CN115197180B - Synthesis method of 3-selenofurans compound promoted by visible light - Google Patents

Synthesis method of 3-selenofurans compound promoted by visible light Download PDF

Info

Publication number
CN115197180B
CN115197180B CN202210439256.7A CN202210439256A CN115197180B CN 115197180 B CN115197180 B CN 115197180B CN 202210439256 A CN202210439256 A CN 202210439256A CN 115197180 B CN115197180 B CN 115197180B
Authority
CN
China
Prior art keywords
reaction
formula
visible light
selenofuran
diselenide
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN202210439256.7A
Other languages
Chinese (zh)
Other versions
CN115197180A (en
Inventor
刘功清
王永浩
凌勇
周晨凡
姜有琴
张云倩
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nantong University
Original Assignee
Nantong University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nantong University filed Critical Nantong University
Priority to CN202210439256.7A priority Critical patent/CN115197180B/en
Publication of CN115197180A publication Critical patent/CN115197180A/en
Application granted granted Critical
Publication of CN115197180B publication Critical patent/CN115197180B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to the technical field of organic synthetic chemistry, in particular to a method for synthesizing a 3-selenofuran compound promoted by visible light. According to the invention, high propargyl alcohol and diselenide are used as reaction raw materials, and under the condition of room temperature, cyclization/selenization series reaction is carried out by irradiation of visible light to obtain the 3-selenofuran compound. The invention realizes the preparation of the 3-selenofuran compound from the homopropargyl alcohol derivative in the presence of no light catalyst for the first time; the invention does not need to use transition metal and chemical oxidant, and has the advantages of green environmental protection and the like; the invention also has the advantages of mild reaction condition, low cost, little environmental pollution, high yield, good compatibility of functional groups and the like, and has good application potential and research value.

Description

一种可见光促进3-硒基呋喃类化合物的合成方法A visible light-promoted synthesis method of 3-selenofuran compounds

技术领域Technical field

本发明涉及有机合成化学技术领域,具体为一种可见光促进3-硒基呋喃类化合物的合成方法。The invention relates to the technical field of organic synthetic chemistry, specifically a visible light-promoted synthesis method of 3-selenofuran compounds.

背景技术Background technique

呋喃是一类重要的有机芳杂环化合物,其结构存在于很多天然产物、药物和生物活性分子中,呈现出各种不同的生理活性((a)Org.Chem.Front.,2021,8,2608-2642.;(b)Int.J.Rev.Life Sci.,2012,2,7-16;(b)J.Food Biochem.,2018,42,e12597)。呋喃也是有重要价值的有机合成反应砌块以及高分子材料构建的基础骨架((a)ACS Catal.,2021,11,10058-10083;(b)Sustainable Chem.Ser.,2018,2,217-237.)。Furan is an important class of organic aromatic heterocyclic compounds. Its structure exists in many natural products, drugs and biologically active molecules, and exhibits various physiological activities ((a) Org.Chem.Front., 2021, 8, 2608-2642.; (b) Int. J. Rev. Life Sci., 2012, 2, 7-16; (b) J. Food Biochem., 2018, 42, e12597). Furan is also an important building block for organic synthesis reactions and the basic framework for the construction of polymer materials ((a) ACS Catal., 2021, 11, 10058-10083; (b) Sustainable Chem. Ser., 2018, 2, 217-237. ).

硒是人体中一种必须的微量元素。研究表明适量补充硒能起到防止器官老化与病变,延缓衰老,增强免疫,抵御疾病,抵抗有毒害重金属,减轻放化疗副作用,防癌抗癌的作用(Chem.Rev.2004,104,6255-6286)。此外,含硒化合物在有机合成、药物化学和材料科学领域有着广泛的应用。(Eur.J.Org.Chem.,2009,1649-1664)。Selenium is an essential trace element in the human body. Research shows that appropriate supplementation of selenium can prevent organ aging and lesions, delay aging, enhance immunity, resist diseases, resist toxic heavy metals, reduce the side effects of radiotherapy and chemotherapy, and prevent and fight cancer (Chem.Rev.2004,104,6255- 6286). In addition, selenium-containing compounds have extensive applications in the fields of organic synthesis, medicinal chemistry, and materials science. (Eur. J. Org. Chem., 2009, 1649-1664).

鉴于呋喃骨架和硒基独特的生物活性和理化性质,开发新型高效的合成策略构建含硒呋喃一直是合成化学家追求的目标。传统的合成方法通常在适宜硒化试剂存在下,使用过度金属和氧化剂,使预先制备的呋喃环上发生硒化得到目标化合物((a)AsianJ.Org.Chem.,2021,10,2975-2981;(b)Adv.Synth.Catal.,2021,363,3577-3584;(c)ChemistrySelect,2017,2,9227-9232;(d),Asian J.Org.Chem.,2015,4,875-878.)。此外,基于环化-硒化的串联反应策略也是构建含硒呋喃的有效手段。因为该方法可以同时构建呋喃骨架和形成C-Se键。例如,Gilson Zeni等人公开了一种苯基溴化硒诱导的2-炔基苯甲醚化合物环化/硒化反应合成3-硒基苯并呋喃化合物(J.Org.Chem.,2009,74,2153-2162.)。Benhur Godoi等人描述了在二硒醚存在下,CuI催化的2-炔基苯酚发生环化/硒化反应得到3-硒基苯并呋喃(Eur.J.Org.Chem.,2017,2017,6382-6389)。Luling Wu等人公开了一种共轭加成/环化/硒化的多米诺反应合成3-硒基呋喃化合物(Org.Biomol.Chem.,2012,10,3705-3714.)。最近,Suman De Sarkar等人公开了一种由高丙炔醇合成3-硒基呋喃的电化学方法(J.Org.Chem.,2021,86,16084-16094)。In view of the unique biological activities and physicochemical properties of the furan skeleton and selenium group, the development of new and efficient synthetic strategies to construct selenium-containing furans has always been the goal pursued by synthetic chemists. Traditional synthesis methods usually use transition metals and oxidants in the presence of appropriate selenization reagents to selenize the previously prepared furan ring to obtain the target compound ((a) Asian J. Org. Chem., 2021, 10, 2975-2981 ;(b)Adv.Synth.Catal.,2021,363,3577-3584;(c)ChemistrySelect,2017,2,9227-9232;(d),Asian J.Org.Chem.,2015,4,875-878. ). In addition, the tandem reaction strategy based on cyclization-selenation is also an effective means to construct selenium-containing furans. Because this method can simultaneously construct the furan skeleton and form C-Se bonds. For example, Gilson Zeni et al. disclosed a phenylselenium bromide-induced cyclization/selenation reaction of 2-alkynyl anisole compounds to synthesize 3-selenobenzofuran compounds (J.Org.Chem., 2009, 74,2153-2162.). Benhur Godoi et al. described the CuI-catalyzed cyclization/selenation reaction of 2-alkynylphenol in the presence of diselenide to obtain 3-selenobenzofuran (Eur.J.Org.Chem., 2017, 2017, 6382-6389). Luling Wu et al. disclosed a conjugate addition/cyclization/selenization domino reaction to synthesize 3-selenofuran compounds (Org. Biomol. Chem., 2012, 10, 3705-3714.). Recently, Suman De Sarkar et al. disclosed an electrochemical method for synthesizing 3-selenofuran from homopropynyl alcohol (J. Org. Chem., 2021, 86, 16084-16094).

