2,5-二溴苯甲醚 | 95970-08-4

• 物质功能分类: 有机原料 - 醚类化合物及其衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2,5-二溴苯甲醚
• 中文别名: 2,2,3,3,4,5,5,6,6-九溴联苯醚
• 英文名称: 1,4-dibromo-2-methoxybenzene
• 英文别名: 2,4-dibromoanisole；2,5-dibromoanisole；1,4-dibromo-2-methoxy-benzene；1,4-dibromo-3-methoxybenzene
• CAS: 95970-08-4
• 化学式: C₇H₆Br₂O
• 分子量: 265.932
• InChiKey: YJGNTPRGNRICPY-UHFFFAOYSA-N

物化性质

• 沸点：
  257-261 °C
• 密度：
  1.823±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

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

反应信息

• 作为反应物：
  描述：

  2,5-二溴苯甲醚 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 4.0h， 生成 2-(4-(1H-indol-2-yl)-2-methoxyphenyl)-6-bromo-1H-indole
  参考文献：
  名称：

  Discovery and optimization of a new class of pyruvate kinase inhibitors as potential therapeutics for the treatment of methicillin-resistant Staphylococcus aureus infections

  摘要：

  A novel series of bis-indoles derived from naturally occurring marine alkaloid 4 were synthesized and evaluated as inhibitors of methicillin-resistant Staphylococcus aureus (MRSA) pyruvate kinase (PK). PK is not only critical for bacterial survival which would make it a target for development of novel antibiotics, but it is reported to be one of the most highly connected 'hub proteins' in MRSA, and thus should be very sensitive to mutations and making it difficult for the bacteria to develop resistance. From the co-crystal structure of cis-3-4-dihydrohamacanthin B (4) bound to S. aureus PK we were able to identify the pharmacophore needed for activity. Consequently, we prepared simple direct linked bis-indoles such as 10b that have similar anti-MRSA activity as compound 4. Structure-activity relationship (SAR) studies were carried out on 10b and led us to discover more potent compounds such as 10c, 10d, 10k and 10m with enzyme inhibiting activities in the low nanomolar range that effectively inhibited the bacteria growth in culture with minimum inhibitory concentrations (MIC) for MRSA as low as 0.5 mu g/ml. Some potent PK inhibitors, such as 10b, exhibited attenuated antibacterial activity and were found to be substrates for an efflux mechanism in S. aureus. Studies comparing a wild type S. aureus with a construct (S. aureus LAC Delta pyk::ErmR) that lacks PK activity confirmed that bactericidal activity of 10d was PK-dependant. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.020
• 作为产物：
  描述：

  4'-甲氧基乙酰苯胺 在 盐酸 、 乙醇 、 硫酸 、 溴 、 sodium nitrite 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 6.25h， 生成 2,5-二溴苯甲醚
  参考文献：
  名称：

  Shishkin, V. N.; Tanaseichuk, B. S.; Lapin, K. K., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 2357 - 2366

  摘要：

  DOI：

文献信息

• Active Molybdenum-Based Anode for Dehydrogenative Coupling Reactions
  作者：Sebastian B. Beil、Timo Müller、Sydney B. Sillart、Peter Franzmann、Alexander Bomm、Michael Holtkamp、Uwe Karst、Wolfgang Schade、Siegfried R. Waldvogel

  DOI：10.1002/anie.201712718

  日期：2018.2.23

  and powerful active anode system that can be operated in 1,1,1,3,3,3‐hexafluoro‐2‐propanol (HFIP) has been discovered. In HFIP the molybdenum anode forms a compact, conductive, and electroactive layer of higher‐valent molybdenum species. This system can replace powerful but stoichiometrically required MoV reagents for the dehydrogenative coupling of aryls. This electrolytic reaction is more sustainable

  发现了一种可以在1,1,1,3,3,3-六氟-2-丙醇（HFIP）中运行的功能强大的新型阳极活性系统。在HFIP中，钼阳极形成一个高价钼物种的致密，导电和电活性层。该系统可替代功能强大但化学计量上要求的Mo V试剂，用于芳基的脱氢偶联。这种电解反应是更可持续的，并允许转化广泛范围的活化芳烃。
• [EN] THIENOPYRIDINE CARBOXAMIDES AS UBIQUITIN-SPECIFIC PROTEASE INHIBITORS<br/>[FR] THIÉNOPYRIDINE CARBOXAMIDES UTILISÉS COMME INHIBITEURS DE PROTÉASE SPÉCIFIQUE DE L'UBIQUITINE
  申请人：FORMA THERAPEUTICS INC

  公开号：WO2017139778A1

  公开（公告）日：2017-08-17

  The disclosure relates to inhibitors of USP28 and/or USP25 useful in the treatment of cancers, inflammation, autoimmune diseases, and infectious diseases, having the Formula (I), where R1, R2, R3, R4, R5, R5', R6, R7, X, m, and n are described herein.

