4-溴-1-羟基-2-萘乙酮 | 52220-64-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 4-溴-1-羟基-2-萘乙酮
• 英文名称: 2-acetyl-4-bromo-1-naphthol
• 英文别名: 1-(4-Bromo-1-hydroxynaphthalen-2-yl)ethanone
• CAS: 52220-64-1
• 化学式: C₁₂H₉BrO₂
• 分子量: 265.106
• InChiKey: NMDZQQHBPKCHBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  4-溴-1-羟基-2-萘乙酮 在 吡啶 、 potassium phosphate 、 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 1-(1,4-bis(2-chlorophenyl)naphthalen-2-yl)ethanone
  参考文献：
  名称：

  Synthesis of aryl-substituted naphthalenes by chemoselective Suzuki–Miyaura reactions of bromo-trifluoromethanesulfonyloxy-naphthalenes. Influence of steric and electronic parameters

  摘要：

  Chemoselective Suzuki-Miyaura reactions of 2-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, 1-bromo-2-(trifluoromethanesulfonyloxy) naphthalene and 2-acetyl-4-bromo-1-(trifluoromethanesulfonyloxy)naphthalene, which are all readily available from the corresponding tetralone derivatives, afforded a variety of mono- and diarylnaphthalenes. The reactions generally proceed with excellent chemoselectivity in favour of the bromide position, no matter whether the bromide is located at position 1 or 2 of the naphthalene or whether the carbon attached to the triflate group is electronically more deficient by the presence of a neighbouring acetyl group. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.026
• 作为产物：
  描述：

  3-乙酰基-4-羟基-萘-1-磺酸 在 溴 、 溶剂黄146 作用下， 生成 4-溴-1-羟基-2-萘乙酮
  参考文献：
  名称：

  Fries; Schimmelschmidt, Chemische Berichte, 1925, vol. 58, p. 2844

  摘要：

  DOI：

文献信息

• PdCl ₂ /CuCl ₂ /Bi(OTf) ₃ ‐promoted Construction of Sulfonyl Dibenzooxabicyclo[3.3.1]nonanes and Arylnaphthalenes via Intramolecular Annulation of Sulfonyl <i>o</i> ‐Allylarylchromanones
  作者：Nai‐Chen Hsueh、Meng‐Yang Chang

  DOI：10.1002/adsc.202001021

  日期：2020.12.22

  PdCl2/CuCl2/Bi(OTf)3‐promoted intramolecular domino annulation of sulfonyl o‐allylarylchromanones provides tetracyclic sulfonyl dibenzooxabicyclo[3.3.1]nonanes and bicyclic arylnaphthalenes with good to excellent yields in MeOH at room (25 °C) and refluxing (65 °C) temperature, respectively. The starting sulfonyl o‐allylarylchromanones can be easily obtained from the intermolecular cyclocondensation of α‐sulfonyl

  PdCl 2 / CuCl 2 / Bi（OTf）3促进的磺酰基邻烯丙基芳基苯并二氢呋喃酮分子内环化反应提供了四环磺酰基二苯并氧杂双环[3.3.1]壬烷和双环芳基萘，在室温（25°C）和回流条件下，在MeOH中的产率高至优异（65°C）温度。起始磺酰ø -allylarylchromanones可以从α磺酰基的分子间环化缩合而容易地获得ö -hydroxyacetophenones和ö烯丙基甲醛。为了方便的转化，本文研究了各种催化剂和溶剂体系的用途。提出并讨论了一种可行的机制。该协议通过碳-碳（CC）键的形成提供一锅闭环。
• Benzoflavone activators of the cystic fibrosis transmembrane conductance regulator: towards a pharmacophore model for the nucleotide-binding domain
  作者：Mark F Springsteel、Luis J.V Galietta、Tonghui Ma、Kolbot By、Gideon O Berger、Hong Yang、Christopher W Dicus、Wonken Choung、Chao Quan、Anang A Shelat、R.Kiplin Guy、A.S Verkman、Mark J Kurth、Michael H Nantz

