3-羟基-1-萘甲醛 | 91136-43-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 3-羟基-1-萘甲醛
• 英文名称: 3-hydroxy-1-naphthaldehyde
• 英文别名: 3-hydroxynaphthalene-1-carbaldehyde
• CAS: 91136-43-5
• 化学式: C₁₁H₈O₂
• 分子量: 172.183
• InChiKey: PLCQXZXTFCITAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  室温且干燥

反应信息

• 作为反应物：
  描述：

  3-羟基-1-萘甲醛 在 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 methyl 4-formyl-2-naphthoate
  参考文献：
  名称：

  Substituents at the naphthalene C3 position of (−)-Cercosporamide derivatives significantly affect the maximal efficacy as PPARγ partial agonists

  摘要：

  Peroxisome proliferator-activated receptor gamma (PPAR gamma) is a potential drug target for treating type 2 diabetes. The selective PPAR gamma modulators (SPPARMs), which partially activate the PPAR gamma transcriptional activity, are considered to improve the plasma glucose level with attenuated PPAR gamma related adverse effects. However, the relationships between desired pharmacological profiles and ligand specific PPAR gamma transcriptional profiles have been unclear. And there is also little knowledge of how to control ligand specific PPAR gamma transcriptional profiles. Herein, we present synthesis of novel derivatives containing substituent at naphthalene C3 position of compound 1. The novel derivatives showed various maximal efficacies as PPAR gamma partial agonist. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.066
• 作为产物：
  描述：

  哌啶-1-甲醛 、 1-溴-3-羟基萘 生成 3-羟基-1-萘甲醛
  参考文献：
  名称：

  Synthesis and reactivity of formyl-substituted photochromic 3,3-diphenyl-[3H]-naphtho[2,1-b]pyrans

  摘要：

  Synthetic accesses to formylated photochromic 3,3-diphenyl-[3H]-naphthopyrans (or 2H-benzochromenes) are developed through classical cyclization between appropriate hydroxynaphthaldehydes and 1,1-diphenylpropyne-1-ol and also via substituent transformations on the naphthopyran skeleton including bromine/lithium exchange and the oxidation of an hydroxymethyl group. Examples of formyl group reactivity (Wittig and Knoevenagel reactions, imine formation) from these compounds are given, showing their interest in the subsequent preparation of supramolecular systems involving a photoreactive entity. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00245-8

文献信息

• Copper-doped mesoporous silica supported dual acidic ionic liquid as an efficient and cooperative reusability catalyst for Biginelli reaction
  作者：Nan Yao、Ming Lu、Xiao Bing Liu、Jin Tan、Yu Lin Hu

  DOI：10.1016/j.molliq.2018.04.121

  日期：2018.7

  A series of MCM-41 supported functionalized ionic liquids doped with copper species were prepared, characterized and evaluated as catalysts in the Biginelli reaction. Most of these supported ionic liquids perform well in the reaction, especially the multifunctional copper coordinated MCM-41 supported heterogeneous catalysts (0.5)IL-TiCl5@[email protected](15) and (0.5)IL-HSO4@[email protected](15)

  制备了一系列掺杂有铜物质的MCM-41负载型官能化离子液体，对其进行了表征和评估，作为Biginelli反应的催化剂。这些负载型离子液体大多数在反应中表现良好，尤其是多官能铜配位的MCM-41负载型多相催化剂（0.5）IL-TiCl 5 @ [受电子邮件保护]（15）和（0.5）IL-HSO 4 @ [受电子邮件保护] ]（15）。催化试验表明，（0.5）IL-HSO 4@ [受电子邮件保护]（15）是Biginelli反应中最好的和强大的催化剂，用于制备3,4-二氢嘧啶酮，产率高至优异。通过过滤可以很容易地将催化剂从反应混合物中分离出来，并在六个连续的循环中重复使用，而不会明显降低催化活性。
• [EN] MATRIPTASE 2 INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE MATRIPTASE 2 ET LEURS UTILISATIONS
  申请人：DISC MEDICINE INC

  公开号：WO2020072580A1

  公开（公告）日：2020-04-09

  The present invention provides compounds for inhibiting matriptase 2, or a mutant thereof, and compositions and methods of use thereof.

  本发明提供了用于抑制matriptase 2或其突变体的化合物，以及它们的组合物和使用方法。
• [EN] 1-(3-(6-(3-HYDROXYNAPHTHALEN-1-YL)BENZOFURAN-2-YL)AZETIDIN-1YL)PROP-2-EN-1-ONE DERIVATIVES AND SIMILAR COMPOUNDS AS KRAS G12C MODULATORS FOR TREATING CANCER<br/>[FR] DÉRIVÉS DE 1-(3-(6-(3-HYDROXYNAPHTALEN-1-YL)BENZOFURAN-2-YL)AZÉTIDIN-1YL)PROP-2-EN-1-ONE ET COMPOSÉS SIMILAIRES UTILISÉS EN TANT QUE MODULATEURS DE KRAS G12C POUR LE TRAITEMENT DU CANCER
  申请人：ARAXES PHARMA LLC