  该披露涉及抑制剂USP28和/或USP25，用于治疗癌症、炎症、自身免疫疾病和传染病，具有式(I)，其中R1、R2、R3、R4、R5、R5'、R6、R7、X、m和n如本文所述。
• N-Protected 1,2-Oxazetidines as a Source of Electrophilic Oxygen: Straightforward Access to Benzomorpholines and Related Heterocycles by Using a Reactive Tether
  作者：Tomas Javorskis、Simona Sriubaitė、Gintautas Bagdžiūnas、Edvinas Orentas

  DOI：10.1002/chem.201500731

  日期：2015.6.15

  A hitherto unknown reactivity of a strained four‐membered heterocycle, 1,2‐oxazetidine, is reported. When reacted with organometallic compounds, this reagent provides electrophilic oxygen with a nitrogen‐terminated two‐carbon‐atom tether. The synthetic versatility of the products obtained was demonstrated in various transformations, leading to efficient synthesis of six‐, seven‐, and eight‐membered

  据报道，迄今为止，应变四元杂环1,2-氧氮杂环丁烷的反应性迄今未知。与有机金属化合物反应时，该试剂可提供带有氮封端的双碳原子束缚剂的亲电子氧。通过各种转化证明了所获得产品的合成多功能性，从而有效合成了具有重要性的六元，七元和八元杂环系统。
• Transition-metal-free decarboxylative bromination of aromatic carboxylic acids
  作者：Jacob M. Quibell、Gregory J. P. Perry、Diego M. Cannas、Igor Larrosa

  DOI：10.1039/c8sc01016a

  日期：——

  Methods for the conversion of aliphatic acids to alkyl halides have progressed significantly over the past century, however, the analogous decarboxylative bromination of aromatic acids has remained a longstanding challenge. The development of efficient methods for the synthesis of aryl bromides is of great importance as they are versatile reagents in synthesis and are present in many functional molecules

  在过去的一个世纪中，将脂肪酸转化为卤代烷的方法取得了显着进展，然而，芳香族酸的类似脱羧溴化仍然是一个长期的挑战。开发有效的芳基溴化物合成方法非常重要，因为它们是合成中的通用试剂，并且存在于许多功能分子中。在此，我们报告了芳香族酸的无过渡金属脱羧溴化反应。该反应适用于许多富含电子的芳族和杂芳族酸，这些酸先前已被证明是Hunsdiecker型反应的不良底物。此外，我们的初步机理研究表明，自由基中间体不参与该反应，这与经典的Hunsdiecker型反应性相反。全面的，
• METHOD FOR MANUFACTURING CONJUGATED AROMATIC COMPOUND
  申请人：Oda Seiji

  公开号：US20110275859A1

  公开（公告）日：2011-11-10

  A method for manufacturing a conjugated aromatic compound comprising reacting an aromatic compound (A) wherein one or two leaving groups selected from the group consisting of an iodine atom, a bromine atom and a chlorine atom are bonded to an aromatic ring and the aromatic compound (A) does not have (c1) a group represented by the following formula (10): wherein A 1 represents a C1-C20 alkoxy group etc.; (g1) a C1-C20 alkyl group which may be substituted with a fluorine atom etc.; and (h1) a C2-C20 acyl group which may be substituted with a fluorine atom etc., at the neighboring carbon atom to the carbon atom to which the leaving group is bonded, with an aromatic compound (A) having the same structure as that of the above-mentioned aromatic compound (A) or an aromatic compound (B) wherein the aromatic compound (B) is structurally different from the above-mentioned aromatic compound (A), one or two leaving groups selected from the group consisting of an iodine atom, a bromine atom and a chlorine atom are bonded to an aromatic ring and the aromatic compound (B) does not have the above-mentioned (c1), (g1) and (h1) at the neighboring carbon atom to the carbon atom to which the leaving group is bonded, in the presence of (i) a nickel compound, (ii) a metal reducing agent, (iii) at least one ligand (L1) selected from the group consisting of a 2,2′-bipyridine compound having at least one electron-withdrawing group and having no substituent at 3-, 6-, 3′- and 6′-positions, and a 1,10-phenanthroline compound having at least one electron-withdrawing group and having no substituent at 2- and 9-positions, and (iv) at least one ligand (L2) selected from the group consisting of a 2,2′-bipyridine compound having at least one electron-releasing group and having no substituent at 3-, 6-, 3′- and 6′-positions, and a 1,10-phenanthroline compound having at least one electron-releasing group and having no substituent at 2- and 9-positions.

  一种制备共轭芳香化合物的方法，包括将含有一个或两个离去基团的芳香化合物（A）与含有相同结构的上述芳香化合物（A）或结构不同的芳香化合物（B）反应，其中这些离去基团选自碘原子、溴原子和氯原子，与芳香环结合，而芳香化合物（A）没有以下式（10）所代表的基团：其中A1代表C1-C20烷氧基等；（g1）代表C1-C20烷基基团，可能被氟原子等取代；以及（h1）代表C2-C20酰基基团，可能被氟原子等取代，与离去基团结合的碳原子的相邻碳原子处没有上述（c1）、（g1）和（h1），在（i）镍化合物、（ii）金属还原剂、（iii）从2,2′-联吡啶化合物和1,10-邻菲啰啉化合物中选择的至少一种配体（L1），具有至少一个吸电子基团且在3-、6-、3′-和6′-位置没有取代基，以及（iv）从2,2′-联吡啶化合物和1,10-邻菲啰啉化合物中选择的至少一种配体（L2），具有至少一个释电子基团且在3-、6-、3′-和6′-位置没有取代基团的情况下，在上述离去基团结合的碳原子的相邻碳原子处进行反应。