CN109970703A - Preparation method and application of 1,3-heterocyclic substituted aromatic ketones - Google Patents
Preparation method and application of 1,3-heterocyclic substituted aromatic ketones Download PDFInfo
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- 150000008365 aromatic ketones Chemical class 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 36
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims abstract description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 13
- 229960003424 phenylacetic acid Drugs 0.000 claims abstract description 13
- 239000003279 phenylacetic acid Substances 0.000 claims abstract description 13
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 239000000463 material Substances 0.000 claims abstract description 8
- 229960000549 4-dimethylaminophenol Drugs 0.000 claims abstract description 5
- 238000004440 column chromatography Methods 0.000 claims abstract description 5
- 239000003472 antidiabetic agent Substances 0.000 claims abstract description 4
- 239000004020 conductor Substances 0.000 claims abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 4
- 239000003480 eluent Substances 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 239000000047 product Substances 0.000 claims 2
- 239000000706 filtrate Substances 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 229940126904 hypoglycaemic agent Drugs 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 230000005693 optoelectronics Effects 0.000 abstract description 4
- 238000011031 large-scale manufacturing process Methods 0.000 abstract description 3
- 238000001308 synthesis method Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N N,N′-Dicyclohexylcarbodiimide Substances C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract 1
- 239000012467 final product Substances 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- QOYNPSVOHUTODU-UHFFFAOYSA-N 2,4-dimethyl-2,4-di(thiophen-3-yl)pentan-3-one Chemical compound C1=CSC=C1C(C)(C)C(=O)C(C)(C)C=1C=CSC=1 QOYNPSVOHUTODU-UHFFFAOYSA-N 0.000 description 1
- RCNOGGGBSSVMAS-UHFFFAOYSA-N 2-thiophen-3-ylacetic acid Chemical compound OC(=O)CC=1C=CSC=1 RCNOGGGBSSVMAS-UHFFFAOYSA-N 0.000 description 1
- -1 3-(2,3-Dimethyl-3-(thiophen-3-yl)but-2-yl)thiophene Chemical compound 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000012229 microporous material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
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- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1,3‑杂环取代芳香酮的制备方法及应用，属于医药技术及光电材料领域。本发明以杂环取代的芳香苯乙酸为原料和DCC和DMAP在二氯甲烷体系反应得到化合物，化学物使用柱层析提纯得到最终产品，该产品可以用在降糖药和光电结晶导体材料的制备。本发明使用杂环取代的芳香苯乙酸反应制备1,3‑杂环取代芳香酮；反应操作简单易行，在温和反应条件下进行。本发明提供的合成方法简单易行、科学合理、绿色环保、经济实用，适合规模化生产。The preparation method and application of 1,3-heterocyclic substituted aromatic ketone belong to the fields of medical technology and optoelectronic materials. In the present invention, the heterocyclic substituted aromatic phenylacetic acid is used as the raw material, and DCC and DMAP are reacted in the dichloromethane system to obtain the compound, and the chemical substance is purified by column chromatography to obtain the final product, which can be used in hypoglycemic drugs and photoelectric crystalline conductor materials. preparation. The present invention uses heterocyclic substituted aromatic phenylacetic acid to react to prepare 1,3-heterocyclic substituted aromatic ketone; the reaction operation is simple and feasible, and is carried out under mild reaction conditions. The synthesis method provided by the invention is simple, feasible, scientific and reasonable, environmentally friendly, economical and practical, and is suitable for large-scale production.
Description
技术领域technical field
本发明涉及医药技术及光电材料领域，主要涉及1,3-杂环取代芳香酮的制备方法及应用。The invention relates to the fields of medical technology and photoelectric materials, and mainly relates to a preparation method and application of 1,3-heterocyclic substituted aromatic ketones.
