4-(5-chloro-2-hydroxy-phenyl)-but-3-en-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-(5-chloro-2-hydroxy-phenyl)-but-3-en-2-one
• 英文别名: (E)-4-(5-chloro-2-hydroxyphenyl)but-3-en-2-one；trans-5-Chlorsalicylenaceton；4-(5-chloro-2-hydroxyphenyl)but-3-(E)-en-2-one；4-(5-Chloro-2-hydroxyphenyl)but-3-en-2-one
• 化学式: C₁₀H₉ClO₂
• 分子量: 196.633
• InChiKey: JJJFJYKYPLNQEB-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  反式肉桂醛 、 4-(5-chloro-2-hydroxy-phenyl)-but-3-en-2-one 在 四氢吡咯 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以73%的产率得到
  参考文献：
  名称：

  Dually activated Michael-Michael-acetalization cascade: facile and highly diastereoselective construction of tetrahydro-6-hydroxyl-6H-benzo[c]chromen-9-one polycyclic scaffold

  摘要：

  A Michael-Michael-acetalization cascade between 4-(2-hydroxyphenyl)but-3-en-2-ones and alpha,beta-unsaturated aldehydes via a novel dual activation mode promoted by pyrrolidine was successfully established. Consequently, various novel tetrahydro-6-hydroxyl-6H-benzo[c]chromen-9-one derivatives were prepared in excellent diastereoselectivities and moderate to good yields. Further diverse modification of the resulting tricyclic scaffolds provided a facile pathway to achieve a variety of tetrahydro-6-hydroxyl-6H-benzo[c]chromen-9-one analogs. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.014
• 作为产物：
  描述：

  丙酮 、 5-氯代水杨醛 在 potassium carbonate 作用下， 生成 4-(5-chloro-2-hydroxy-phenyl)-but-3-en-2-one
  参考文献：
  名称：

  An Atom-Economical Approach to the Synthesis of Potentially Bioactive 2H-Chromenes via CuI-Catalyzed Reactions of Alkyl/Aryl-(E)-(o-Propar­gyloxy)styryl Ketones

  摘要：

  A series of potentially bioactive 2H-chromenes have been synthesized in good yields (60-82%) via CuI-catalyzed reactions of alkyl/aryl-(E)-(o-propargyloxy)styryl ketones in an atom-economical approach.

  DOI：

  10.1055/s-0031-1290769

文献信息

• Asymmetric Dearomative Cascade Multiple Functionalizations of Activated <i>N</i>-Alkylpyridinium and <i>N</i>-Alkylquinolinium Salts
  作者：Xue Song、Ru-Jie Yan、Wei Du、Ying-Chun Chen

  DOI：10.1021/acs.orglett.0c02828

  日期：2020.10.2

  An enantioselective cascade reaction of N-alkylpyridinium and -quinolinium salts with o-hydroxybenzylideneacetones to access fused polyheterocycles through cross dienamine-mediated addition followed by trapping of the dearomatized enamine-type intermediates and aminal formation has been developed. A cascade assembly of N-benzyl-4-methylpyridinium salt and cyclic 2,4-dienones is further disclosed to

  已开发出N-烷基吡啶鎓盐和-喹啉鎓盐与邻羟基苄叉基丙酮的对映选择性级联反应，通过交叉二烯胺介导的加成反应，然后捕获脱芳族化的烯胺型中间体和缩醛形成，从而进入稠合多杂环。还公开了N-苄基-4-甲基吡啶盐和环状2，4-二壬烯的级联组装，以通过重复的脱芳香化作用和芳构化活化作用给出桥连的骨架。
• Cascade Nucleophilic Addition−Cyclic Michael Addition of Arynes and Phenols/Anilines Bearing Ortho α,β-Unsaturated Groups: Facile Synthesis of 9-Functionalized Xanthenes/Acridines
  作者：Xian Huang、Tiexin Zhang

  DOI：10.1021/jo902311a

  日期：2010.1.15

  A facile synthesis of xanthenes and acridines based on a cascade nucleophilic addition−cyclic Michael addition process of arynes and phenols/anilines substituted with α,β-unsaturated groups at the ortho positions is described. The reaction has also been successfully extended to the synthesis of 9-spiro-xanthene and acridine derivatives with potential biochemical interest.

  描述了基于芳烃和邻位被α，β-不饱和基团取代的苯酚/苯胺的级联亲核加成-迈克尔环加成反应的黄嘌呤和a啶的简便合成方法。该反应也已成功地扩展到具有潜在生物化学意义的9-螺并氧杂蒽和a啶衍生物的合成。
• COMPOUNDS
  申请人：Boyle Jessica

  公开号：US20080161288A1

  公开（公告）日：2008-07-03

  Compounds of formula (I) and pharmaceutically acceptable salts thereof are agonists at the beta-2 adrenoceptor. They are useful as feed additives for livestock animals.

  化学式为（I）的化合物及其药学上可接受的盐是β-2肾上腺素受体激动剂。它们可用作家畜饲料添加剂。
• Tricyclic cyanoguanidines: synthesis, site of action and insecticidal activity of a novel class of reversible acetylcholinesterase inhibitors
  作者：Bruce L. Finkelstein、Eric A. Benner、Maura C. Hendrixson、Kevin T. Kranis、James J. Rauh、Maya R. Sethuraman、Stephen F. McCann

  DOI：10.1016/s0968-0896(01)00326-1

  日期：2002.3

  Bridged-tricyclic cyanoguanidines 1 were found to be active as insecticides. The preparation and structure-activity relationships of oxacyclic (X=O) and carbocyclic (X=CH2) analogues of 1 is described. Compounds 1 were found to inhibit acetylcholinesterase with IC50 values comparable to the organophosphate Paraoxon. Unlike organophosphates. cyanoguanidines 1 were shown to reversibly bind acetylcholinesterase. This mode of action is shared by the structurally-related natural product Huperzine A. (C) 2002 Elsevier Science Ltd. All rights reserved.
• GUPTA R. K.; GEORGE M. V., INDIAN J. CHEM., 1977, B15, NO 3,
  作者：GUPTA R. K.、 GEORGE M. V.

  DOI：——

  日期：——