N-[2-(2-methoxyphenoxy)ethyl]acetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-[2-(2-methoxyphenoxy)ethyl]acetamide
• 化学式: C₁₁H₁₅NO₃
• mdl: MFCD02063369
• 分子量: 209.245
• InChiKey: LYUSMRCJQLYGGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[2-(2-methoxyphenoxy)ethyl]acetamide 在 盐酸 作用下， 以 异丙醇 为溶剂， 反应 25.0h， 生成 (S)-(-)-卡维地洛
  参考文献：
  名称：

  Hybridization of β-Adrenergic Agonists and Antagonists Confers G Protein Bias

  摘要：

  Starting from the beta-adrenoceptor agonist isoprenaline and beta-blocker carvedilol, we designed and synthesized three different chemotypes of agonist/antagonist hybrids. Investigations of ligand-mediated receptor activation using bioluminescence resonance energy transfer biosensors revealed a predominant effect of the aromatic head group on the intrinsic activity of our ligands, as ligands with a carvedilol head group were devoid of agonistic activity. Ligands composed of a catechol head group and an antagonist-like oxypropylene spacer possess significant intrinsic activity for the activation of Gas, while they only show weak or even no beta-arrestin-2 recruitment at both beta(1)- and beta(2)-AR Molecular dynamics simulations suggest that the difference in G protein efficacy and beta-arrestin recruitment of the hybrid (S)-22, the full agonist epinephrine, and the beta(2)-selective, G protein-biased partial agonist salmeterol depends on specific hydrogen bonding between Ser(5.46) and Asn(6.55), and the aromatic head group of the ligands.

  DOI：

  10.1021/acs.jmedchem.9b00349
• 作为产物：
  描述：

  2-甲基-2-恶唑啉 、 木榴油 反应 20.0h， 以76%的产率得到N-[2-(2-methoxyphenoxy)ethyl]acetamide
  参考文献：
  名称：

  [EN] METHOD FOR PREPARING 2-ALKOXYPHENOXYETHANAMINES FROM 2-ALKOXYPHENOXYETHYLACETAMIDES
  [FR] PROCEDE DE PREPARATION DE 2-ALKOXYPHENOXYETHANAMINES A PARTIR DE 2-ALKOXYPHENOXYETHYLACETAMIDES

  摘要：

  本发明涉及一种制备2-烷氧基苯氧乙胺的方法，更具体地涉及制备新化学实体2-烷氧基苯氧乙基乙酰胺，特别是作为该方法中的中间体。对于那些熟练的工艺人员来说，一种便宜且易于执行的合成2-烷氧基苯氧乙胺的工业化过程一直是迫切需要的。因此，本发明的目的是提供一种便宜且易于执行的工业生产苯氧乙胺的方法。这一目的通过新的化学实体2-烷氧基苯氧乙酰胺的制备来实现，该化合物是通过将邻位取代酚与2-烷氧噁唑啉反应制备的。通过在有机或矿物酸（如盐酸和/或硫酸）存在下用水水解乙酰胺，可以得到2-烷氧基苯氧乙胺。

  公开号：

  WO2003095416A1

文献信息

• Design, synthesis, and pharmacological effects of structurally simple ligands for MT1 and MT2 melatonin receptors
  作者：Alessia Carocci、Alessia Catalano、Angelo Lovece、Giovanni Lentini、Andrea Duranti、Valeria Lucini、Marilou Pannacci、Francesco Scaglione、Carlo Franchini

  DOI：10.1016/j.bmc.2010.06.100

  日期：2010.9

  A series of phenoxyalkyl and phenylthioalkyl amides were prepared as melatoninergic ligands. Modulation of affinity of the newly synthesized compound by applying SARs around the terminal amide moiety, the alkyl chain, and the methoxy group on the aromatic ring provides compounds with nanomolar affinity for both melatonin receptor subtypes. Affinity towards MT1 and MT2 receptors were modulated also exploiting chirality. The investigation of intrinsic activity revealed that all the tested compounds behave as full or partial agonists. (C) 2010 Elsevier Ltd. All rights reserved.
• METHOD FOR PREPARING 2-ALKOXYPHENOXYETHANAMINES FROM 2-ALKOXYPHENOXYETHYLACETAMIDES
  申请人：MCM PHARMA GMBH

  公开号：EP1506156A1

  公开（公告）日：2005-02-16
• PROCESS FOR THE PREPARATION OF CARVEDILOL AND ITS ENANTIOMERS
  申请人：Trepat Guixer Elisenda

  公开号：US20090005429A1

  公开（公告）日：2009-01-01

  The present invention relates to a process for the preparation of carvedilol as well as of the optically active R and S enantiomers thereof and of mixtures of these enantiomers and, more particularly, relates to an improved process for the preparation of carvedilol and its enantiomers characterized by the use of ethyl acetate as reaction solvent.