5'-Chlor-2'-hydroxy-4-methoxy-chalcon | 1226-09-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 5'-Chlor-2'-hydroxy-4-methoxy-chalcon
• 英文别名: 5'-Chlor-4-methoxy-2'-hydroxy-chalkon；1-(5-chloro-2-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 1226-09-1
• 化学式: C₁₆H₁₃ClO₃
• 分子量: 288.73
• InChiKey: WGKASIDCKLLXKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5'-Chlor-2'-hydroxy-4-methoxy-chalcon 在 sodium tetrahydroborate 作用下， 以 异丙醇 为溶剂， 生成 6-Chloro-2-(4-methoxy-phenyl)-2H-chromene
  参考文献：
  名称：

  An unexpected rearrangement-hydration reaction sequence of 2H-chromenes to dihydrochalcones under catalysis of HAuCl4

  摘要：

  2-Aryl-2H-chromenes in aqueous DCM medium under catalysis of HAuCl4 are converted into 3-(2-hydroxyaryl)-1-arylpropan-1-ones through hydration-rearrangement reaction sequence in very good yield. The key step probably involves the [1,5] hydride shift followed by the hydrolysis under the reaction condition. The notable advantages of this method are operational simplicity and ease of isolation of products and also provide a pathway to convert the chalcone into DHCs with the transposition of carbonyl group. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.117
• 作为产物：
  描述：

  乙酸-4-氯苯酯 在 sodium hydroxide 、 三氯化铝 作用下， 生成 5'-Chlor-2'-hydroxy-4-methoxy-chalcon
  参考文献：
  名称：

  Chlor-hydroxychalkone

  摘要：

  DOI：

  10.1007/bf00904270

文献信息

• IODINE CATALYZED CASCADE SYNTHESIS OF FLAVONE DERIVATIVES FROM 2'-ALLYLOXY-α, β-DIBROMOCHALCONES
  作者：BEENA R NAWGHARE、SUNIL V GAIKWAD、ABDUL RAHEEM、PRADEEP D LOKHANDE

  DOI：10.4067/s0717-97072014000100009

  日期：——

  Synthesis of flavones from 2'-allyloxy-α, β-dibromochalcones has been described. The iodine induced oxidative cyclization of 2'-allyloxy-α, β-dibromochalcones results into the formation of 3-bromoflavanones which ultimately gives flavones. Dehydrobromination of 3-bromoflavanone to give flavone is the preferred reaction over dehydrogenation. 6 3-Bromoflavones are used in drugs and for synthesis of alkylated

  已经描述了由2'-烯丙氧基-α，β-二溴代查耳酮合成黄酮。碘诱导的2'-烯丙氧基-α，β-二溴代邻苯二甲醛的氧化环化作用导致形成3-溴代黄酮，最终产生黄酮。3-溴黄酮的脱氢溴化反应得到黄酮是优于脱氢的优选反应。6 3-溴代黄酮用于药物和烷基化和芳基化的黄酮的合成。观察到具有溴取代基的各种查耳酮，黄酮和黄烷酮具有抗结核活性。7 6-溴黄酮已显示出对中心苯并二氮杂receptor受体的结合亲和力和对小鼠的抗焦虑作用。8个3-异黄酮用于合成类黄酮。9脱溴1 已经报道了在烯烃存在下通过使用四（二甲基氨基）乙烯（TDAE）形成2-双（溴甲基）芳烃，并且催化量的碘。10作为先前研究11的延伸，我们对2'-烯丙氧基-α，β-二溴代查耳酮的合成感兴趣，该合成法通过在二甲基亚砜试剂中使用碘来产生相应的3-溴代黄酮。在较早的工作中，当2'-烯丙氧基查耳酮与DMSO-1 2试剂反应时，烯丙基被平滑除去，然后环化
• Iodine-mediated direct synthesis of 3-iodoflavones
  作者：Avinash M. Patil、Dayanand A. Kamble、Pradeep D. Lokhande

