2-(benzyloxy)naphthalene-1-carboxylic acid | 93655-27-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(benzyloxy)naphthalene-1-carboxylic acid
• 英文别名: 2-(benzyloxy)-1-naphthoic acid；2-benzyloxy-1-naphthoic acid；2-benzyloxynaphthoic acid；2-Benzyloxy-1-carboxy-naphthalin；2-phenylmethoxynaphthalene-1-carboxylic acid
• CAS: 93655-27-7
• 化学式: C₁₈H₁₄O₃
• mdl: MFCD04578310
• 分子量: 278.307
• InChiKey: AOCAFDPSJAOBOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.055
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(benzyloxy)naphthalene-1-carboxylic acid 在 palladium on activated charcoal ammonium hydroxide 、 草酰氯 、 氢气 、 N,N-二甲基甲酰胺 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 55.0h， 生成 ethyl 2-hydroxy-1-naphthimidate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Naphthyldesferrithiocin Iron Chelators

  摘要：

  The synthesis and iron-clearing properties of the naphthyldesferrithiocins 2-(2'-hydroxynaphth-1'-yl)-Delta(2)-thiazoline-(4R)-carboxylic acid, 2-(2'-hydroxynaphth-1'-yl)-Delta(2)-thiazoline-(4S)-carboxylic acid, 2-(3'-hydroxynaphth-2'-yl)-Delta(2)-thiazoline-(4R)-carboxylic acid, and 2-(3'-hydroxynaphth-2'-yl)-Delta(2)-thiazoline-(4S)-carboxylic acid are described. While the bile duct-cannulated rat model clearly demonstrates that the 3'-hydroxynaphthyl-2'-yl compounds are orally active iron-clearing agents and the corresponding 2'-hydroxynaphthyl-1'-yl compounds are not, in the primate model none of the bent-fused desazadesferrithiocin analogues are active. Oral versus subcutaneous administration of these ligands strongly suggests that metabolism is a key issue in their iron-clearing properties and that these bent-fused desferrithiocins are not good candidates for orally active iron-clearing drugs.

  DOI：

  10.1021/jm9508752
• 作为产物：
  描述：

  2-苄氧基-1-萘醛 在 sodium chlorite 、 氨基磺酸 作用下， 以 水 、 丙酮 为溶剂， 反应 0.5h， 以85%的产率得到2-(benzyloxy)naphthalene-1-carboxylic acid
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Naphthyldesferrithiocin Iron Chelators

  摘要：

  The synthesis and iron-clearing properties of the naphthyldesferrithiocins 2-(2'-hydroxynaphth-1'-yl)-Delta(2)-thiazoline-(4R)-carboxylic acid, 2-(2'-hydroxynaphth-1'-yl)-Delta(2)-thiazoline-(4S)-carboxylic acid, 2-(3'-hydroxynaphth-2'-yl)-Delta(2)-thiazoline-(4R)-carboxylic acid, and 2-(3'-hydroxynaphth-2'-yl)-Delta(2)-thiazoline-(4S)-carboxylic acid are described. While the bile duct-cannulated rat model clearly demonstrates that the 3'-hydroxynaphthyl-2'-yl compounds are orally active iron-clearing agents and the corresponding 2'-hydroxynaphthyl-1'-yl compounds are not, in the primate model none of the bent-fused desazadesferrithiocin analogues are active. Oral versus subcutaneous administration of these ligands strongly suggests that metabolism is a key issue in their iron-clearing properties and that these bent-fused desferrithiocins are not good candidates for orally active iron-clearing drugs.

  DOI：

  10.1021/jm9508752

文献信息

• 一种基于芳烃羧酸脱羧反应合成单碘代芳烃 或二碘代芳烃的方法
  申请人：湘潭大学

  公开号：CN106748604B

  公开（公告）日：2020-06-05

  本发明公开了一种基于芳烃羧酸脱羧反应合成单碘代芳烃或二碘代芳烃的方法，该方法是在保护气氛下，芳烃羧酸和碘化试剂在钯催化剂作用下，一锅反应，得到单碘代芳烃或二碘代芳烃；该方法具有原料便宜易得、反应步骤少、条件温和、操作简单安全等特点。
• Thiazoline acid derivatives
  申请人：University of Florida Research Foundation, Inc.

  公开号：US05840739A1

  公开（公告）日：1998-11-24

  Thiazoline acids and derivatives useful as chelators of trivalent metals in therapeutic applications have been prepared.

  已经制备出可用作治疗应用中三价金属螯合剂的噻唑酸及其衍生物。
• [EN] THIAZOLINE ACID DERIVATIVES<br/>[FR] DERIVES D'ACIDE DE THIAZOLINE
  申请人：UNIVERSITY OF FLORIDA

  公开号：WO1997036885A1

  公开（公告）日：1997-10-09

  (EN) 2-(2-Hydroxy aryl)-thiazoline-4-carboxylic acids and derivatives are useful as chelators of trivalent metals in therapeutic applications.(FR) L'invention a pour objet des acides 2-(2-hydroxy aryl)-thiazoline-4-carboxyliques et leurs dérivés, qui sont utiles comme chélatants de métaux trivalents dans des applications thérapeutiques.

  2-(2-羟基苯基)噻唑线-4-酸和衍生物，在治疗应用中，它们作为三价金属的配位剂有用。
• An efficient chemoselective etherification of phenols in polyfunctional aromatic compounds
  作者：Jyoti Pandey、Mridul Mishra、Surendra Singh Bisht、Anindra Sharma、Rama P. Tripathi

  DOI：10.1016/j.tetlet.2007.11.129

  日期：2008.1

  A simple and efficient chemoselective alkylation of phenols in polyfunctional aromatic compounds with different alkyl halides in the presence of K2CO3/TBAB is reported. The method is successful with various hydroxy aromatic acids or oximes possessing other functional groups. (c) 2007 Elsevier Ltd. All rights reserved.
• COMPOSITIONS AND METHODS FOR THE TREATMENT OF IMMUNOMEDIATED INFLAMMATORY DISORDERS
  申请人：ARRIS PHARMACEUTICAL CORPORATION

  公开号：EP0688337A1

  公开（公告）日：1995-12-27