(4-bromophenyl)(furan-2-yl)methanone | 13365-64-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-bromophenyl)(furan-2-yl)methanone
• 英文别名: 4-bromophenyl 2-furyl ketone；(4-bromo-phenyl)-[2]furyl ketone；(4-Brom-phenyl)-[2]furyl-keton；2-[(4-Bromophenyl)carbonyl]furan；(4-bromophenyl)-(furan-2-yl)methanone
• CAS: 13365-64-5
• 化学式: C₁₁H₇BrO₂
• mdl: MFCD09743319
• 分子量: 251.079
• InChiKey: ROQSRSVTBGSDJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-bromophenyl)(furan-2-yl)methanone 在 三氟甲磺酸 、 sodium hydride 作用下， 以 四氢呋喃 、 乙腈 、 mineral oil 为溶剂， 反应 24.0h， 生成 methyl 4-(3a-(4-bromophenyl)-2,4-dioxo-3,3a,4,6a-tetrahydrocyclopenta[b]pyrrol-1(2H)-yl)benzoate
  参考文献：
  名称：

  Retro-Aza-Piancatelli 重排引发呋喃基丙烯酸甲酯与苯胺的级联反应获得环戊二烯[b]吡咯烷酮

  摘要：

  利用呋喃基丙烯酸甲酯作为一种新型的功能化呋喃氧离子前体，开发了一种新型的 aza-Piancatelli 重排引发的级联反应，可以快速灵活地构建多种环戊二烯[ b ]吡咯烷酮衍生物。前所未有且高效的双环 γ-内酰胺产物的形成源于主要的顺式稠合多官能化环戊烯酮发生不寻常的逆-aza-Piancatelli 重排到次要的反式稠合的环戊烯酮，然后发生内酰胺化反应。

  DOI：

  10.1021/acs.joc.1c02546
• 作为产物：
  描述：

  (4-Bromo-phenyl)-furan-2-yl-methanone oxime 在 过碘酸 作用下， 反应 0.27h， 以91%的产率得到(4-bromophenyl)(furan-2-yl)methanone
  参考文献：
  名称：

  Solvent‐Free Rapid Deprotection of Ketone and Aldehyde Oximes using Periodic Acid

  摘要：

  Ketone and aldehyde oximes can be readily converted to the corresponding carbonyl compounds in high yields under solvent-free conditions when treated with periodic acid. Oximes bearing aliphatic C=C bonds can be selectively deoximated. The advantages of this protocol include a rapid reaction rate and a simple workup procedure. No volatile organic solvents are required in the reaction processes.

  DOI：

  10.1080/00397910500212833

文献信息

• Palladium-Catalyzed Denitrogenative Synthesis of Aryl Ketones from Arylhydrazines and Nitriles Using O₂ as Sole Oxidant
  作者：Xu Wang、Yubing Huang、Yanli Xu、Xiaodong Tang、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/acs.joc.6b02697

  日期：2017.2.17

  An efficient and simple palladium-catalyzed approach for the synthesis of aryl ketones from low-cost nitriles and arylhydrazines using molecular oxygen (O2) as sole oxidant via C–N bond cleavage is reported. Various aryl ketones were synthesized in moderate to good yields under mild conditions. A possible mechanism involving the PdII/Pd0 catalytic cycle process is depicted, and a cationic palladium

  据报道，一种有效且简单的钯催化方法可通过低成本的腈和芳肼，使用分子氧（O 2）作为唯一氧化剂通过C–N键断裂来合成芳基酮。在温和的条件下以中等至良好的产率合成了各种芳基酮。描述了涉及Pd II / Pd 0催化循环过程的可能机理，并通过ESI-MS检测了阳离子钯中间体。
• Infrared and nuclear magnetic resonance properties of benzoyl derivatives of five-membered monoheterocycles and determination of aromaticity indices
  作者：Kyu Ok Jeon、Jung Ho Jun、Ji Sook Yu、Chang Kiu Lee

  DOI：10.1002/jhet.5570400504

  日期：2003.9

  Benzophenones, 2-benzoylthiophenes, 2-benzoylpyrroles, and 2-benzoylfurans, which have substituents at m- and p-positions of the benzoyl ring were prepared and their ir and nmr spectra were obtained in 0.1 M chloroform-d solution. The chemical shift values of each series were plotted against the Hammett substituent parameters to give good correlation, with the exception of the ortho-Hs and -Cs. The