如上所述,现有技术中公开了多种制备3-硒基呋喃的方法,但这些方法均存在一定的缺陷,例如需要昂贵的过渡金属和电化学反应装置、使用化学氧化剂和空气敏感的硒化试剂(ArSeX)以及反应条件苛刻等。As mentioned above, a variety of methods for preparing 3-selenofurans have been disclosed in the prior art, but these methods all have certain shortcomings, such as requiring expensive transition metals and electrochemical reaction devices, using chemical oxidants, and air-sensitive selenium. chemical reagent (ArSeX) and harsh reaction conditions.

可见光是一种清洁无污染的能源,近年来可见光促进的有机合成反应得到了极大的发展(M.-Y.Cao,X.Ren and Z.Lu,Tetrahedron Lett.,2015,56,3732)。然而文献调研表明,基于可见光参与的高炔丙基醇和二硒醚发生串联/硒化反应合成3-硒基呋喃方法至今未曾报道。基于上述原因,探索高效、环保、反应条件温和、官能团兼容性好以及成本低廉的合成3-硒基呋喃化合物的新方法仍具有重要的意义。这也正是本申请得以完成的基础和动力所在。Visible light is a clean and pollution-free energy source. In recent years, organic synthesis reactions promoted by visible light have been greatly developed (M.-Y.Cao, X.Ren and Z.Lu, Tetrahedron Lett., 2015, 56, 3732) . However, literature research shows that the method for the synthesis of 3-selenofuran based on the tandem/selenation reaction of homopropargyl alcohol and diselenide with the participation of visible light has not been reported so far. Based on the above reasons, it is still of great significance to explore new methods for the synthesis of 3-selenofuran compounds that are efficient, environmentally friendly, have mild reaction conditions, have good functional group compatibility, and are low-cost. This is also the basis and motivation for the completion of this application.

发明内容Contents of the invention

本发明的目的在于提供一种可见光促进3-硒基呋喃类化合物的合成方法,以解决上述背景技术中提出的问题。The object of the present invention is to provide a visible light-promoted synthesis method of 3-selenofuran compounds to solve the problems raised in the above background technology.

为实现上述目的,本发明提供如下技术方案:一种可见光促进3-硒基呋喃类化合物的合成方法,包括以下步骤:In order to achieve the above object, the present invention provides the following technical solution: a visible light-promoted synthesis method of 3-selenofuran compounds, including the following steps:

在有机溶剂中,以具有如式(I)所示结构的高炔丙醇衍生物,式(Ⅱ)所示结构的二硒醚为反应原料,在敞口和室温条件下,可见光照射下进行反应,反应结束后,将反应液减压除去溶剂得到粗产品,粗产品经过柱层析纯化得到式(Ⅲ)所示结构的3-硒基呋喃类化合物,反应方程式如下式所示:In an organic solvent, a high propargyl alcohol derivative with a structure shown in formula (I) and a diselenide with a structure shown in formula (II) are used as reaction raw materials, and the reaction is carried out in the open, at room temperature, and under visible light irradiation. reaction. After the reaction, the solvent is removed from the reaction solution under reduced pressure to obtain a crude product. The crude product is purified by column chromatography to obtain a 3-selenofuran compound with a structure shown in formula (III). The reaction equation is as follows:

其中,式(I)化合物为高炔丙醇衍生物,R1和R2各自独立地选自氢原子、C1~C10的直链或支链的烷基、C1~C6烷氧基、卤素、氰基、硝基、三氟甲基、三氟甲氧基、甲酰基。Wherein, the compound of formula (I) is a homopropargyl alcohol derivative, and R1 and R2 are each independently selected from a hydrogen atom, a C1-C10 linear or branched alkyl group, a C1-C6 alkoxy group, a halogen, and a cyano group. , nitro, trifluoromethyl, trifluoromethoxy, formyl.

式(Ⅱ)化合物为二芳基二硒醚或二烷基二硒醚,R3可以选自C1-C10直链或支链的烷基、苄基、一个或多个取代基取代的苯基,所述取代基选自C1~C10烷基、C1~C6烷氧基、卤素、氰基、硝基、三氟甲基、三氟甲氧基、羧基、羟基。The compound of formula (II) is a diaryl diselenide or a dialkyl diselenide, and R3 can be selected from a C1-C10 linear or branched alkyl group, a benzyl group, or a phenyl group substituted by one or more substituents, The substituent is selected from C1 to C10 alkyl, C1 to C6 alkoxy, halogen, cyano, nitro, trifluoromethyl, trifluoromethoxy, carboxyl, and hydroxyl.

优选的,式(I)所示结构的2-炔基苯胺与式(II)所示结构的二硒醚的摩尔比为1∶0.5-1∶1,优选为1∶0.5。Preferably, the molar ratio of 2-alkynylaniline with the structure represented by formula (I) and diselenide with the structure represented by formula (II) is 1:0.5-1:1, preferably 1:0.5.

优选的,所述有机溶剂为二甲基亚砜、N,N-二甲基甲酰胺、乙酸乙酯、正己烷、四氢呋喃、1,4-二氧六烷、氯仿、1,2-二氯乙烷、四氯化碳、甲苯中的至少一种,优选N,N-二甲基甲酰胺(DMF)。Preferably, the organic solvent is dimethyl sulfoxide, N,N-dimethylformamide, ethyl acetate, n-hexane, tetrahydrofuran, 1,4-dioxane, chloroform, 1,2-dichloro At least one of ethane, carbon tetrachloride and toluene, preferably N,N-dimethylformamide (DMF).

优选的,所述可见光为荧光灯、钨灯,LED灯中的任意一种。Preferably, the visible light is any one of fluorescent lamps, tungsten lamps, and LED lamps.

优选的,反应的时间为30h-50h。Preferably, the reaction time is 30h-50h.