  DOI：10.1016/s0968-0896(03)00435-8

  日期：2003.9

  using cell-based assays, of a series of benzoflavone analogues to examine structure-activity relationships and to identify compounds having greater potency for activation of both wild type CFTR and a mutant CFTR (G551D-CFTR) that causes cystic fibrosis in some human subjects. Using UCCF-029 as a structural guide, a panel of 77 flavonoid analogues was prepared. Analysis of the panel in FRT cells indicated

  我们以前对黄酮类化合物和相关杂环的筛选具有激活囊性纤维化跨膜电导调节剂（CFTR）氯化物通道的能力，这表明UCCF-029是一种7,8-苯并黄酮，是一种有效的活化剂。在本研究中，我们描述了使用基于细胞的分析方法对一系列苯并黄酮类似物进行合成和评估，以检查其结构活性关系，并鉴定出对野生型CFTR和突变型CFTR（G551D -CFTR）在某些人类受试者中引起囊性纤维化。使用UCCF-029作为结构指导，制备了77种类黄酮类似物。对FRT细胞中面板的分析表明，黄酮A环在7,8位的苯环显着提高了化合物活性和几种类黄酮的效力。在3或4位上引入B环吡啶基氮也可提高CFTR活性，但这种结构修饰的影响不如苯甲环化均匀。最有效的新类似物UCCF-339以1.7 microM的K（d）激活了野生型CFTR，它比以前最有效的CFTR类黄酮活化剂芹菜素具有更高的活性。苯并黄酮类化合物中的几种化合物也可以活化G5
• Preparation, spectral study and antimicrobial activity of binary Co(II) complexes derived from 2’-hydroxy chalcones
  作者：P. Patil、S. Zangade

  DOI：10.4314/bcse.v35i3.4

  日期：——

  ABSTRACT. The present work comprises preparation, characterization, thermal behavior and growth inhibitory activity of some novel Co(II) complexes derived from substituted (E)-1-(1-hydroxy-4-iodonaphthalen-2-yl)-3-phenylprop-2-en-1-one (L1) and (E)-1-(4-bromo-1-hydroxynaphthalen-2-yl)-3-phenylprop-2-en-1-one (L2-L6). Newly synthesized metal-ligand complexes were structurally confirmed with suitable spectroscopic technique such as FT-IR, EPR, NMR (both 1H and 13C). XRD analysis for complex C1 confirmed the crystal system; tetragonal and space group; P 42/n: 2 with unit cell dimensions a, b = 13.3516 Å, c = 10.8009 Å; α, β, γ = 90o. The IR and EPR study demonstrated that interaction between metal ions and ligand occurs through carbonyl oxygen and hydroxyl oxygen. From the values of magnetic moment (μ) it was observed that synthesized complexes (C1-C6) are paramagnetic with three unpaired electrons contain one electron in t2g orbital and two electrons in eg orbitals. Further all these complexes have been evaluated in-vitro for their antimicrobial activity against the Gram positive bacteria Staphylococcus aureus, Gram negative bacteria Escherichia coli and the yeast Candida albicans. The complex C1 showed the significant antimicrobial activity, whereas the complexes C2, C4, C5 and C6 are moderately active against the tested pathogens. The antimicrobial data revealed that growth inhibitory activities of complexes were enhanced comparatively than its respective ligands. The enhanced antimicrobial activity is attributed to the presence of halogens (Br, Cl, I) and hydroxyl (OH) active substituents associated with the basic nucleus of complexes. Therefore, the present study helps to develop a new class of antimicrobial analogues.                     KEY WORDS: Metal complexes synthesis, 1,3-Diaryl-2-propene-1-one, Crystal structure, Thermal properties, Antimicrobial activity   Bull. Chem. Soc. Ethiop. 2021, 35(3), 513-524. DOI: https://dx.doi.org/10.4314/bcse.v35i3.4

