOUQCJDND-UHFFFAOYSA-N

物化性质

• 沸点：
  524.6±40.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  双乙烯酮 、 普萘洛尔杂质 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以55%的产率得到Iyllhqfuqmylay-uhfffaoysa-
  参考文献：
  名称：

  Acetoacetylation with Diketene Catalyzed by 4-Dimethylaminopyridine

  摘要：

  报道了一种有效的方法，将醇1与双酮烯酮2进行乙酰乙酰化反应，生成乙酰乙酸酯3。

  DOI：

  10.1055/s-1989-27260
• 作为产物：
  描述：

  potassium cyanide 、 普萘洛尔 在 水 、 丙二酸二甲酯 作用下， 以 甲醇 为溶剂， 反应 52.0h， 以62%的产率得到普萘洛尔杂质
  参考文献：
  名称：

  新型的N-甲酰化和胺通过氰化物和酯类作为甲酰化剂的相关反应。

  摘要：

  酯促进的氰化物引发了新的N-甲酰化反应和相关的反应。

  DOI：

  10.1039/b810086a

文献信息

• Approaches to Mutual Prodrugs: Calcium - β-Blockers
  作者：Abraham Nudelman、Rachel Kelner

  DOI：10.1002/ardp.19933261112

  日期：——
• 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.
• Acetoacetylation with Diketene Catalyzed by 4-Dimethylaminopyridine
  作者：Abraham Nudelman、Rachel Kelner、Neomi Broida、Hugo E. Gottlieb

  DOI：10.1055/s-1989-27260

  日期：——

  A useful procedure for the acetoacetylation of alcohols 1 with diketene 2 to acetoacetic esters 3 is reported.

  报道了一种有效的方法，将醇1与双酮烯酮2进行乙酰乙酰化反应，生成乙酰乙酸酯3。
• A novel type of N-formylation and related reactions of amines via cyanides and esters as formylating agents
  作者：Kai Bao、Weige Zhang、Xiujuan Bu、Zhichun Song、Liang Zhang、Maosheng Cheng

  DOI：10.1039/b810086a

  日期：——

  A novel N-formylation and related reactions proceed from cyanides promoted by esters.

  酯促进的氰化物引发了新的N-甲酰化反应和相关的反应。