  二苯甲酮，2- benzoylthiophenes，2- benzoylpyrroles和2- benzoylfurans，其在具有取代基的米-和p苯甲酰基环的位上制备并在0.1，得到它们的红外和核磁共振光谱中号氯仿d溶液。将每个系列的化学位移值与哈米特取代基参数作图，以得到良好的相关性，但邻位-Hs和-Cs除外。斜率以及化学位移的差异为芳香性指数提供了一组有意义的值。
• Palladium-Catalyzed Chemoselective Cross-Coupling of Acyl Chlorides and Organostannanes
  作者：Rachel Lerebours、Alejandra Camacho-Soto、Christian Wolf

  DOI：10.1021/jo051257o

  日期：2005.10.1

  and alkynylstannanes proceeds in up to 98% yield using 2.5 mol % of bis(di-tert-butylchlorophosphine)palladium(II) dichloride as the precatalyst. Various functional groups including aryl chlorides and bromides that usually undergo oxidative addition to palladium complexes bearing phosphinous acid or dialkylchlorophosphine ligands are tolerated. This procedure allows convenient ketone formation and

  脂族和芳族酰氯与芳基-，杂芳基-和炔基锡烷的化学选择性交叉偶联使用2.5 mol％的二氯化二（二叔丁基氯膦）钯（II）作为预催化剂，产率高达98％。容许各种官能团，包括通常被氧化成带有亚膦酸或二烷基氯膦配体的钯络合物的氧化加成的芳基氯化物和溴化物。此程序可方便地形成酮，并消除了Friedel-Crafts酰化反应的内在限制，例如取代基导向作用和Lewis酸催化的亲电芳族取代的典型反应活性要求。
• Anti-coagulants of the 4-hydroxycoumarin type, the preparation thereof, and rodenticidal compositions (baits) comprising such anti-coagulants
  申请人：SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.

  公开号：EP0098629A1

  公开（公告）日：1984-01-18

  Compounds having blood-anticoagulant properties of the general molecular formula: in which Z represents a halogen atom, preferably a chlorine atom, and n ist 0, 1 or 2 and R4 represents either (1) a grouping which comprises a phenylene radical attached directly or indirectly to the tetralin ring and having in the para position (with respect to such attachment) an electron-withdrawing atom or group whose rotational volume substantially does not exceed that of a phenyl group and which forms together with said phenylene radical a polarisable structure, or (2) a grouping selected from: or (3) a grouping which comprises a phenylene radical attached directly to the tetralin ring and having In the para position (with respect to such attachment) a substituted furanyl or thiophenyl radical attached thereto directly or through oxygen and/or methylene, said furanyl or thiophenyl radical having such an electron-withdrawing atom or group as a substituent in a position forming with the furanyl or thiophenyl radical a polarisable structure. Compounds of the type (1) in which R4 contains two phenylene radicals linked essentially linearly by an aliphatic chain comprising a methylene radical or radicals and optionally at least one oxygen or sulphur atom being preferred. Also included are the processes for the preparation of such compound; rodenticidal compositions containing them; and a method for controlling rodents by applying such a composition.

  具有一般分子式的血液抗凝特性的化合物： 其中 Z 代表卤素原子，最好是氯原子，n 是 0、1 或 2，R4 代表 (1) 由直接或间接连接到四氢萘环上的亚苯基基团组成的基团，该基团在对位上(相对于这种连接) 具有一个其旋转体积基本上不超过苯基旋转体积的抽电子原子或基团，该原子或基团与所述亚苯基基团一起形成可极化结构，或 (2) 选自以下的基团： 或 (3) 由直接连接到四氢萘环上的亚苯基基团组成的基团，该基团在对位（相对于该连接）上直接或通过氧和/或亚甲基连接有取代的呋喃基或噻吩基，所述呋喃基或噻吩基在与呋喃基或噻吩基一起形成可极化结构的位置上具有作为取代基的这样的电子撤回原子或基团。优选 (1) 型化合物，其中 R4 含有两个亚苯基，这两个亚苯基通过由一个或多个亚甲基和至少一个氧原子或硫原子组成的脂肪族链基本线性连接。 此外，还包括制备此类化合物的工艺；含有此类化合物的杀鼠组合物；以及通过施用此类组合物控制啮齿动物的方法。
• Identification and optimization of biphenyl derivatives as novel tubulin inhibitors targeting colchicine-binding site overcoming multidrug resistance
  作者：Bao Cheng、Guirong Zhu、Linghua Meng、Guolin Wu、Qin Chen、Shengming Ma

  DOI：10.1016/j.ejmech.2021.113930

  日期：2022.1

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