2-(3-hydroxynaphthalen-2-yl)acetic acid | 305324-58-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(3-hydroxynaphthalen-2-yl)acetic acid
• 英文别名: 2-(3-Hydroxynaphthalen-2-yl)aceticacid
• CAS: 305324-58-7
• 化学式: C₁₂H₁₀O₃
• 分子量: 202.21
• InChiKey: PQFDONBGIMZFEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-hydroxynaphthalen-2-yl)acetic acid 在 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 15.0h， 以36 mg的产率得到naphtho[2,3-b]furan-2(3H)-one
  参考文献：
  名称：

  Pd(II)-Catalyzed ortho-C–H Oxidation of Arylacetic Acid Derivatives: Synthesis of Benzofuranones

  摘要：

  Pd(II)-catalyzed ortho-C-H acetoxylation of arylacetic acid derivatives is demonstrated with the aid of a novel S-methyl-S-2-pyridylsulfoximine (MPyS) directing group (DG). The alpha-mono- and alpha-unsubstituted arylacetic acid derivatives were readily employed in the ortho-C-H acetoxylations. The oxidation products are hydrolyzed, and the MPyS-DG is easily recovered, providing ready access to 0-hydroxyarylacetic acids. 3-Mono- and 3-unsubstituted benzofuranones are synthesized from 0-hydroxyarylacetic acids.

  DOI：

  10.1021/ol403699d
• 作为产物：
  描述：

  N-[2-(2-acetoxy-β-napthyl)acetyl]-S-methyl-S-2-pyridylsulfoximine 在 盐酸 、 水 作用下， 以83%的产率得到S-甲基-S-(2-吡啶基)亚磺酰亚胺
  参考文献：
  名称：

  Pd(II)-Catalyzed ortho-C–H Oxidation of Arylacetic Acid Derivatives: Synthesis of Benzofuranones

  摘要：

  Pd(II)-catalyzed ortho-C-H acetoxylation of arylacetic acid derivatives is demonstrated with the aid of a novel S-methyl-S-2-pyridylsulfoximine (MPyS) directing group (DG). The alpha-mono- and alpha-unsubstituted arylacetic acid derivatives were readily employed in the ortho-C-H acetoxylations. The oxidation products are hydrolyzed, and the MPyS-DG is easily recovered, providing ready access to 0-hydroxyarylacetic acids. 3-Mono- and 3-unsubstituted benzofuranones are synthesized from 0-hydroxyarylacetic acids.

  DOI：

  10.1021/ol403699d

文献信息

• Non-Amide-Based Combinatorial Libraries Derived fromN-Boc-Iminodiacetic Acid: Solution-Phase Synthesis of Piperazinone Libraries with Activity Against LEF-1/β-Catenin-Mediated Transcription
  作者：Dale L. Boger、Joel Goldberg、Shigeki Satoh、Yves Ambroise、Steven B. Cohen、Peter K. Vogt

  DOI：10.1002/1522-2675(20000809)83:8<1825::aid-hlca1825>3.0.co;2-4

  日期：2000.8.9

  methodology was applied to the synthesis of a diverse 150-member library with substituents in three positions of the piperazinone core. Screening results from a luciferase reporter assay indicate that a number of library members are novel repressors of LEF-1/β-catenin-mediated transcription, and may be effective agents against colorectal tumors. Two secondary libraries (100 members each) designed from

  详细介绍了从 N-Boc-亚氨基二乙酸开始仅需四个步骤即可快速、平行合成高度官能化哌嗪酮的溶液相方法。这些努力代表了组合文库的溶液相合成从 N-Boc-亚氨基二乙酸扩展到基于非酰胺的文库，其中使用简单的液-液萃取来纯化所有反应产物。该方法被应用于合成一个多样化的 150 成员库，在哌嗪酮核心的三个位置具有取代基。荧光素酶报告基因检测的筛选结果表明，许多文库成员是 LEF-1/β-连环蛋白介导的转录的新阻遏物，可能是对抗结肠直肠肿瘤的有效药物。合成和筛选了从这些先导结构设计的两个二级库（每个 100 个成员），提供额外的活性剂并深入了解该系列中的关键结构-活性关系。这些化合物仅代表第二类小分子，其抑制含有 LEF-1 响应元件的报告基因的转录，第一类不基于 DNA 小沟结合剂。
• Substituted bis-indole derivatives useful as contrast agents, pharmaceutical compositions containing them and intermediates for producing them
  申请人：——

  公开号：US20040053911A1

  公开（公告）日：2004-03-18

  Metal-complexable substituted bis-indole derivatives comprising the structure shown in formula (I) hereunder: enantiomers and pharmaceutically acceptable salts thereof and metal complexes thereof, wherein L, R 1 , R 2 , R 3 , C 1 , C 2 , m, n, p, q and r are as defined in claim 1 for use as constrats agents.

