1-(2-bromo-phenyl)-pentane-1,4-dione | 159448-53-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-bromo-phenyl)-pentane-1,4-dione
• 英文别名: 1-(2-Bromophenyl)-1,4-pentanedione；1-(2-bromophenyl)pentane-1,4-dione
• CAS: 159448-53-0
• 化学式: C₁₁H₁₁BrO₂
• 分子量: 255.111
• InChiKey: AFXCEAJNYLFKDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-bromo-phenyl)-pentane-1,4-dione 在 正丁基锂 、 4 A molecular sieve 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 16.0h， 生成 2-(5-甲基-2-呋喃基)苯甲酸
  参考文献：
  名称：

  Nonpeptide Angiotensin II Receptor Antagonists. Synthesis, in vitro Activity, and Molecular Modeling Studies of N-[(Heterobiaryl)methyl]imidazoles

  摘要：

  With the aim of explaining the influence of the structural changes on the biphenylic moiety on the activity, a series of N-[(heterobiaryl)methyl]imidazoles (I), constructed on the model of DuPont compounds by replacing either the central or terminal phenyl ring with a heteroaromatic one, such as furan, thiophene, thiazole, and pyridine, was synthesized. Compared to the reference DuPont compound (EXP-7711), all the heterobiaryl derivatives showed a reduced potency both in receptor binding (rat adrenal capsular membranes) and in the functional assay (angiotensin II-induced contraction of rabbit aorta strips). The lower activity was justified by the extensive molecular modeling studies, which took into consideration the conformational and electrostatic features of several heterobiaryl derivatives. On the basis of the results obtained, it was hypothesized that the central aromatic ring of the biarylic portion works as a spacer, orienting in the right way the terminal phenyl ring, whose electronic distribution is, instead, crucial to its fitting well with a lipophilic pocket at the receptor site.

  DOI：

  10.1021/jm00049a012
• 作为产物：
  描述：

  邻溴苯甲醛 在 正丁基锂 、 苯甲酸 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 26.0h， 生成 1-(2-bromo-phenyl)-pentane-1,4-dione
  参考文献：
  名称：

  2,5-Disubstituted furans from 1,4-alkynediols

  摘要：

  1-4-Alkynediols serve as readily available starting materials for isomerisation to 1,4-diketones, which can be converted in situ into the corresponding furans by acid-catalysed dehydration. A range of 2,5-disubstituted furans was prepared using the ruthenium-based catalyst Ru(PPh3)(3)(CO)H-2 with Xantphos at 1 mol % loading. (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2007.05.069

文献信息

• Copper-Catalyzed Decarboxylative Oxyalkylation of Alkynyl Carboxylic Acids: Synthesis of γ-Diketones and γ-Ketonitriles
  作者：Yi Li、Jia-Qi Shang、Xiang-Xiang Wang、Wen-Jin Xia、Tao Yang、Yangchun Xin、Ya-Min Li

  DOI：10.1021/acs.orglett.9b00520

  日期：2019.4.5

  A novel copper-catalyzed decarboxylative oxyalkylation of alkynyl carboxylic acids with ketones and alkylnitriles via direct C(sp3)–H bond functionalization to construct new C–C bonds and C–O double bonds was developed. This transformation is featured by wide functional group compatibility and the use of readily available reagents, thus affording a general approach to γ-diketones and γ-ketonitriles

  通过直接的C（sp 3）-H键官能化来构建新的C-C键和C-O双键的新型铜催化的炔基羧酸与酮和烷基腈的脱羧氧化烷基化反应得到了发展。这种转变的特征是广泛的官能团相容性和易于使用的试剂的使用，从而为γ-二酮和γ-酮腈提供了一种通用方法。提出了一种可能的机制。
• Imidazole ethers having a II antagonist activity
  申请人：Istituto Luso Farmaco D'Italia S.p.A.

