3-(3,4-dimethoxyphenyl)-1-(furan-2-yl)prop-2-en-1-one | 118959-61-8

• 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: 3-(3,4-dimethoxyphenyl)-1-(furan-2-yl)prop-2-en-1-one
• 英文别名: 1-(2-furyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one
• CAS: 118959-61-8
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: CCJQILWWMXROJQ-UHFFFAOYSA-N

物化性质

• 沸点：
  401.8±45.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3,4-dimethoxyphenyl)-1-(furan-2-yl)prop-2-en-1-one 在 nickel-rhenium 氢气 作用下， 以 乙醇 、 水 为溶剂， 生成 1-[2-(3,4-Dimethoxy-phenyl)-ethyl]-3,4-dihydro-pyrrolo[1,2-a]pyrazine
  参考文献：
  名称：

  Azacycloalkanes. 31. Arylalkylpyrrolo[1,2-a]pyrazines and their effects on ischemized myocardium

  摘要：

  DOI：

  10.1007/bf00763268
• 作为产物：
  描述：

  2-乙酰基呋喃 、 3,4-二甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以86%的产率得到3-(3,4-dimethoxyphenyl)-1-(furan-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  杂环查尔酮衍生物的合成及其对2,2-二苯基-1-苦基肼(DPPH)自由基的清除能力

  摘要：

  精心制备了一系列杂环杂环查耳酮衍生物，如苯环的等排体噻吩或呋喃环，并系统研究了杂环对2,2-二苯基-1-苦基肼（DPPH）自由基清除活性的影响。构效关系（SAR）分析表明，含噻吩环的查尔酮的活性高于含呋喃环的查尔酮，并且与未取代的杂环相比，杂环甲基取代基的存在对活性的影响明显相反。 , 噻吩环的 4'-甲基基团活性增加，呋喃环的 3'-甲基基团活性降低。杂环的独特等排效应（即，

  DOI：

  10.5012/bkcs.2012.33.8.2585

文献信息

• Synthesis and biological evaluation of naphthalene, furan and pyrrole based chalcones as cytotoxic and antimicrobial agents
  作者：Abhishek Budhiraja、Kanika Kadian、Mandeep Kaur、Vikas Aggarwal、Atul Garg、Sameer Sapra、Kunal Nepali、O. P. Suri、K. L. Dhar

  DOI：10.1007/s00044-011-9733-y

  日期：2012.9

  but in the present study we report the reactions of 1-acetylnaphthalene, 2-acetylfuran and 2-acetylpyrrole with aldehydes, thus getting compounds akin to chalcones. 31 analogues have been synthesised and evaluated for cytotoxic potential against PC-3, OVCAR, IMR-32 and HEP-2. Compound 9 was found to be the most cytotoxic with inhibition ranging from 72 to 88% against the cell lines employed. The synthetics

  摘要查耳酮是一种芳香族酮，可形成多种重要生物化合物（统称为查耳酮）的核心。它们显示出抗菌，抗真菌，抗肿瘤和抗炎特性，并且是类黄酮生物合成的中间体，类黄酮是植物中广泛存在的具有一系列生物活性的物质。这些联芳基丙烯酮对几种癌细胞显示出强力毒性，并在其秋水仙碱结合位点与微管蛋白相互作用。微管蛋白结合分子干扰微管的动态不稳定性，从而破坏微管，诱导细胞周期停滞在M期，形成异常纺锤体并最终导致凋亡性细胞死亡。基本上，Chalcones由C 6 –C 3 –C 6组成单位，但在本研究中，我们报道了1-乙酰基萘，2-乙酰基呋喃和2-乙酰基吡咯与醛的反应，从而得到类似于查耳酮的化合物。已合成了31种类似物，并评估了其对PC-3，OVCAR，IMR-32和HEP-2的细胞毒性。发现化合物9对细胞毒性最大，对所用细胞系的抑制作用范围为72％至88％。还评估了合成物的抗菌活性，发现化合物25最有效。 图形概要合成
• Furanyl Cyclic Ethers: Single and Double Diastereoselectivity in the Synthesis of 2,4-Di and 2,4,5-Trisubstituted Tetrahydropyrans
  作者：Dennis A. Cooper、Emma Robbins、Graham J. Tizzard、Simon J. Coles、Matthew O’Brien