  公开号：WO2018140513A1

  公开（公告）日：2018-08-02

  Compounds having activity as inhibitors of G12C mutant KRAS protein are provided. The compounds have the following structure (I): or a pharmaceutically acceptable salt, isotopic form or stereoisomer thereof, wherein A is a five-membered heteroaryl comprising 1 or 2 non-adjacent heteroatoms, inclusive of X and Y; W, X, Y, Z, L, L1, E, R1, R2b R2c and the dotted circle are as defined herein. Methods associated with preparation and use of such compounds, pharmaceutical compositions comprising such compounds and compounds for use in methods to modulate the activity of G12C mutant KRAS protein for treatment of disorders, such as cancer, are also provided. Preferred compounds are e.g. l-(3-(6-(3-hydroxynaphthalen-l- yl)benzofuran-2-yl)azetidin-lyl)prop-2-en-l-one derivatives and related compounds such as e.g. the corresponding derivatives with e.g. a benzoimidazole, indole, benzooxazole, imidazopyridine or imidazole core structure, substituted on ring A by e.g. azetidine, pyrrolidine, azepane or bicyclopentane-amine (L1) each substituted by e.g. propenone (E), and the core structure substituted on the six-membered ring with e.g. 3-hydroxynaphthalene or indazole or hydroxy-, alkoxy- and/or fluoro-substituted phenyl (R1).

  提供了作为G12C突变KRAS蛋白抑制剂活性的化合物。这些化合物具有以下结构（I）：或其药学上可接受的盐、同位素形式或立体异构体，其中A是一个包含1个或2个非相邻杂原子（包括X和Y）的五元杂芳基；W、X、Y、Z、L、L1、E、R1、R2b、R2c和虚线圆圈的定义如本文所述。还提供了与制备和使用这些化合物相关的方法，包括含有这些化合物的药物组合物和用于调节G12C突变KRAS蛋白活性以治疗癌症等疾病的方法中使用的化合物。优选的化合物例如是l-(3-(6-(3-羟基萘-1-基)苯并呋喃-2-基)氮杂环丙烷-1-基)丙-2-烯-1-酮衍生物和相关化合物，例如相应的具有苯并咪唑、吲哚、苯并噁唑、咪唑吡啶或咪唑核心结构的衍生物，环A上被例如氮杂环丙烷、吡咯烷、氮杂庚烷或双环戊烷胺（L1）取代，每个取代基例如是丙酮（E），并且核心结构在六元环上被例如3-羟基萘或吲唑或羟基、烷氧基和/或氟取代苯基（R1）取代。
• [EN] IMIDAZOTRIAZINE AND PYRROLOPYRIMIDINE DERIVATIVES AS KRAS G12C INHIBITORS<br/>[FR] DÉRIVÉS D'IMIDAZOTRIAZINE ET DE PYRROLOPYRIMIDINE UTILISÉS COMME INHIBITEURS DE KRAS G12C
  申请人：BEIGENE LTD

  公开号：WO2022028492A1

  公开（公告）日：2022-02-10

  Disclosed herein are imidazotriazine and pyrrolopyrimidine derivatives or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof useful as a G12C inhibitors, and a pharmaceutical composition comprising the same. Also disclosed herein is the use in manufacture of medicaments for treating cancer using the imidazotriazine and pyrrolopyrimidine derivatives or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof as G12C inhibitors.

  本文披露了咪唑三嗪和吡咯吡嘧啶衍生物或其立体异构体，或其药学上可接受的盐，其作为G12C抑制剂的有用性，以及包含它们的药物组合物。本文还披露了使用咪唑三嗪和吡咯吡嘧啶衍生物或其立体异构体，或其药学上可接受的盐作为G12C抑制剂制造药物治疗癌症的用途。
• An ultrafast BODIPY single molecular sensor for multi-analytes (acid/base/Cu2+/Bi3+) with different sensing mechanism
  作者：Yuting Chen、Houhe Pan、Fang Wang、Yunying Zhao、Haoyan Yin、Yuxiang Chen、Junlong Zhang、Jianzhuang Jiang

  DOI：10.1016/j.dyepig.2019.02.034

  日期：2019.6

  designed and synthesize. Single crystal X-ray diffraction analysis reveals the keto-enamine rather than the enol-imine constitution of the ortho-hydroxy naphthalene azomethine moiety in NAP-BODIPY. As a consequence, along with the conversion between acid and basic conditions in the mixed DMSO/H2O, the enol-keto tautomerization occurs in the ortho-hydroxy naphthalene azomethine moiety of NAP-BODIPY, resulting

  为了将来的实际应用，有必要开发仅具有单个荧光团和单个受体的荧光传感器以用于多种分析物的检测。在本工作中，已设计并合成了一种新型的分子传感器，该传感器包含单个受体（萘酚-甲亚胺基苯酚骨架）和单个荧光团（BODIPY）NAP-BODIPY。单晶X射线衍射分析揭示了NAP-BODIPY中的酮-烯胺而不是邻羟基萘偶氮甲亚胺部分的烯醇-亚胺结构。结果，随着酸和碱性条件在混合DMSO / H 2中的转化O，烯醇-酮互变异构发生在NAP-BODIPY的邻羟基萘偶氮甲亚胺部分，导致电子吸收光谱和荧光发射光谱发生多种变化。此外，在NAP-BODIPY溶液中添加Cu 2+会导致最大吸收率出现明显的红移，并且观察到的肉眼由于金属诱导的聚集相互作用而从浅橙色变为品红色混浊。然而，由于抑制了光诱导的电子转移过程，将Bi 3+添加到NAP-BODIPY溶液中比弱的荧光发射有明显的增强。随后将Cu 2+添加到NAP-BODIPY-Bi