  具有以下式子（I）所示结构的金属络合取代双吲哚衍生物：其对映体、药学上可接受的盐及其金属络合物，其中L、R1、R2、R3、C1、C2、m、n、p、q和r如权利要求1所定义，用作造影剂。
• Ligand-Enabled C–H Hydroxylation with Aqueous H₂O₂ at Room Temperature
  作者：Zhen Li、Han Seul Park、Jennifer X. Qiao、Kap-Sun Yeung、Jin-Quan Yu

  DOI：10.1021/jacs.2c08332

  日期：2022.10.5

  carboxyl-pyridone (CarboxPyridone) ligand that enables room-temperature Pd-catalyzed C–H hydroxylation of a broad range of benzoic and phenylacetic acids with an industry-compatible oxidant, aqueous hydrogen peroxide (35% H2O2). The scalability of this methodology is demonstrated by a 1000 mmol scale reaction of ibuprofen (206 g) using only a 1 mol % Pd catalyst loading. The utility of this protocol is further

  随着过去十年中大量Pd(II)催化的天然底物C-H活化反应的发展，开发能够在安全实用的条件下使用绿色氧化剂的催化剂已成为一个日益重要的挑战。值得注意的是，Pd(II) 催化剂与可持续含水 H 2 O 2的相容性一直是包括瓦克型氧化在内的催化领域的长期挑战。我们在此报道了一种双功能双齿羧基吡啶酮 (CarboxPyridone) 配体，该配体能够使用工业兼容的氧化剂过氧化氢水溶液 (35% H 2 O)在室温下 Pd 催化的各种苯甲酸和苯乙酸的 C-H 羟基化反应。2）。仅使用 1 mol% Pd 催化剂负载的布洛芬 (206 g) 的 1000 mmol 规模反应证明了该方法的可扩展性。通过产品的衍生化以及从使用该方法制备的苯酚中间体合成多氟天然产物古美斯坦和紫檀烯，进一步说明了该协议的实用性。
• LIGAND-ENABLED SCALABLE C-H HYDROXYLATION OF BENZOIC AND PHENYLACETIC ACIDS AT ROOM TEMPERATURE
  申请人：[en]THE SCRIPPS RESEARCH INSTITUTE

  公开号：WO2024054881A1

  公开（公告）日：2024-03-14

  The application discloses industry scalable methods of using bifunctional bidentate pyridone-carboxylic acid ligands, such as 2-methyl-2-(6-oxo-1,6-dihydropyridin-2-yl)propanoic acid, that enable room-temperature Pd-catalyzed C-H hydroxylation of a broad range of benzoic and phenylacetic acids with an industry-compatible oxidant, aqueous hydrogen peroxide, at room temperature. Further disclosed are methods of derivatization of the resulting hydroxylation products, synthesis of polyfluorinated natural products coumestan or pterocarpene from phenol building blocks, and hydroxylation of ibuprofen using this methodology,

  该申请公开了使用双功能双齿吡啶酮-羧酸配体（如 2-甲基-2-(6-氧代-1,6-二氢吡啶-2-基)丙酸）的工业可扩展方法，这些配体能够在室温下用工业兼容氧化剂过氧化氢水溶液催化多种苯甲酸和苯乙酸的 C-H 羟基化反应。进一步公开了衍生羟化产物的方法、从苯酚结构单元合成多氟天然产物香豆素或紫檀烯的方法，以及使用该方法羟化布洛芬的方法、
• Non-porphyrin compound for use as a diagnosticum and/or pharmaceutical
  申请人：K.U. LEUVEN RESEARCH & DEVELOPMENT

  公开号：EP0998946A1

  公开（公告）日：2000-05-10

  The invention relates to a non porphyrin compound or a pharmaceutically acceptable salt thereof, suitable for in vitro, in vivo and/or ex vivo use as a diagnosticum and/or pharmaceutical, said compound comprising: a targeting agent for targeting a specific area, such as an organ and/or tissue, a labelling agent L for labelling the targeted area; said targeting agent being connected to the labelling agent L, wherein said targeting agent comprises one or more substituted and/or unsubstituted organic ring compounds.

  本发明涉及一种非卟啉化合物或其药学上可接受的盐，适用于体外、体内和/或体外诊断和/或制药，所述化合物包括 靶向剂，用于靶向特定区域，如器官和/或组织、 用于标记目标区域的标记剂 L；所述靶向剂与标记剂 L 连接、 其中，所述靶向剂包括一种或多种取代和/或未取代的有机环化合物。