4-(2-hydroxy-5-nitro-phenyl)-but-3-en-2-one | 125094-33-9

• 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-(2-hydroxy-5-nitro-phenyl)-but-3-en-2-one
• 英文别名: (E)-4-(2-hydroxy-5-nitrophenyl)but-3-en-2-one；4-(2-Hydroxy-5-nitro-phenyl)-but-3-en-2-on；4-(2-Hydroxy-5-nitrophenyl)but-3-en-2-one
• CAS: 125094-33-9
• 化学式: C₁₀H₉NO₄
• 分子量: 207.186
• InChiKey: FNXHBARMWISRHV-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 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：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-hydroxy-5-nitro-phenyl)-but-3-en-2-one 在 palladium on activated charcoal 哌啶 、 氢气 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 反应 1.5h， 生成 4-amino-9-methyl-8-oxa-10,12-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-trien-11-ylidene-cyanamide
  参考文献：
  名称：

  Tricyclic cyanoguanidines: synthesis, site of action and insecticidal activity of a novel class of reversible acetylcholinesterase inhibitors

  摘要：

  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.

  DOI：

  10.1016/s0968-0896(01)00326-1
• 作为产物：
  描述：

  5-硝基水杨醛 、 丙酮 在 sodium hydroxide 作用下， 生成 4-(2-hydroxy-5-nitro-phenyl)-but-3-en-2-one
  参考文献：
  名称：

  Heilbron; Whitworth, Journal of the Chemical Society, 1923, vol. 123, p. 244

  摘要：

  DOI：

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。
• Reddy; Mogilaiah; Sreenivasulu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 4, p. 362 - 364
  作者：Reddy、Mogilaiah、Sreenivasulu

  DOI：——

  日期：——
• Dually activated Michael-Michael-acetalization cascade: facile and highly diastereoselective construction of tetrahydro-6-hydroxyl-6H-benzo[c]chromen-9-one polycyclic scaffold
  作者：Jian Liu、Sai-Shuai Wen、Jing Wang、Jun-An Xiao、Shao-Jie Huang、Hua Yang

  DOI：10.1016/j.tet.2015.05.014

  日期：2015.7

  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.
• Heilbron; Whitworth, Journal of the Chemical Society, 1923, vol. 123, p. 244
  作者：Heilbron、Whitworth

  DOI：——

  日期：——
• 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.