1-(3-氯苯基)戊烷-1,4-二酮 | 735276-43-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(3-氯苯基)戊烷-1,4-二酮
• 英文名称: 1-(3-chlorophenyl)pentane-1,4-dione
• CAS: 735276-43-4
• 化学式: C₁₁H₁₁ClO₂
• 分子量: 210.66
• InChiKey: URWAEVRPAMPJHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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-(3-氯苯基)戊烷-1,4-二酮 在 溶剂黄146 、 gadolinium(III) trifluoromethanesulfonate 作用下， 以 水 、 乙腈 为溶剂， 反应 6.5h， 生成 (5R)-5-(azidomethyl)-3-(4-(4-((5-(3-chlorophenyl)-1-(2-fluorophenyl)-2-methyl-1H-pyrrol-3-yl)methyl)piperazin-1-yl)-3-fluorophenyl)oxazolidin-2-one
  参考文献：
  名称：

  Anti-tubercular agents. Part 7: A new class of diarylpyrrole–oxazolidinone conjugates as antimycobacterial agents

  摘要：

  In an effort to discover new anti-tubercular agents, a series of new diarylpyrrole oxazolidinone conjugates have been designed and synthesized. The anti-tubercular activity of these new conjugates (4a-n and 5a-d) against Mycobacterium tuberculosis H(37)Rv and drug resistance strains such as M. tuberculosis Rif(R) and M. tuberculosis XDR are discussed, wherein compound 4i has been found to be the most potent amongst the series. MTT assay was performed on the active conjugates of the series (4b-f, 4i and 5c) against mouse macrophage (J-774) cells to evaluate cytotoxic effects and selective index values. In addition, these conjugates (4a-n and 5a-d) are also tested against a panel of Gram-positive and Gram-negative bacterial strains. The docking studies have been carried out to provide some insight into the mechanism of action for this class of compounds. (C) 2013 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2013.03.027
• 作为产物：
  描述：

  3-氯苯乙酮 在 溴苯 、 silver fluoride 、 三乙胺 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 36.17h， 生成 1-(3-氯苯基)戊烷-1,4-二酮
  参考文献：
  名称：

  硅基烯醇醚的银催化控制分子间交叉偶联：可扩展地获得 1,4-二酮

  摘要：

  公开了一种用于甲硅烷基烯醇化物的银催化受控分子间交叉偶联的方案。该协议显示出良好的官能团耐受性，并允许有效制备一系列合成有用的 1,4-二酮。初步的机理研究表明，该反应通过一个单电子过程进行，其中涉及自由基物质，其中 PhBr 充当氧化剂。

  DOI：

  10.1021/acs.orglett.2c01477

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。
• A fluorescent target-guided Paal–Knorr reaction
  作者：Sachin B. Wagh、Vladimir Maslivetc、James J. La Clair、Alexander Kornienko

  DOI：10.1039/d0ra06962k

  日期：——

  It has become increasingly apparent that high-diversity chemical reactions play a significant role in the discovery of bioactive small molecules. Here, we describe an expanse of this paradigm, combining a ‘target-guided synthesis’ concept with Paal–Knorr chemistry applied to the preparation of fluorescent ligands for human prostaglandin-endoperoxide synthase (COX-2).

  越来越明显的是，高度多样性的化学反应在发现生物活性小分子方面发挥着重要作用。在这里，我们描述了这种范式的扩展，将“目标引导合成”概念与用于制备人前列腺素内过氧化物合酶 (COX-2) 的荧光配体的 Paal-Knorr 化学相结合。
• New synthesis of 1,4-diketones via rhodium-catalysed 1,4 carbonylative addition of arylboronic acids to α,β-unsaturated ketones
  作者：Mathieu Sauthier、Yves Castanet、André Mortreux

  DOI：10.1039/b403415e

  日期：——

  The reaction of various arylboronic acids with alpha,beta-unsaturated ketones under CO pressure and in the presence of rhodium catalyst yields 1,4-diketones.

  各种芳基硼酸与α，β-不饱和酮在CO压力下，在铑催化剂的存在下反应，生成1，4-二酮。
• 1,4-Carbonylative addition of arylboronic acids to methyl vinyl ketone: a new synthetic tool for rapid furan and pyrrole synthesis
  作者：Hélène Chochois、Mathieu Sauthier、Eddy Maerten、Yves Castanet、André Mortreux

  DOI：10.1016/j.tet.2006.09.035

  日期：2006.12

  The rhodium catalysed 1,4-carbonylative addition of arylboronic acids to methyl vinyl ketone under carbon monoxide pressure was studied. High yields of 1,4-diketones were obtained using a catalytic system formed from Rh(COD)2BF4 (COD=1,5-cyclooctadiene) and triphenylphosphine even at very low catalyst loading (0.02 mol %). A short synthetic procedure combining this carbonylation reaction with a subsequent

  研究了一氧化碳压力下铑在甲基乙烯基酮上铑催化的1，4-羰基芳基硼酸加成反应。使用由Rh（COD）2 BF 4（COD = 1,5-环辛二烯）和三苯膦形成的催化体系，即使在非常低的催化剂负载量（0.02 mol％）下也能获得高产率的1,4-二酮。将该羰基化反应与随后的环化步骤结合起来的简短合成程序提供了吡咯或呋喃。
• 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.