优选的,反应结束后,将反应液减压浓缩,将浓缩物通过柱色谱分离,以石油醚和乙酸乙酯体混合液为洗脱剂,其中石油醚:乙酸乙酯的体积比为(30~300):1,收集洗脱液,旋蒸溶剂后得到式(Ⅲ)所示的3-硒基呋喃。Preferably, after the reaction is completed, the reaction solution is concentrated under reduced pressure, and the concentrate is separated by column chromatography, using a mixture of petroleum ether and ethyl acetate as the eluent, wherein the volume ratio of petroleum ether:ethyl acetate is (30 ~300): 1. Collect the eluent and rotary evaporate the solvent to obtain 3-selenofuran represented by formula (III).

与现有技术相比,本发明至少具有以下优点:Compared with the prior art, the present invention at least has the following advantages:

(1)本发明可在空气条件下进行,操作简单。(1) The present invention can be carried out under air conditions and is simple to operate.

(2)本发明使用可见光作为能量来源,以空气中的氧气作为氧化剂,符合绿色化学要求。(2) The present invention uses visible light as the energy source and oxygen in the air as the oxidant, which meets the requirements of green chemistry.

(3)本发明不使用过渡金属催化剂和化学氧化剂,反应选择性高,产物易分离提纯,收率高。(3) The present invention does not use transition metal catalysts and chemical oxidants, has high reaction selectivity, easy separation and purification of the product, and high yield.

(4)本发明只需0.5当量的二硒醚,原子经济性好。(4) The present invention only requires 0.5 equivalents of diselenide and has good atom economy.

具体实施方式Detailed ways

下面将结合本发明实施例中的附图,对本发明实施例中的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings in the embodiments of the present invention. Obviously, the described embodiments are only some of the embodiments of the present invention, rather than all the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those of ordinary skill in the art without creative efforts fall within the scope of protection of the present invention.

本发明提供如下技术方案:一种可见光促进3-硒基呋喃类化合物的合成方法,包括以下步骤:The present invention provides the following technical solution: a visible light-promoted synthesis method of 3-selenofuran compounds, including the following steps:

在有机溶剂中,以具有如式(I)所示结构的2-炔基苯胺,式(Ⅱ)所示结构的二硒醚为反应原料,在敞口和室温条件下,可见光照射下进行反应,反应结束后,将反应液减压除去溶剂得到粗产品,粗产品经过柱层析纯化得到式(Ⅲ)所示结构的3-硒基呋喃类化合物,反应方程式如下式所示:In an organic solvent, 2-alkynylaniline with the structure shown in formula (I) and diselenide with the structure shown in formula (II) are used as reaction raw materials, and the reaction is carried out in the open and at room temperature under visible light irradiation. , after the reaction is completed, the solvent is removed from the reaction solution under reduced pressure to obtain a crude product. The crude product is purified by column chromatography to obtain a 3-selenofuran compound with a structure shown in formula (III). The reaction equation is as follows:

其中,式(I)化合物为高炔丙醇衍生物,R1和R2各自独立地选自氢原子、C1~C10的直链或支链的烷基、C1~C6烷氧基、卤素、氰基、硝基、三氟甲基、三氟甲氧基、甲酰基。Wherein, the compound of formula (I) is a homopropargyl alcohol derivative, and R1 and R2 are each independently selected from a hydrogen atom, a C1-C10 linear or branched alkyl group, a C1-C6 alkoxy group, a halogen, and a cyano group. , nitro, trifluoromethyl, trifluoromethoxy, formyl.

式(Ⅱ)化合物为二芳基二硒醚或二烷基二硒醚,R3可以选自C1-C10直链或支链的烷基、苄基、一个或多个取代基取代的苯基,所述取代基选自C1~C10烷基、C1~C6烷氧基、卤素、氰基、硝基、三氟甲基、三氟甲氧基、羧基、羟基。The compound of formula (II) is a diaryl diselenide or a dialkyl diselenide, and R3 can be selected from a C1-C10 linear or branched alkyl group, a benzyl group, or a phenyl group substituted by one or more substituents, The substituent is selected from C1 to C10 alkyl, C1 to C6 alkoxy, halogen, cyano, nitro, trifluoromethyl, trifluoromethoxy, carboxyl, and hydroxyl.

实施例1Example 1

反应方程式如下式所示:The reaction equation is as follows:

敞口条件下,向装有磁力搅拌子的10毫升反应管中装入1,4-二苯基-3-丁炔-1-醇(0.2毫摩尔),二苯基二硒醚(0.1毫摩尔),DMF(1毫升),加毕,将23瓦白色紧凑型荧光灯放在距离反应管1厘米的地方,敞口条件下室温反应40小时,反应完成后,将有机相通过旋转蒸发器除去溶剂,残余物用硅胶柱进行纯化(硅胶规格为200目~300目,洗脱剂为石油醚/乙酸乙酯=100/1),得到目标化合物64毫克,产率为85%。Under open conditions, add 1,4-diphenyl-3-butyn-1-ol (0.2 mmol) and diphenyl diselenide (0.1 mmol) into a 10 ml reaction tube equipped with a magnetic stirrer. mol), DMF (1 ml), after addition, place a 23-watt white compact fluorescent lamp 1 cm away from the reaction tube, and react at room temperature for 40 hours under open conditions. After the reaction is completed, remove the organic phase through a rotary evaporator. Solvent, and the residue was purified using a silica gel column (silica gel specifications were 200 mesh to 300 mesh, and the eluent was petroleum ether/ethyl acetate = 100/1) to obtain 64 mg of the target compound with a yield of 85%.

所得产物核磁图谱数据为:1H NMR(400MHz,CDCl3):δ8.15(d,J=7.9Hz,2H),7.78(d,J=7.9Hz,2H),7.51(dd,J=14.1,6.8Hz,6H),7.42-7.23(m,5H),6.81(s,1H).13C NMR(100MHz,CDCl3):δ153.5,153.3,131.9,130.6,130.4,129.9,129.1,128.8,128.7,128.2,126.5,126.4,124.1,114.5,106.1.The NMR spectrum data of the obtained product are: 1 H NMR (400MHz, CDCl 3 ): δ8.15 (d, J = 7.9 Hz, 2H), 7.78 (d, J = 7.9 Hz, 2H), 7.51 (dd, J = 14.1 ,6.8Hz,6H),7.42-7.23(m,5H),6.81(s,1H). 13 C NMR (100MHz, CDCl 3 ): δ153.5,153.3,131.9,130.6,130.4,129.9,129.1,128.8,128.7 ,128.2,126.5,126.4,124.1,114.5,106.1.