背景技术Background technique
1,3-杂环取代芳香酮由于其独特的分子结构、光电特性以及它们在p-电子材料上的应用，使其在微孔材料、结晶光电导体、合成石墨烯片段等方面的应用越来越广泛。同时，1,3-杂环取代芳香酮可作为一种廉价的前体，快速有效地制备相对复杂的构造物，所以在药物合成方面也有重要应用。基于此，本领域需要更加简便、绿色、经济的方法来合成1,3-杂环取代芳香酮。本发明使用杂环取代的芳香苯乙酸的反应制备1,3-杂环取代芳香酮。反应操作简单易行，在温和反应条件下进行。本发明提供的合成方法简单易行、科学合理、绿色环保、经济实用，适合规模化生产。1,3-heterocyclic substituted aromatic ketones are increasingly used in microporous materials, crystalline photoconductors, and synthetic graphene fragments due to their unique molecular structure, optoelectronic properties, and their application in p-electronic materials. more extensive. At the same time, 1,3-heterocyclic substituted aromatic ketones can be used as a cheap precursor to prepare relatively complex structures quickly and efficiently, so they also have important applications in drug synthesis. Based on this, a more convenient, green and economical method is needed in the field to synthesize 1,3-heterocyclic substituted aromatic ketones. The invention uses the reaction of aromatic phenylacetic acid substituted by heterocycle to prepare 1,3-heterocycle substituted aromatic ketone. The reaction operation is simple and easy, and is carried out under mild reaction conditions. The synthesis method provided by the invention is simple, feasible, scientific and reasonable, environmentally friendly, economical and practical, and suitable for large-scale production.
发明内容Contents of the invention
为弥补现有技术的不足，本发明提供了操作简单易行、温和条件下合成1,3-杂环取代芳香酮的方法。In order to make up for the deficiencies of the prior art, the invention provides a method for synthesizing 1,3-heterocyclic substituted aromatic ketones with simple operation and mild conditions.
本发明采用如下技术方案：1,3-杂环取代芳香酮，具有如式Ⅰ所示的结构：The present invention adopts the following technical scheme: 1,3-heterocyclic substituted aromatic ketone has the structure shown in formula I:
本发明的目的是请求保护上述1,3-杂环取代芳香酮的制备方法，即：将DCC(N,N'-二环己基碳酰亚胺)和DMAP(4-二甲氨基吡啶)按照摩尔比为1～10：1～2加入到圆底烧瓶中，并加入干燥的二氯甲烷(1mmol:(2～5mL))至搅拌均匀。将杂环取代的芳香苯乙酸(摩尔数与DCC相等)溶解在(1mmol:(4～8mL))干燥的二氯甲烷溶液中，采用恒压滴液漏斗滴加至反应液中，在温度为20～30℃反应24-72h，随着反应的进行溶液的颜色变为橙色，过滤出沉淀，之后进行旋蒸。采用柱层析分离得到化合物(洗脱剂为乙酸乙酯：石油醚＝1:5)。The purpose of the present invention is to claim the preparation method of the above-mentioned 1,3-heterocyclic substituted aromatic ketone, that is: DCC (N, N'-dicyclohexylcarboimide) and DMAP (4-dimethylaminopyridine) according to The molar ratio is 1-10: 1-2 was added to the round bottom flask, and dry dichloromethane (1mmol:(2-5mL)) was added until the mixture was evenly stirred. Dissolve heterocyclic substituted aromatic phenylacetic acid (the number of moles of which is equal to DCC) in (1mmol: (4-8mL)) dry dichloromethane solution, and add it dropwise to the reaction solution using a constant pressure dropping funnel. React at 20-30°C for 24-72 hours, the color of the solution turns orange as the reaction progresses, filter out the precipitate, and then perform rotary evaporation. The compound was separated by column chromatography (eluent: ethyl acetate:petroleum ether=1:5).
所述的二氯甲烷的体积数均是以杂环取代的芳香苯乙酸的摩尔量为标准的。The volume numbers of the dichloromethane are all based on the molar weight of heterocyclic substituted aromatic phenylacetic acid.
优选的，所述的杂环取代的芳香苯乙酸为： Preferably, described heterocyclic substituted aromatic phenylacetic acid is:
本发明同时请求保护上述1,3-杂环取代芳香酮在药物制备及光电材料领域上的应用。The present invention also claims the application of the above-mentioned 1,3-heterocyclic substituted aromatic ketone in the fields of drug preparation and photoelectric materials.
比如用于降糖药中间体或光电结晶导体材料的制备。For example, for the intermediates of hypoglycemic drugs or optoelectronic crystalline conductor material preparation.