  DOI：10.1021/acs.joc.6b02831

  日期：2017.4.7

  of a prochiral bis-hydroxymethyl group with the epimerization of a chiral furanyl ether in a single transformation, high levels of double diastereoselectivity have been achieved in a synthesis of 2,4,5-trisubstituted tetrahydropyrans, which proceeds under thermodynamic control.

  在一次转化中，将前手性双羟甲基的去对称化与手性呋喃基醚的差向异构化相结合，在2,4,5-三取代的四氢吡喃的合成中实现了高水平的双非对映选择性，该合成在热力学控制下进行。
• Effect of ring A and ring B substitution on the cytotoxic potential of pyrazole tethered chalcones
  作者：Kunal Nepali、Kanika Kadian、Ritu Ojha、Rajni Dhiman、Atul Garg、Gagandip Singh、Abhishek Buddhiraja、Preet Mohinder Singh Bedi、Kanaya Lal Dhar

  DOI：10.1007/s00044-011-9824-9

  日期：2012.10

  Chalcone is an aromatic ketone that forms the central core for a variety of important biological compounds, which are collectively known as chalcones. The cytotoxic potential of chalcones which consists of C-6-C-3-C-6 units gets enhanced by the incorporation of pyrazole ring as proved by our earlier studies. Thus in the present work, pyrazoles of chalcones with ring A substituted by furan, naphthalene and variety of substituted phenyl rings has been prepared and evaluated for in vitro cytotoxic activity against PC-3, OVCAR, IMR-32, HEP-2 human cancer cell lines.All the synthesized compounds were evaluated for in vitro cytotoxicity against PC-3, OVCAR, IMR-32, HEP-2 human cancer cell lines. Compound 68 was found to be the most potent showing broad spectrum of cytotoxicity against all the cell lines .
• Electrochemically Induced Ring-Opening/Friedel–Crafts Arylation of Chalcone Epoxides Catalyzed by a Triarylimidazole Redox Mediator
  作者：Nan-ning Lu、Ni-tao Zhang、Cheng-Chu Zeng、Li-Ming Hu、Seung Joon Yoo、R. Daniel Little

  DOI：10.1021/jo5022184

  日期：2015.1.16

  The indirect anodic oxidation of chalcone epoxides in the presence of electron-rich heteroarenes mediated by a triarylimidazole (Med) was investigated by cyclic voltammetry (CV) and controlled potential electrolysis. The CV results indicate that a homogeneous electron transfer between Med(center dot+) and chalcone epoxides is facilitated by an electron-rich heteroarene that serves as an arylation reagent. The preparative scale electrolysis generated epoxide-ring-opened/Friedel-Crafts arylation products in moderate to good yields. The fact that only a catalytic amount of charge was required suggests that Med(center dot+) initiates a chain reaction. In addition, overoxidation of the products is avoided even though their oxidation potential is less than that of the starting chalcone epoxides.
• One-Pot Synthesis of Polysubstituted Indolizines by an Addition/Cycloaromatization Sequence
  作者：Murat Kucukdisli、Till Opatz

  DOI：10.1021/jo400992n

  日期：2013.7.5

  Indolizines carrying various substituents in positions 5-8 were obtained from readily available 2-(1H-pyrrol-1-yl)nitriles and alpha,beta-unsaturated ketones or aldehydes in a one-pot procedure. Michael addition of the deprotonatecl aminonitriles to the acceptors followed by acid catalyzed electrophilic cyclization produces 5,6-dihydroindolizine-5-carbonitriles. From these stable intermediates, substituted indolizines were obtained via base induced dehydrocyanation.