实施例2Example 2

反应方程式如下式所示:The reaction equation is as follows:

敞口条件下,向装有磁力搅拌子的10毫升反应管中装入1-苯基-4-(4’-甲基苯基)-3-丁炔-1-醇(0.2毫摩尔),二苯基二硒醚(0.1毫摩尔),DMF(1毫升),加毕,将23瓦白色紧凑型荧光灯放在距离反应管1厘米的地方,敞口条件下室温反应40小时,反应完成后,将有机相通过旋转蒸发器除去溶剂,残余物用硅胶柱进行纯化(硅胶规格为200目~300目,洗脱剂为石油醚/乙酸乙酯=90/1),得到目标化合物65毫克,产率为83%。Under open conditions, add 1-phenyl-4-(4'-methylphenyl)-3-butyn-1-ol (0.2 mmol) into a 10 ml reaction tube equipped with a magnetic stirrer. After adding diphenyl diselenide (0.1 mmol) and DMF (1 ml), place a 23-watt white compact fluorescent lamp 1 cm away from the reaction tube and react at room temperature for 40 hours under open conditions. After the reaction is completed , remove the solvent from the organic phase through a rotary evaporator, and purify the residue with a silica gel column (silica gel specifications are 200 mesh to 300 mesh, and the eluent is petroleum ether/ethyl acetate = 90/1) to obtain 65 mg of the target compound. The yield was 83%.

所得产物核磁图谱数据为:1H NMR(400MHz,CDCl3):δ7.90(d,J=7.9Hz,2H),7.68(d,J=7.9Hz,2H),7.38(t,J=7.6Hz,4H),7.27(t,J=7.4Hz,1H),7.30-7.19(m,5H),6.71(s,1H),2.39(s,3H).13C NMR(100MHz,CDCl3):δ153.3,152.6,137.8,131.6,129.6,129.0,128.8,128.3,127.4,127.3,126.2,125.9,123.8,113.7,104.6,21.1.The NMR spectrum data of the obtained product are: 1 H NMR (400MHz, CDCl 3 ): δ7.90 (d, J = 7.9 Hz, 2H), 7.68 (d, J = 7.9 Hz, 2H), 7.38 (t, J = 7.6 Hz, 4H), 7.27 (t, J = 7.4Hz, 1H), 7.30-7.19 (m, 5H), 6.71 (s, 1H), 2.39 (s, 3H). 13 C NMR (100MHz, CDCl 3 ): δ153.3,152.6,137.8,131.6,129.6,129.0,128.8,128.3,127.4,127.3,126.2,125.9,123.8,113.7,104.6,21.1.

实施例3Example 3

反应方程式如下式所示:The reaction equation is as follows:

敞口条件下,向装有磁力搅拌子的10毫升反应管中装入1-苯基-4-(4’-甲氧基苯基)-3-丁炔-1-醇(0.2毫摩尔),二苯基二硒醚(0.1毫摩尔),DMF(1毫升),加毕,将23瓦白色紧凑型荧光灯放在距离反应管1厘米的地方,敞口条件下室温反应40小时,反应完成后,将有机相通过旋转蒸发器除去溶剂,残余物用硅胶柱进行纯化(硅胶规格为200目~300目,洗脱剂为石油醚/乙酸乙酯=70/1),得到目标化合物65毫克,产率为80%。Under open conditions, add 1-phenyl-4-(4'-methoxyphenyl)-3-butyn-1-ol (0.2 mmol) into a 10 ml reaction tube equipped with a magnetic stirrer. , diphenyl diselenide (0.1 mmol), DMF (1 ml), after addition, place a 23-watt white compact fluorescent lamp 1 cm away from the reaction tube, and react at room temperature for 40 hours under open conditions. The reaction is completed. Afterwards, the solvent was removed from the organic phase through a rotary evaporator, and the residue was purified using a silica gel column (silica gel specifications were 200 mesh to 300 mesh, and the eluent was petroleum ether/ethyl acetate = 70/1) to obtain 65 mg of the target compound. , the yield is 80%.

所得产物核磁图谱数据为:1H NMR(400MHz,CDCl3):δ8.01(d,J=8.7Hz,2H),7.82-7.60(m,2H),7.50-7.26(m,4H),6.99(d,J=8.8Hz,2H),6.79(s,1H),3.88(s,3H).13C NMR(100MHz,CDCl3):δ159.2,153.9,152.5,132.0,130.1,129.5,129.1,128.8,127.9,127.3,126.0,123.5,123.1,113.9,113.8,103.5,55.1.The NMR spectrum data of the obtained product are: 1 H NMR (400MHz, CDCl 3 ): δ8.01 (d, J = 8.7Hz, 2H), 7.82-7.60 (m, 2H), 7.50-7.26 (m, 4H), 6.99 (d, J=8.8Hz, 2H), 6.79 (s, 1H), 3.88 (s, 3H). 13 C NMR (100MHz, CDCl 3 ): δ159.2, 153.9, 152.5, 132.0, 130.1, 129.5, 129.1, 128.8 ,127.9,127.3,126.0,123.5,123.1,113.9,113.8,103.5,55.1.

实施例4Example 4

反应方程式如下式所示:The reaction equation is as follows:

敞口条件下,向装有磁力搅拌子的10毫升反应管中装入1-苯基-4-(4’-氯苯基)-3-丁炔-1-醇(0.2毫摩尔),二苯基二硒醚(0.1毫摩尔),DMF(1毫升),加毕,将23瓦白色紧凑型荧光灯放在距离反应管1厘米的地方,敞口条件下室温反应40小时,反应完成后,将有机相通过旋转蒸发器除去溶剂,残余物用硅胶柱进行纯化(硅胶规格为200目~300目,洗脱剂为石油醚/乙酸乙酯=100/1),得到目标化合物73毫克,产率为89%。Under open conditions, put 1-phenyl-4-(4'-chlorophenyl)-3-butyn-1-ol (0.2 mmol) into a 10 ml reaction tube equipped with a magnetic stirrer. After adding phenyl diselenide (0.1 mmol) and DMF (1 ml), place a 23-watt white compact fluorescent lamp 1 cm away from the reaction tube and react at room temperature for 40 hours under open conditions. After the reaction is completed, The solvent was removed from the organic phase through a rotary evaporator, and the residue was purified using a silica gel column (silica gel specifications were 200 mesh to 300 mesh, and the eluent was petroleum ether/ethyl acetate = 100/1) to obtain 73 mg of the target compound. The rate is 89%.