与现有技术相比，本发明的有益效果是：Compared with prior art, the beneficial effect of the present invention is:
本发明使用杂环取代的芳香苯乙酸反应制备1,3-杂环取代芳香酮；反应操作简单易行，在温和反应条件下进行。本发明提供的合成方法简单易行、科学合理、绿色环保、经济实用，适合规模化生产。The invention prepares 1,3-heterocyclic substituted aromatic ketone by reacting heterocyclic substituted aromatic phenylacetic acid; the reaction operation is simple and easy, and is carried out under mild reaction conditions. The synthesis method provided by the invention is simple, feasible, scientific and reasonable, environmentally friendly, economical and practical, and suitable for large-scale production.
具体实施方式Detailed ways
下面通过具体实施例详述本发明，但不限制本发明的保护范围。如无特殊说明，本发明所采用的实验方法均为常规方法，所用实验器材、材料、试剂等均可从化学公司购买。The present invention is described in detail below through specific examples, but the protection scope of the present invention is not limited. Unless otherwise specified, the experimental methods used in the present invention are conventional methods, and the experimental equipment, materials, reagents, etc. used can be purchased from chemical companies.
实施例1Example 1
取一个100mL圆底烧瓶，将DCC(1.0320g,5mmol)和DMAP(0.1222g,1mmol)加入10mL干燥的的二氯甲烷中，搅拌至全部溶解。将3-噻吩乙酸(0.7109g,5mmol)溶解至20mL干燥的二氯甲烷中，然后用恒压滴液漏斗缓慢滴加至上述溶液中。搅拌24-72h。旋干，然后经柱色谱分离(洗脱剂为乙酸乙酯：石油醚:＝1:5)从而得到目标化合物。表征如下：Take a 100mL round bottom flask, add DCC (1.0320g, 5mmol) and DMAP (0.1222g, 1mmol) into 10mL of dry dichloromethane, stir until they are all dissolved. 3-thiopheneacetic acid (0.7109 g, 5 mmol) was dissolved in 20 mL of dry dichloromethane, and then slowly added dropwise to the above solution using a constant pressure dropping funnel. Stir for 24-72h. Spin-dried, and then separated by column chromatography (eluent: ethyl acetate:petroleum ether:=1:5) to obtain the target compound. Characterized as follows:
1,3-噻吩丙酮：收率：56％。1H NMR(500MHz,CDCl3)δ7.19-7.13(m,2H),6.94(t,J＝6.4Hz,2H),6.80(dd,J＝4.9,0.9Hz,2H),3.63(s,4H).1,3-thiopheneacetone: Yield: 56%. 1 H NMR (500MHz, CDCl 3 ) δ7.19-7.13(m, 2H), 6.94(t, J=6.4Hz, 2H), 6.80(dd, J=4.9, 0.9Hz, 2H), 3.63(s, 4H).
实施例2Example 2
降糖药中间体的应用Application of intermediates of hypoglycemic drugs
将溶解在15mL无水THF中的1,3-噻吩丙酮(0.350g,1.57mmol)滴加到冷却的含有氢化钾(0.5g,12.2mmol)的THF(30mL,0℃)的溶液中。将碘甲烷(0.4mL,6.4mmol)逐滴加入到黄色悬浮液中并搅拌至室温。待悬浮液变白，然后回流直至观察到悬浮液变为橙色，然后将悬浮液冷却至0℃，滴加额外量的碘甲烷(0.15mL，2.4mmol)，然后用水和乙醚萃取。醚层用硫酸镁干燥并减压蒸发。通过柱色谱(二氧化硅,CH3COOC2H5＝10％,己烷＝90％)纯化残余物，得到白色结晶粉末。表征如下：1,3-Thienacetone (0.350 g, 1.57 mmol) dissolved in 15 mL of anhydrous THF was added dropwise to a cooled solution of potassium hydride (0.5 g, 12.2 mmol) in THF (30 mL, 0 °C). Iodomethane (0.4 mL, 6.4 mmol) was added dropwise to the yellow suspension and stirred to room temperature. After the suspension turned white, it was then refluxed until an orange color was observed, then the suspension was cooled to 0 °C, an additional amount of iodomethane (0.15 mL, 2.4 mmol) was added dropwise, and extracted with water and ether. The ether layer was dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica, CH3COOC2H5=10%, hexane=90%) to obtain a white crystalline powder. Characterized as follows:
2,4-二甲基-2,4-二(噻吩-3-基)戊-3-酮：收率：90％；熔点：76-78℃。1HNMR(500MHz,CDCl3)δ7.17(dd,J＝4.96Hz,1H),6.84(d,J＝2.9Hz,1H),6.76(dd,J＝4.96Hz,1H),1.36(s,6H)。2,4-Dimethyl-2,4-bis(thiophen-3-yl)pentan-3-one: Yield: 90%; Melting point: 76-78°C. 1 HNMR (500MHz, CDCl 3 ) δ7.17(dd, J=4.96Hz, 1H), 6.84(d, J=2.9Hz, 1H), 6.76(dd, J=4.96Hz, 1H), 1.36(s, 6H).