  摘要：本研究包括制备、表征、热行为和生长抑制活性的一些新型Co（II）配合物，这些配合物来自于取代的（E）-1-（1-羟基-4-碘萘-2-基）-3-苯基丙-2-烯-1-酮（L1）和（E）-1-（4-溴-1-羟基萘-2-基）-3-苯基丙-2-烯-1-酮（L2-L6）。新合成的金属配体配合物通过适当的光谱技术（如FT-IR、EPR、NMR（1H和13C））进行了结构确认。复合物C1的XRD分析证实了晶体系统；四方晶系和空间群；P 42/n：2，具有单元格尺寸a、b = 13.3516 Å，c = 10.8009 Å；α，β，γ = 90o。IR和EPR研究表明，金属离子和配体之间的相互作用是通过羰基氧和羟基氧发生的。从磁矩（μ）值可以观察到，合成的配合物（C1-C6）是顺磁性的，含有三个未成对电子，其中一个电子在t2g轨道中，两个电子在eg轨道中。进一步，所有这些配合物已经在体内评估其抗菌活性，对革兰氏阳性细菌金黄色葡萄球菌、革兰氏阴性细菌大肠杆菌和酵母菌白色念珠菌。复合物C1显示出显著的抗菌活性，而复合物C2、C4、C5和C6对测试的病原体具有中等活性。抗菌数据表明，与其相应的配体相比，复合物的生长抑制活性得到了增强。增强的抗菌活性归因于卤素（Br、Cl、I）和羟基（OH）活性取代基与配合物的基本核心相关。因此，本研究有助于开发一类新的抗菌类似物。 关键词：金属配合物合成，1,3-二芳基-2-丙烯-1-酮，晶体结构，热性质，抗菌活性 《埃塞俄比亚化学学会杂志》2021年，35（3），513-524。 DOI：https://dx.doi.org/10.4314/bcse.v35i3.4
• Dimethyl Sulfoxide Provides Three Different Units in Synthesis of Chroman-4-ones Containing Sulfur and a Quaternary Carbon Center under HOAc Conditions
  作者：Lihong Xu、Anan Wang、Xu Shi、Qian He、Tao-Shan Jiang

  DOI：10.1021/acs.joc.3c00832

  日期：2023.10.6

  enones and DMSO is described. In these unique reactions, DMSO is activated by HOAc and provides three different units (CH2, CH2OH, and CH2SMe) in the target molecules. This reaction displays good substrate scope and reaction yields with a series of substitutes. The mechanism showed that the three units were formed in sequential order.

  描述了直接从邻羟基苯乙酮和 DMSO直接由 HOAc 促进的具有硫原子和 α-羰基季碳中心的色满-4-酮的构建。在这些独特的反应中，DMSO 被 HOAc 激活并在目标分子中提供三种不同的单元（CH 2、CH 2 OH 和 CH 2 SMe）。该反应显示出良好的底物范围和一系列替代物的反应产率。该机制表明，这三个单元是按顺序形成的。
• Enantioselective Intramolecular <i>ortho</i> Photocycloaddition Reactions of 2‐Acetonaphthones
  作者：Peng Yan、Simone Stegbauer、Qinqin Wu、Elena Kolodzeiski、Christopher J. Stein、Ping Lu、Thorsten Bach

  DOI：10.1002/anie.202318126

  日期：2024.3.22

  The intramolecular ortho photocycloaddition of 2-acetonaphthones has been achieved with high enantioselectivity. The catalytic use of a chiral Lewis acid was critical for the success of the reaction and its mode of action has been elucidated by mechanistic experiments and calculations. The primary photocycloaddition products underwent photochemically or thermally a variety of consecutive reactions

  2-丙酮萘的分子内邻位光环加成反应具有高对映选择性。手性路易斯酸的催化使用对于反应的成功至关重要，其作用模式已通过机械实验和计算得到阐明。初级光环加成产物经历光化学或热的各种连续反应。