所得产物核磁图谱数据为:1H NMR(400MHz,CDCl3):δ7.88(d,J=8.3Hz,2H),7.55(d,J=8.0Hz,2H),7.33-7.24(m,5H),7.22-7.08(m,5H),6.62(s,1H).13C NMR(100MHz,CDCl3):δ153.9,152.6,134.2,132.1,131.9,130.6,130.3,130.1,129.3,129.0,128.4,127.5,127.3,124.9,114.8,107.1.The obtained product NMR spectrum data are: 1 H NMR (400MHz, CDCl 3 ): δ7.88 (d, J = 8.3 Hz, 2H), 7.55 (d, J = 8.0 Hz, 2H), 7.33-7.24 (m, 5H) ),7.22-7.08(m,5H),6.62(s,1H). 13 C NMR (100MHz, CDCl 3 ): δ153.9,152.6,134.2,132.1,131.9,130.6,130.3,130.1,129.3,129.0,128.4, 127.5,127.3,124.9,114.8,107.1.

实施例5Example 5

反应方程式如下式所示:The reaction equation is as follows:

敞口条件下,向装有磁力搅拌子的10毫升反应管中装入1-苯基-4-(4’-甲酯基苯基)-3-丁炔-1-醇(0.2毫摩尔),二苯基二硒醚(0.1毫摩尔),DMF(1毫升),加毕,将23瓦白色紧凑型荧光灯放在距离反应管1厘米的地方,敞口条件下室温反应40小时,反应完成后,将有机相通过旋转蒸发器除去溶剂,残余物用硅胶柱进行纯化(硅胶规格为200目~300目,洗脱剂为石油醚/乙酸乙酯=60/1),得到目标化合物78毫克,产率为90%。Under open conditions, add 1-phenyl-4-(4'-methoxyphenyl)-3-butyn-1-ol (0.2 mmol) into a 10 ml reaction tube equipped with a magnetic stirrer. , diphenyl diselenide (0.1 mmol), DMF (1 ml), after addition, place a 23-watt white compact fluorescent lamp 1 cm away from the reaction tube, and react at room temperature for 40 hours under open conditions. The reaction is completed. Afterwards, the solvent was removed from the organic phase through a rotary evaporator, and the residue was purified using a silica gel column (silica gel specifications were 200 mesh to 300 mesh, and the eluent was petroleum ether/ethyl acetate = 60/1) to obtain 78 mg of the target compound. , the yield is 90%.

所得产物核磁图谱数据为:1H NMR(400MHz,CDCl3):δ8.14-8.00(m,4H),7.79-7.72(m,2H),7.50-7.26(m,8H),6.75(s,1H),3.93(s,3H).13C NMR(100MHz,CDCl3):δ166.0,153.1,151.0,133.9,130.1,128.8,128.7,128.6,128.0,127.4,126.5,124.9,124.8,123.5,113.3,108.3,51.6.The NMR spectrum data of the obtained product are: 1 H NMR (400MHz, CDCl 3 ): δ8.14-8.00(m,4H),7.79-7.72(m,2H),7.50-7.26(m,8H),6.75(s, 1H), 3.93 (s, 3H). 13 C NMR (100MHz, CDCl 3 ): δ166.0,153.1,151.0,133.9,130.1,128.8,128.7,128.6,128.0,127.4,126.5,124.9,124.8,123.5,113.3 , 108.3,51.6.

实施例6Example 6

反应方程式如下式所示:The reaction equation is as follows:

敞口条件下,向装有磁力搅拌子的10毫升反应管中装入1-苯基-4-(4’-氰基苯基)-3-丁炔-1-醇(0.2毫摩尔),二苯基二硒醚(0.1毫摩尔),DMF(1毫升),加毕,将23瓦白色紧凑型荧光灯放在距离反应管1厘米的地方,敞口条件下室温反应40小时,反应完成后,将有机相通过旋转蒸发器除去溶剂,残余物用硅胶柱进行纯化(硅胶规格为200目~300目,洗脱剂为石油醚/乙酸乙酯=70/1),得到目标化合物72毫克,产率为90%。Under open conditions, add 1-phenyl-4-(4'-cyanophenyl)-3-butyn-1-ol (0.2 mmol) into a 10 ml reaction tube equipped with a magnetic stirrer. After adding diphenyl diselenide (0.1 mmol) and DMF (1 ml), place a 23-watt white compact fluorescent lamp 1 cm away from the reaction tube and react at room temperature for 40 hours under open conditions. After the reaction is completed , remove the solvent from the organic phase through a rotary evaporator, and purify the residue with a silica gel column (silica gel specifications are 200 mesh to 300 mesh, and the eluent is petroleum ether/ethyl acetate = 70/1) to obtain 72 mg of the target compound. The yield is 90%.

所得产物核磁图谱数据为:1H NMR(400MHz,CDCl3):δ8.18(d,J=8.2Hz,2H),7.69(dd,J=13.0,8.2Hz,4H),7.40(t,J=7.7Hz,4H),7.36(t,J=7.6Hz,1H),7.35(d,J=5.2Hz,3H),6.69(s,1H).13C NMR(100MHz,CDCl3):δ155.5,151.3,135.9,133.3,132.8,131.9,130.7,130.4,130.0,129.8,128.8,127.3,125.4,120.0,115.6,111.7,111.4.The NMR spectrum data of the obtained product are: 1 H NMR (400MHz, CDCl 3 ): δ8.18 (d, J = 8.2 Hz, 2H), 7.69 (dd, J = 13.0, 8.2 Hz, 4H), 7.40 (t, J =7.7Hz, 4H), 7.36 (t, J = 7.6Hz, 1H), 7.35 (d, J = 5.2Hz, 3H), 6.69 (s, 1H). 13 C NMR (100MHz, CDCl 3 ): δ155. 5,151.3,135.9,133.3,132.8,131.9,130.7,130.4,130.0,129.8,128.8,127.3,125.4,120.0,115.6,111.7,111.4.

实施例7Example 7

反应方程式如下式所示:The reaction equation is as follows:

敞口条件下,向装有磁力搅拌子的10毫升反应管中装入1-(4’-氯苯基)-4-苯基-3-丁炔-1-醇(0.2毫摩尔),二苯基二硒醚(0.1毫摩尔),DMF(1毫升),加毕,将23瓦白色紧凑型荧光灯放在距离反应管1厘米的地方,敞口条件下室温反应40小时,反应完成后,将有机相通过旋转蒸发器除去溶剂,残余物用硅胶柱进行纯化(硅胶规格为200目~300目,洗脱剂为石油醚/乙酸乙酯=90/1),得到目标化合物71毫克,产率为87%。Under open conditions, put 1-(4'-chlorophenyl)-4-phenyl-3-butyn-1-ol (0.2 mmol) into a 10 ml reaction tube equipped with a magnetic stirrer. After adding phenyl diselenide (0.1 mmol) and DMF (1 ml), place a 23-watt white compact fluorescent lamp 1 cm away from the reaction tube and react at room temperature for 40 hours under open conditions. After the reaction is completed, The solvent was removed from the organic phase through a rotary evaporator, and the residue was purified using a silica gel column (silica gel specifications were 200 mesh to 300 mesh, and the eluent was petroleum ether/ethyl acetate = 90/1) to obtain 71 mg of the target compound. The rate is 87%.