实施例3Example 3
光电材料的应用Application of optoelectronic materials
向1,3-噻吩丙酮(0.04g，0.14mmol)的丙酮(2mL)溶液中一次性加入10mL水/SDS溶液(2.5mM)。在搅拌的同时将空气吹到反应小瓶上，直至获得总体积为6mL的空气。加入额外的2mL水使总体积为8mL。将乳白色悬浮液置于距离中压Hg海诺威灯的距离(～10cm)处并搅拌，同时在光解室内保持4个恒定温度(约25℃)。在照射过程中，在不同时间取出少量各样品，并通过GC，NMR和X-RPD分析。照射在12小时后停止，然后过滤黄色沉淀，得到目标化合物。表征如下：To a solution of 1,3-thiopheneacetone (0.04 g, 0.14 mmol) in acetone (2 mL) was added 10 mL of a water/SDS solution (2.5 mM) in one portion. Air was blown over the reaction vial while stirring until a total volume of 6 mL of air was obtained. An additional 2 mL of water was added to bring the total volume to 8 mL. The milky white suspension was placed at a distance (~10 cm) from a medium pressure Hg Hanovia lamp and stirred while maintaining 4 constant temperatures (about 25°C) in the photolysis chamber. During irradiation, a small amount of each sample was taken at different times and analyzed by GC, NMR and X-RPD. Irradiation was stopped after 12 hours, and the yellow precipitate was filtered to yield the title compound. Characterized as follows:
3-(2,3-二甲基-3-(噻吩-3-基)丁-2-基)噻吩：收率：70％；熔点：125-128℃。1HNMR(500HMz,CDCl3)δ7.14(dd,J＝3.0,4.98Hz,1H),6.79(dd,J＝3.0Hz,1H),6.77(dd,J＝4.98Hz,1H)1.34(s,6H)。3-(2,3-Dimethyl-3-(thiophen-3-yl)but-2-yl)thiophene: Yield: 70%; Melting point: 125-128°C. 1 HNMR (500HMz, CDCl3) δ7.14 (dd, J = 3.0, 4.98Hz, 1H), 6.79 (dd, J = 3.0Hz, 1H), 6.77 (dd, J = 4.98Hz, 1H) 1.34 (s, 6H).
以上所述，仅为本发明创造较佳的具体实施方式，但本发明创造的保护范围并不局限于此，任何熟悉本技术领域的技术人员在本发明创造披露的技术范围内，根据本发明创造的技术方案及其发明构思加以等同替换或改变，都应涵盖在本发明创造的保护范围之内。The above is only a preferred embodiment of the present invention, but the scope of protection of the present invention is not limited thereto, any person familiar with the technical field within the technical scope of the disclosure of the present invention, according to the present invention Any equivalent replacement or change of the created technical solution and its inventive concept shall be covered within the scope of protection of the present invention.
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| CN114426533A (en) * | 2021-12-23 | 2022-05-03 | 玉林师范学院 | A kind of method and application of ruthenium-catalyzed preparation of polyaryl-substituted benzothiophene |
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| CN114426533A (en) * | 2021-12-23 | 2022-05-03 | 玉林师范学院 | A kind of method and application of ruthenium-catalyzed preparation of polyaryl-substituted benzothiophene |
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