1-(N-isopropylacetamido)-3-(naphthalen-1-yloxy)propan-2-yl acetate | 70153-33-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(N-isopropylacetamido)-3-(naphthalen-1-yloxy)propan-2-yl acetate
• 英文别名: Acetamide, N-(2-(acetyloxy)-3-(1-naphthalenyloxy)propyl)-N-(1-methylethyl)-；[1-[acetyl(propan-2-yl)amino]-3-naphthalen-1-yloxypropan-2-yl] acetate
• CAS: 70153-33-2
• 化学式: C₂₀H₂₅NO₄
• 分子量: 343.423
• InChiKey: PIVFTODZBDQMRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(N-isopropylacetamido)-3-(naphthalen-1-yloxy)propan-2-yl acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以78%的产率得到N-[2-羟基-3-(1-萘氧基)丙基】-N-(1-甲基乙基)甲酰胺
  参考文献：
  名称：

  Photodegradation products of propranolol: The structures and pharmacological studies

  摘要：

  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.

  DOI：

  10.1016/j.lfs.2005.04.033
• 作为产物：
  描述：

  乙酸酐 、 普萘洛尔 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以54%的产率得到1-(N-isopropylacetamido)-3-(naphthalen-1-yloxy)propan-2-yl acetate
  参考文献：
  名称：

  Easy kinetic resolution of some β-amino alcohols by Candida antarctica lipase B catalyzed hydrolysis in organic media

  摘要：

  DOI：

  10.1016/j.tetasy.2016.10.003

文献信息

• Visible Light-Induced Borylation of C–O, C–N, and C–X Bonds
  作者：Shengfei Jin、Hang. T. Dang、Graham C. Haug、Ru He、Viet D. Nguyen、Vu T. Nguyen、Hadi D. Arman、Kirk S. Schanze、Oleg V. Larionov

  DOI：10.1021/jacs.9b12519

  日期：2020.1.22

  photocatalytic borylation method that can effect borylation of a wide range of substrates, including strong C‒O bonds, remains elusive. Herein, we report a general, metal-free visible light-induced photocatalytic borylation platform that enables borylation of electron rich derivatives of phenols and anilines, chloroarenes, as well as other haloarenes. The reac-tion exhibits excellent functional group

  硼酸是中心重要的功能基序和合成前体。可见光诱导的硼酸化可以提供结构多样化的硼酸盐，但一种广泛有效的光催化硼酸化方法可以影响包括强 C-O 键在内的多种底物的硼化，仍然难以实现。在此，我们报告了一种通用的、无金属的可见光诱导光催化硼化平台，该平台能够对苯酚和苯胺、氯芳烃以及其他卤代芳烃的富电子衍生物进行硼化。该反应表现出优异的官能团耐受性，正如一系列结构复杂底物的硼化反应所证明的那样。值得注意的是，该反应是由吩噻嗪催化的，这是一种简单的有机光催化剂，MW< 200通过质子耦合电子转移机制介导了以前无法实现的可见光诱导的苯酚衍生物单电子还原，还原电位为~-3 V vs SCE。机理研究指出了光催化剂-碱相互作用的关键作用。
• Facile Synthesis of Propranolol and Novel Derivatives
  作者：Vy Anh Tran、Nguyen Hai Tai Tran、Long Giang Bach、Trinh Duy Nguyen、Thi Thuong Nguyen、Tan Tai Nguyen、Thi Anh Nga Nguyen、The Ky Vo、Thu-Thao Thi Vo、Van Thuan Le

  DOI：10.1155/2020/9597426

  日期：2020.8.24

  Propranolol is one of the first medications of the beta-blocker used for antihypertensive drugs. This study reports the facile route for the synthesis of propranolol and its novel derivatives. Herein, propranolol synthesis proceeded from 1-naphthol and isopropylamine under mild and less toxic conditions. Novel propranolol derivatives were designed by reactions of propranolol with benzoyl chloride,

  心得安是用于抗高血压药物的β受体阻滞剂的首批药物之一。本研究报告了合成普萘洛尔及其新型衍生物的简便途径。在此，普萘洛尔在温和且毒性较小的条件下由 1-萘酚和异丙胺合成。通过将普萘洛尔与苯甲酰氯、氯铬酸吡啶鎓和正丁基溴分别通过酯化、氧化还原和烷基化反应设计了新型普萘洛尔衍生物。使用柱色谱和薄层色谱进行化合物的分离和纯度。质谱和 1H-NMR 光谱用于鉴定新的化合物结构。来自 2-氯苯甲酰氯（化合物 3）、2-氟苯甲酰氯（化合物 5）的心得安衍生物，尤其是乙酸酐（化合物 6）表现出高产率和显着增加的水溶性。六种半合成的心得安衍生物有望提高抗氧化和生物活性。
• Ligand and counteranion enabled regiodivergent C–H bond functionalization of naphthols with α-aryl-α-diazoesters
  作者：Zhunzhun Yu、Yongfeng Li、Peichao Zhang、Lu Liu、Junliang Zhang

  DOI：10.1039/c9sc01657k

  日期：——

  an unprecedented ligand and counteranion-controlled and site-selectivity switchable direct C–H bond functionalization of unprotected naphthols with α-aryl-α-diazoesters was developed. In this transformation, site selectivities are realized by turning on/off the coordination between metal complexes and hydroxy groups. The preliminary mechanism revealed that the interaction between the hydroxy group

  在这里，开发了一种空前的配体和对阴离子控制的和位点选择性可转换的未保护的萘酚与α-芳基-α-二重氮酯的直接C–H键直接官能化。在该转化中，通过打开/关闭金属络合物与羟基之间的配位来实现位点选择性。初步机理表明，羟基与金催化剂之间的相互作用在切换金卡宾的位点选择性中起着关键作用。该协议可能为C–H键功能化提供一种新颖的设计。
• 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.
• US5334534A
  申请人：——

  公开号：US5334534A

  公开（公告）日：1994-08-02