所得产物核磁图谱数据为:1H NMR(400MHz,CDCl3):δ8.06(d,J=7.9Hz,2H),7.65(d,J=8.5Hz,2H),7.45(dd,J=9.9,5.4Hz,4H),7.39(d,J=8.5Hz,2H),7.36-7.22(m,4H),6.75(s,1H).13C NMR(100MHz,CDCl3):δ154.5,152.9,134.5,132.6,132.0,131.3,130.3,130.0,129.5,129.1,129.0,128.2,127.5,126.1,115.1,107.1.The NMR spectrum data of the obtained product are: 1 H NMR (400MHz, CDCl 3 ): δ8.06 (d, J = 7.9 Hz, 2H), 7.65 (d, J = 8.5 Hz, 2H), 7.45 (dd, J = 9.9 ,5.4Hz,4H),7.39(d,J=8.5Hz,2H),7.36-7.22(m,4H),6.75(s,1H). 13 C NMR (100MHz, CDCl 3 ): δ154.5,152.9,134.5 ,132.6,132.0,131.3,130.3,130.0,129.5,129.1,129.0,128.2,127.5,126.1,115.1,107.1.

实施例8Example 8

反应方程式如下式所示:The reaction equation is as follows:

敞口条件下,向装有磁力搅拌子的10毫升反应管中装入1-(4’-溴苯基)-4-苯基-3-丁炔-1-醇(0.2毫摩尔),二苯基二硒醚(0.1毫摩尔),DMF(1毫升),加毕,将23瓦白色紧凑型荧光灯放在距离反应管1厘米的地方,敞口条件下室温反应40小时,反应完成后,将有机相通过旋转蒸发器除去溶剂,残余物用硅胶柱进行纯化(硅胶规格为200目~300目,洗脱剂为石油醚/乙酸乙酯=90/1),得到目标化合物74毫克,产率为82%。Under open conditions, put 1-(4'-bromophenyl)-4-phenyl-3-butyn-1-ol (0.2 mmol) into a 10 ml reaction tube equipped with a magnetic stirrer. After adding phenyl diselenide (0.1 mmol) and DMF (1 ml), place a 23-watt white compact fluorescent lamp 1 cm away from the reaction tube and react at room temperature for 40 hours under open conditions. After the reaction is completed, The solvent was removed from the organic phase through a rotary evaporator, and the residue was purified using a silica gel column (silica gel specifications were 200 mesh to 300 mesh, and the eluent was petroleum ether/ethyl acetate = 90/1) to obtain 74 mg of the target compound. The rate is 82%.

所得产物核磁图谱数据为:1H NMR(400MHz,CDCl3):δ8.00(d,J=7.9Hz,2H),7.53(d,J=8.2Hz,2H),7.49(d,J=8.4Hz,2H),7.40-7.17(m,8H),6.69(s,1H).13C NMR(100MHz,CDCl3):δ153.0,151.7,131.9,131.73,130.1,129.1,128.2,128.1,128.0,127.3,126.6,125.9,125.0,121.7,113.8,105.8.The NMR spectrum data of the obtained product are: 1 H NMR (400MHz, CDCl 3 ): δ8.00 (d, J = 7.9 Hz, 2H), 7.53 (d, J = 8.2 Hz, 2H), 7.49 (d, J = 8.4 Hz, 2H), 7.40-7.17 (m, 8H), 6.69 (s, 1H). 13 C NMR (100MHz, CDCl 3 ): δ153.0,151.7,131.9,131.73,130.1,129.1,128.2,128.1,128.0,127.3 ,126.6,125.9,125.0,121.7,113.8,105.8.

实施例9Example 9

反应方程式如下式所示:The reaction equation is as follows:

敞口条件下,向装有磁力搅拌子的10毫升反应管中装入1,4-二苯基-3-丁炔-1-醇(0.2毫摩尔),二(4-甲基苯基)二硒醚(0.1毫摩尔),DMF(1毫升),加毕,将23瓦白色紧凑型荧光灯放在距离反应管1厘米的地方,敞口条件下室温反应40小时,反应完成后,将有机相通过旋转蒸发器除去溶剂,残余物用硅胶柱进行纯化(硅胶规格为200目~300目,洗脱剂为石油醚/乙酸乙酯=90/1),得到目标化合物68毫克,产率为88%。Under open conditions, add 1,4-diphenyl-3-butyn-1-ol (0.2 mmol) and bis(4-methylphenyl) into a 10 ml reaction tube equipped with a magnetic stirrer. After adding diselenide (0.1 mmol) and DMF (1 ml), place a 23-watt white compact fluorescent lamp 1 cm away from the reaction tube and react at room temperature for 40 hours under open conditions. After the reaction is completed, the organic The solvent was removed from the phase by a rotary evaporator, and the residue was purified with a silica gel column (silica gel specifications were 200 mesh to 300 mesh, and the eluent was petroleum ether/ethyl acetate = 90/1) to obtain 68 mg of the target compound, with a yield of 88%.

所得产物核磁图谱数据为:7.87-7.60(m,5H),7.51-7.40(m,4H),7.28(d J=7.9Hz,2H),7.21-7.16(m,3H),6.69(s,1),2.32(s,3H).13C NMR(100MHz,CDCl3):δ152.1,149.6,135.7,136.2,133.8,133.0,132.9,130.7,130.1,129.0,128.9,128.8,127.3,125.1,114.7,106.3,21.6.The NMR spectrum data of the obtained product are: 7.87-7.60(m,5H),7.51-7.40(m,4H),7.28(d J=7.9Hz,2H),7.21-7.16(m,3H),6.69(s,1 ), 2.32 (s, 3H). 13 C NMR (100MHz, CDCl 3 ): δ152.1,149.6,135.7,136.2,133.8,133.0,132.9,130.7,130.1,129.0,128.9,128.8,127.3,125.1,114.7,10 6.3 ,21.6.