  公开号：US05538987A1

  公开（公告）日：1996-07-23

  Compounds of general formula (I) ##STR1## wherein E is O or S; R is C.sub.1 -C.sub.5 straight, branched or cyclic alkyl or C.sub.2 -C.sub.5 alkenyl; X can be H, F, Cl, Br, I, CF.sub.3 ; n is an integer 1 to 4; m is an integer 0 to 4; A and B are 5- or 6- membered aromatic carbocyclic rings optionally containing one or more heteroatoms selected from N, O, S and carrying the substituents R.sub.1, R.sub.2 and R.sub.3, respectively; R.sub.1 can be hydrogen, halogen, C.sub.1 -C.sub.4 alkoxycarbonyl, a sulfonic group or a tetrazole group of formula ##STR2## wherein R.sub.4 can be hydrogen or C.sub.1 -C.sub.5 alkyl; R.sub.2 can be hydrogen or a COOR.sub.4 group (wherein R.sub.4 is hydrogen or C.sub.1 -C.sub.5 alkyl), CN, SO.sub.3 H, PO.sub.3 H or a tetrazole group R.sub.3 ; can be a hydrogen or a moiety of formula (II) B'(R'.sub.2,R'.sub.3) (II) wherein: B.sup.1, R.sup.1.sub.2 have the same meanings reported above for B and R.sub.2, R'.sub.3 is H; with the proviso that when A is phenyl, R.sub.1 is different from H, and the pharmaceutically acceptable salts thereof.

  通式（I）的化合物##STR1##其中E为O或S；R为C.sub.1-C.sub.5直链、支链或环烷基或C.sub.2-C.sub.5烯基；X可以是H、F、Cl、Br、I、CF.sub.3；n为1到4的整数；m为0到4的整数；A和B为5-或6-成员芳香碳环，可选地含有来自N、O、S的一个或多个杂原子，并携带取代基R.sub.1、R.sub.2和R.sub.3，分别；R.sub.1可以是氢、卤素、C.sub.1-C.sub.4烷氧羰基、磺酰基或式的四唑基团##STR2##其中R.sub.4可以是氢或C.sub.1-C.sub.5烷基；R.sub.2可以是氢或COOR.sub.4基团（其中R.sub.4为氢或C.sub.1-C.sub.5烷基）、CN、SO.sub.3 H、PO.sub.3 H或四唑基团R.sub.3；可以是氢或式的一个基团（II）B'(R'.sub.2,R'.sub.3)（II）其中：B.sup.1，R.sup.1.sub.2具有上述B和R.sub.2的相同含义，R'.sub.3为H；但条件是当A为苯时，R.sub.1不同于H，及其药学上可接受的盐。
• Copper/Manganese Cocatalyzed Oxidative Coupling of Vinylarenes with Ketones
  作者：Xing-Wang Lan、Nai-Xing Wang、Wei Zhang、Jia-Long Wen、Cui-Bing Bai、Yalan Xing、Yi-He Li

  DOI：10.1021/acs.orglett.5b02116

  日期：2015.9.18

  A novel copper/manganese cocatalyzed direct oxidative coupling of terminal vinylarenes with ketones via C(sp(3))-H bond functionalization following C-C bond formation has been developed using tert-butyl hydroperoxide as the radical initiator. Various ketones underwent a free-radical addition of terminal vinylarenes to give the corresponding 1,4-dicarbonyl products with excellent regioselectivity and efficiency through one step. A possible reaction mechanism has been proposed.
• Synthesis of furans, pyrroles and pyridazines by a ruthenium-catalysed isomerisation of alkynediols and in situ cyclisation
  作者：Simon J. Pridmore、Paul A. Slatford、James E. Taylor、Michael K. Whittlesey、Jonathan M.J. Williams

  DOI：10.1016/j.tet.2009.06.108

  日期：2009.10

  Alkyne-1,4-diols are readily available substrates which are isomerised to 1,4-diketones using Ru(PPh3)(3)(CO)H-2/xantphos as a catalyst. In situ cyclisation into furans, pyrroles and pyridazines has been achieved under suitable conditions. (C) 2009 Elsevier Ltd. All rights reserved.
• Discovery of selective and potent anti-tubercular activity in arylpentane-1,4-diones
  作者：Umarani, W. A.、Sony, K. P.、Hymavathi, K. V.、Kumar, M. Murali Krishna

  DOI：10.56042/ijc.v61i4.62561

  日期：——