  DOI：10.1080/00397911.2018.1440601

  日期：2018.6.3

  ABSTRACT Molecular iodine has been used for the regioselective, one pot, direct synthesis of 3-iodoflavones from 2′-allyloxy chalcones, 2′-hydroxy chalcones and flavones. Allyl deprotection, cyclization dehydrogenation and α-iodination of 2′-allyloxychalcones has been achieved in a single step to offer 3-iodoflavones. GRAPHICAL ABSTRACT

  摘要 分子碘已被用于区域选择性、一锅法、直接从 2'-烯丙氧基查耳酮、2'-羟基查耳酮和黄酮合成 3-碘黄酮。2'-烯丙氧基查耳酮的烯丙基脱保护、环化脱氢和 α-碘化已在一步中实现，以提供 3-碘黄酮。图形概要
• Synthesis of 5-aryl-2-piperidino-5H-chromeno[3,4-c]pyridine-1-carbonitriles
  作者：M. Venkati、S. Satyanarayana Reddy、G. Y. S. K. Swamy、K. Ravikumar、G. L. David Krupadanam

  DOI：10.3998/ark.5550190.0013.632

  日期：——

  Chloro-2-aryl-2H-3-chromenecarbaldehydes 3a-g on reaction with malononitrile in ethanol in the presence of piperidine gave 5-aryl-2-piperidino-5H-chromeno(3,4-c)pyridine-1-carbonitriles 4a-g in good yields.

  在哌啶存在下，氯-2-芳基-2H-3-色烯甲醛 3a-g 在乙醇中与丙二腈反应，得到 5-芳基-2-哌啶基-5H-色基（3,4-c）吡啶-1-腈4a -g 收益良好。
• Absorption and Fluorescent Studies of 3-Hydroxychromones
  作者：Radhika Khanna、Ramesh Kumar、Aarti Dalal、Ramesh C. Kamboj

  DOI：10.1007/s10895-015-1623-0

  日期：2015.9

  The synthesis and spectral studies of variously substituted 3-hydroxychromones have been carried out. A key relationship between the structural motif of synthesized 3-hydroxychromones (3-HCs) and their fluorescent properties was found. The chromones substituted with electron-donating group at 4′-position expressed the red shift of the N* and T* band and also exhibited the increased fluorescent intensity ratio while the chromones with electron-withdrawing group showed the blue shift of the N* and T* band. Therefore, these 3-HCs may behave as the possible fluorescent probes.

  已经进行了各种取代的3-羟基色酮的合成和光谱研究。发现了合成的 3-羟基色酮 (3-HC) 的结构基序与其荧光特性之间的关键关系。 4'位被给电子基团取代的色酮表现出N*和T*带的红移，并且荧光强度比增加，而带有吸电子基团的色酮则表现出N*和T*带的蓝移。 T*带。因此，这些 3-HC 可能充当可能的荧光探针。
• Pyrazoline and Hydrazone Derivatives as Potent Membrane Stabilizer and Antioxidant Compounds
  作者：Begum Evranos Aksoz、Sezen Yilmaz Sarialtın、Tulay Coban

  DOI：10.1007/s11094-022-02624-z

  日期：2022.5

  Membrane-stabilizing and antioxidant activities of twenty six pyrazoline and hydrazone derivatives were investigated. Antioxidant activity of these compounds was examined by using in vitro 2,2-azino-bis(3-ethyl-benzothiazoline-6-sulphonic acid) (ABTS) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging assays. Butylated hydroxytoluene (BHT) was used as DPPH• free radical scavenger standard, and trolox was used as ABTS•+ free radical scavenger standard. Some compounds (D13, D16 and D22) showed good antioxidant activity. All compounds were found to exhibit better membrane stabilizing activity than the reference acetylsalicylic acid.

  研究了 26 种吡唑啉和腙衍生物的膜稳定和抗氧化活性。这些化合物的抗氧化活性是通过体外 2,2-氮基-双（3-乙基-苯并噻唑啉-6-磺酸）（ABTS）和 2,2-二苯基-1-苦基肼（DPPH）自由基清除试验进行检测的。丁基羟基甲苯（BHT）用作 DPPH-自由基清除剂标准，三氧化锡用作 ABTS-+ 自由基清除剂标准。一些化合物（D13、D16 和 D22）显示出良好的抗氧化活性。所有化合物的膜稳定活性均优于参考物质乙酰水杨酸。