实施例10Example 10

反应方程式如下式所示:The reaction equation is as follows:

敞口条件下,向装有磁力搅拌子的10毫升反应管中装入1,4-二苯基-3-丁炔-1-醇(0.2毫摩尔),二(4-甲氧基苯基)二硒醚(0.1毫摩尔),DMF(1毫升),加毕,将23瓦白色紧凑型荧光灯放在距离反应管1厘米的地方,敞口条件下室温反应40小时,反应完成后,将有机相通过旋转蒸发器除去溶剂,残余物用硅胶柱进行纯化(硅胶规格为200目~300目,洗脱剂为石油醚/乙酸乙酯=90/1),得到目标化合物66毫克,产率为82%。Under open conditions, add 1,4-diphenyl-3-butyn-1-ol (0.2 mmol) and bis(4-methoxyphenyl) into a 10 ml reaction tube equipped with a magnetic stirrer. ) diselenide (0.1 mmol), DMF (1 ml), after addition, place a 23-watt white compact fluorescent lamp 1 cm away from the reaction tube, and react at room temperature for 40 hours under open conditions. After the reaction is completed, The solvent was removed from the organic phase using a rotary evaporator, and the residue was purified using a silica gel column (silica gel specifications were 200 mesh to 300 mesh, and the eluent was petroleum ether/ethyl acetate = 90/1) to obtain 66 mg of the target compound, yield is 82%.

所得产物核磁图谱数据为:1H NMR(400MHz,CDCl3):δ8.09(d,J=8.0Hz,2H),7.74(d,J=7.9Hz,2H),7.52-7.40(m,6H),7.39-7.25(m,2H),6.88(d,J=8.6Hz,2H),6.65(s,1H),3.82(s,3H).13C NMR(100MHz,CDCl3):δ150.1,153.5,152.3,134.6,131.3,130.9,129.3,128.9,128.5,126.6,124.7,121.6,115.8,113.6,108.7,56.1.The NMR spectrum data of the obtained product are: 1 H NMR (400MHz, CDCl 3 ): δ8.09 (d, J = 8.0 Hz, 2H), 7.74 (d, J = 7.9 Hz, 2H), 7.52-7.40 (m, 6H) ), 7.39-7.25 (m, 2H), 6.88 (d, J = 8.6Hz, 2H), 6.65 (s, 1H), 3.82 (s, 3H). 13 C NMR (100MHz, CDCl 3 ): δ 150.1, 153.5 ,152.3,134.6,131.3,130.9,129.3,128.9,128.5,126.6,124.7,121.6,115.8,113.6,108.7,56.1.

综上所述,本发明制备方法以高炔丙基醇和二硒醚为原料,以二甲基亚砜、N,N-二甲基甲酰胺、乙酸乙酯、正己烷、四氢呋喃、1,4-二氧六烷、氯仿、1,2-二氯乙烷、四氯化碳、甲苯中的至少一种,反应温度为室温,敞口条件下白色荧光灯照射,高效合成出3-硒基呋喃化合物,该方法与传统的合成方法相比,具有反应条件温和,在室温下可顺利进行;操作简单,所有操作均可在敞开体系中进行;同时本方法避免了使用昂贵的过渡金属催化剂、光催化剂和氧化剂,具有经济和绿色环保等特点。To sum up, the preparation method of the present invention uses high propargyl alcohol and diselenide as raw materials, dimethyl sulfoxide, N, N-dimethylformamide, ethyl acetate, n-hexane, tetrahydrofuran, 1,4 - At least one of dioxane, chloroform, 1,2-dichloroethane, carbon tetrachloride, and toluene, the reaction temperature is room temperature, and 3-selenofuran is efficiently synthesized under exposure to white fluorescent light Compounds, compared with traditional synthesis methods, this method has mild reaction conditions and can proceed smoothly at room temperature; the operation is simple, and all operations can be performed in an open system; at the same time, this method avoids the use of expensive transition metal catalysts, light Catalysts and oxidants are economical and environmentally friendly.

尽管已经示出和描述了本发明的实施例,对于本领域的普通技术人员而言,可以理解在不脱离本发明的原理和精神的情况下可以对这些实施例进行多种变化、修改、替换和变型,本发明的范围由所附权利要求及其等同物限定。Although the embodiments of the present invention have been shown and described, those of ordinary skill in the art will understand that various changes, modifications, and substitutions can be made to these embodiments without departing from the principles and spirit of the invention. and modifications, the scope of the invention is defined by the appended claims and their equivalents.

Claims (5)

1.一种可见光促进3-硒基呋喃类化合物的合成方法,其特征在于:包括以下步骤:在有机溶剂中,以具有如式(I)所示结构的高炔丙醇衍生物,式(Ⅱ)所示结构的二硒醚为反应原料,在敞口和室温条件下,可见光照射下进行反应,反应结束后,将反应液减压除去溶剂得到粗产品,粗产品经过柱层析纯化得到式(Ⅲ)所示结构的3-硒基呋喃类化合物,反应方程式如下式所示:1. A visible light-promoted synthesis method of 3-selenofuran compounds, characterized in that: comprising the following steps: in an organic solvent, with a homopropargyl alcohol derivative having a structure shown in formula (I), formula ( The diselenide of the structure shown in Ⅱ) is used as the reaction raw material. The reaction is carried out in the open and at room temperature under visible light irradiation. After the reaction is completed, the solvent is removed from the reaction solution under reduced pressure to obtain a crude product. The crude product is purified by column chromatography. For 3-selenofuran compounds with the structure shown in formula (III), the reaction equation is as follows: 其中,式(I)化合物为高炔丙醇衍生物,R1和R2各自独立地选自氢原子、C1~C10的直链或支链的烷基、C1~C6烷氧基、卤素、氰基、硝基、三氟甲基、三氟甲氧基、甲酰基;Wherein, the compound of formula (I) is a homopropargyl alcohol derivative, and R1 and R2 are each independently selected from a hydrogen atom, a C1-C10 linear or branched alkyl group, a C1-C6 alkoxy group, a halogen, and a cyano group. , nitro, trifluoromethyl, trifluoromethoxy, formyl; 式(Ⅱ)化合物为二芳基二硒醚或二烷基二硒醚,R3选自C1-C10直链或支链的烷基、苄基、一个或多个取代基取代的苯基,所述取代基选自C1~C10烷基、C1~C6烷氧基、卤素、氰基、硝基、三氟甲基、三氟甲氧基、羧基、羟基;The compound of formula (II) is a diaryl diselenide or a dialkyl diselenide, and R3 is selected from C1-C10 linear or branched alkyl, benzyl, and phenyl substituted by one or more substituents, so The substituents are selected from C1 to C10 alkyl, C1 to C6 alkoxy, halogen, cyano, nitro, trifluoromethyl, trifluoromethoxy, carboxyl, and hydroxyl; 所述有机溶剂为N,N-二甲基甲酰胺;所述可见光为荧光灯。The organic solvent is N,N-dimethylformamide; the visible light is fluorescent lamp. 2.根据权利要求1所述的一种可见光促进3-硒基呋喃类化合物的合成方法,其特征在于:式(I)所示结构的2-炔基苯胺与式(Ⅱ)所示结构的二硒醚的摩尔比为1∶0.5-1∶1。2. A kind of visible light-promoted synthesis method of 3-selenofuran compounds according to claim 1, characterized in that: 2-alkynylaniline of the structure shown in formula (I) and 2-alkynylaniline of the structure shown in formula (II) The molar ratio of diselenide is 1:0.5-1:1. 3.根据权利要求2所述的一种可见光促进3-硒基呋喃类化合物的合成方法,其特征在于:式(I)所示结构的2-炔基苯胺与式(Ⅱ)所示结构的二硒醚的摩尔比为1∶0.5。3. A kind of visible light-promoted synthesis method of 3-selenofuran compounds according to claim 2, characterized in that: the 2-alkynylaniline of the structure shown in formula (I) and the structure shown in formula (II) The molar ratio of diselenide is 1:0.5. 4.根据权利要求1所述的一种可见光促进3-硒基呋喃类化合物的合成方法,其特征在于:反应的时间为30h-50h。4. A visible light-promoted synthesis method of 3-selenofuran compounds according to claim 1, characterized in that: the reaction time is 30h-50h. 5.根据权利要求1所述的一种可见光促进3-硒基呋喃类化合物的合成方法,其特征在于:反应结束后,将反应液减压浓缩,将浓缩物通过柱色谱分离,以石油醚和乙酸乙酯体混合液为洗脱剂,其中石油醚:乙酸乙酯的体积比为(30~300):1,收集洗脱液,旋蒸溶剂后得到式(Ⅲ)所示的3-硒基呋喃。5. A kind of visible light-promoted synthesis method of 3-selenofuran compounds according to claim 1, characterized in that: after the reaction is completed, the reaction solution is concentrated under reduced pressure, and the concentrate is separated by column chromatography, and is separated with petroleum ether. The mixture with ethyl acetate is used as the eluent, in which the volume ratio of petroleum ether: ethyl acetate is (30-300): 1. The eluent is collected, and the solvent is rotary evaporated to obtain 3- represented by formula (III). Selenofurans.
CN202210439256.7A 2022-04-25 2022-04-25 Synthesis method of 3-selenofurans compound promoted by visible light Active CN115197180B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202210439256.7A CN115197180B (en) 2022-04-25 2022-04-25 Synthesis method of 3-selenofurans compound promoted by visible light

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202210439256.7A CN115197180B (en) 2022-04-25 2022-04-25 Synthesis method of 3-selenofurans compound promoted by visible light

Publications (2)

Publication Number Publication Date
CN115197180A CN115197180A (en) 2022-10-18
CN115197180B true CN115197180B (en) 2024-01-23

Family

ID=83575065

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202210439256.7A Active CN115197180B (en) 2022-04-25 2022-04-25 Synthesis method of 3-selenofurans compound promoted by visible light

Country Status (1)

Country Link
CN (1) CN115197180B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117142997A (en) * 2023-08-30 2023-12-01 南通大学 A kind of visible light-promoted synthesis method of selenium-based dibenzocycloheptanone
CN117304132B (en) * 2023-09-15 2024-12-06 南通大学 A method for synthesizing selenothiazoline compounds promoted by visible light

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113603653A (en) * 2021-08-23 2021-11-05 南通大学 A kind of visible light-promoted synthesis method of seleno-oxazolidine-2.4-dione

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113603653A (en) * 2021-08-23 2021-11-05 南通大学 A kind of visible light-promoted synthesis method of seleno-oxazolidine-2.4-dione

Also Published As

Publication number Publication date
CN115197180A (en) 2022-10-18

Similar Documents

Publication Publication Date Title
CN115197180B (en) Synthesis method of 3-selenofurans compound promoted by visible light
CN108101734A (en) A kind of method that ruthenium catalysis fluorine-containing aromatic ketone prepares more virtue substitution naphthalene derivativeses with tolans reaction
CN110386885A (en) A kind of visible light promotion β-carbonyl sulphones preparation method
CN105085217B (en) It is a kind of using copper as the synthetic method of catalyst benzfluorenone and its derivative
CN114380675A (en) A kind of method that visible light induces the reaction of halogenated aromatic hydrocarbon and phenol compound to synthesize arylphenol
CN112159312B (en) A kind of synthetic method of triarylmethane compound
CN108569942A (en) A kind of preparation method of α-trifluoromethylthio substituted acetophenone class compound
CN109232525B (en) Photocatalytic oxidation synthesis method of thioxanthone compound
CN107602452B (en) A kind of synthetic method of 3-acyl pyridine compounds
CN116283707A (en) Synthesis method of indole compound promoted by visible light
CN108864173B (en) Process for converting substituted sodium aryl sulfinate to aryl tri-n-butyl tin
CN118908997A (en) Preparation method and application of alpha-phosphonyl imine compound
CN106496091B (en) A kind of 2 dicarbapentaborane substituted azole class compounds and preparation method thereof
CN115322100A (en) Delta, epsilon-alkenyl ketone compound and preparation method and application thereof
CN115215778A (en) Alpha-difluoro seleno methyl ketone derivative and preparation method thereof
CN116120326B (en) A kind of α-methyldeoxy-codonopsis alkaloid compound and its synthesis method
CN110028438B (en) A kind of synthetic method of 3-phenyl-3-indole trifluoromethyl acetone derivatives
CN115028568B (en) Synthesis method of 3-selenoindole compound promoted by visible light
CN105801411B (en) A kind of synthetic method of the aryl methyl ketone derivative of 2 aromatic acid base 1
CN105820096B (en) A kind of method for preparing substitution ethyl aryl sulfone
CN117088826B (en) Synthesis method of polysubstituted oxazole promoted by visible light
CN118852084A (en) A method for synthesizing selenoflavanones by promoting visible light
CN117142997A (en) A kind of visible light-promoted synthesis method of selenium-based dibenzocycloheptanone
CN106977447B (en) A kind of preparation method of the carbazole compound of the hydroxyl of symmetrical configuration
CN114524790A (en) C2 alkynyl disubstituted 2H-chromene compound and preparation method thereof

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant