CN113200899A - 一种芳基硒醚类化合物及其合成方法 - Google Patents
一种芳基硒醚类化合物及其合成方法 Download PDFInfo
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- CN113200899A CN113200899A CN202110544833.4A CN202110544833A CN113200899A CN 113200899 A CN113200899 A CN 113200899A CN 202110544833 A CN202110544833 A CN 202110544833A CN 113200899 A CN113200899 A CN 113200899A
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- selenoxide
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- -1 Aryl selenide compound Chemical class 0.000 title claims abstract description 20
- 238000010189 synthetic method Methods 0.000 title claims abstract description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 46
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 239000003960 organic solvent Substances 0.000 claims abstract description 15
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 150000003440 styrenes Chemical class 0.000 claims abstract description 8
- XIMIGUBYDJDCKI-UHFFFAOYSA-N diselenium Chemical compound [Se]=[Se] XIMIGUBYDJDCKI-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000009835 boiling Methods 0.000 claims abstract description 4
- 238000002156 mixing Methods 0.000 claims abstract description 3
- LKUDPHPHKOZXCD-UHFFFAOYSA-N 1,3,5-trimethoxybenzene Chemical compound COC1=CC(OC)=CC(OC)=C1 LKUDPHPHKOZXCD-UHFFFAOYSA-N 0.000 claims description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- AGIQIOSHSMJYJP-UHFFFAOYSA-N 1,2,4-Trimethoxybenzene Chemical compound COC1=CC=C(OC)C(OC)=C1 AGIQIOSHSMJYJP-UHFFFAOYSA-N 0.000 claims description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 230000002194 synthesizing effect Effects 0.000 claims description 10
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- WGGLDBIZIQMEGH-UHFFFAOYSA-N 1-bromo-4-ethenylbenzene Chemical compound BrC1=CC=C(C=C)C=C1 WGGLDBIZIQMEGH-UHFFFAOYSA-N 0.000 claims description 6
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 claims description 6
- JWVTWJNGILGLAT-UHFFFAOYSA-N 1-ethenyl-4-fluorobenzene Chemical compound FC1=CC=C(C=C)C=C1 JWVTWJNGILGLAT-UHFFFAOYSA-N 0.000 claims description 6
- KCIZTNZGSBSSRM-UHFFFAOYSA-N 3,4,5-Trimethoxytoluene Chemical compound COC1=CC(C)=CC(OC)=C1OC KCIZTNZGSBSSRM-UHFFFAOYSA-N 0.000 claims description 6
- VTCDZPUMZAZMSB-UHFFFAOYSA-N 3,4,5-trimethoxyphenol Chemical compound COC1=CC(O)=CC(OC)=C1OC VTCDZPUMZAZMSB-UHFFFAOYSA-N 0.000 claims description 6
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 6
- YWWZCHLUQSHMCL-UHFFFAOYSA-N diphenyl diselenide Chemical compound C=1C=CC=CC=1[Se][Se]C1=CC=CC=C1 YWWZCHLUQSHMCL-UHFFFAOYSA-N 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- CEWDRCQPGANDRS-UHFFFAOYSA-N 1-ethenyl-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(C=C)C=C1 CEWDRCQPGANDRS-UHFFFAOYSA-N 0.000 claims description 3
- JCHJBEZBHANKGA-UHFFFAOYSA-N 1-methoxy-3,5-dimethylbenzene Chemical compound COC1=CC(C)=CC(C)=C1 JCHJBEZBHANKGA-UHFFFAOYSA-N 0.000 claims description 3
- QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 claims description 3
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 3
- 238000003818 flash chromatography Methods 0.000 claims description 3
- HDBWAWNLGGMZRQ-UHFFFAOYSA-N p-Vinylbiphenyl Chemical compound C1=CC(C=C)=CC=C1C1=CC=CC=C1 HDBWAWNLGGMZRQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- 238000010791 quenching Methods 0.000 claims description 3
- 239000000741 silica gel Substances 0.000 claims description 3
- 229910002027 silica gel Inorganic materials 0.000 claims description 3
- 238000003828 vacuum filtration Methods 0.000 claims description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical group Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 2
- CRNDQFASPYBRPT-UHFFFAOYSA-N 1-bromo-4-(4-bromophenyl)seleninylbenzene Chemical compound C1=CC(Br)=CC=C1[Se](=O)C1=CC=C(Br)C=C1 CRNDQFASPYBRPT-UHFFFAOYSA-N 0.000 claims 1
- RWAZHGCKYYGQJA-UHFFFAOYSA-N 1-chloro-4-(4-chlorophenyl)seleninylbenzene Chemical compound C1=CC(Cl)=CC=C1[Se](=O)C1=CC=C(Cl)C=C1 RWAZHGCKYYGQJA-UHFFFAOYSA-N 0.000 claims 1
- SXEWETDJNQVWQY-UHFFFAOYSA-N 1-methoxy-4-(4-methoxyphenyl)seleninylbenzene Chemical compound C1=CC(OC)=CC=C1[Se](=O)C1=CC=C(OC)C=C1 SXEWETDJNQVWQY-UHFFFAOYSA-N 0.000 claims 1
- SSHNCKVJNHOUCT-UHFFFAOYSA-N 1-methyl-4-(4-methylphenyl)seleninylbenzene Chemical compound C1=CC(C)=CC=C1[Se](=O)C1=CC=C(C)C=C1 SSHNCKVJNHOUCT-UHFFFAOYSA-N 0.000 claims 1
- 239000011669 selenium Substances 0.000 abstract description 17
- 229910052711 selenium Inorganic materials 0.000 abstract description 5
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 abstract description 4
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 238000005580 one pot reaction Methods 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 91
- 239000000047 product Substances 0.000 description 33
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 32
- 238000005160 1H NMR spectroscopy Methods 0.000 description 32
- 238000012512 characterization method Methods 0.000 description 32
- 239000007788 liquid Substances 0.000 description 32
- 239000011734 sodium Substances 0.000 description 18
- PUCVISUAFAYNFY-UHFFFAOYSA-N O=[Se](C1=CC=CC=C1)(C1=CC=CC=C1)=[Se] Chemical compound O=[Se](C1=CC=CC=C1)(C1=CC=CC=C1)=[Se] PUCVISUAFAYNFY-UHFFFAOYSA-N 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- QMIDCDJPXYIPFL-UHFFFAOYSA-N 1-(trifluoromethyl)-4-[4-(trifluoromethyl)phenyl]selanylbenzene Chemical compound C1=CC(C(F)(F)F)=CC=C1[Se]C1=CC=C(C(F)(F)F)C=C1 QMIDCDJPXYIPFL-UHFFFAOYSA-N 0.000 description 2
- OIDHAGXJXBHQHF-UHFFFAOYSA-N 1-bromo-4-(4-bromophenyl)selanylbenzene Chemical compound C1=CC(Br)=CC=C1[Se]C1=CC=C(Br)C=C1 OIDHAGXJXBHQHF-UHFFFAOYSA-N 0.000 description 2
- YYYHAXIKLYPYBS-UHFFFAOYSA-N 1-chloro-2-(2-chlorophenyl)selanylbenzene Chemical compound ClC1=CC=CC=C1[Se]C1=CC=CC=C1Cl YYYHAXIKLYPYBS-UHFFFAOYSA-N 0.000 description 2
- XHKOOXRNSLBNDR-UHFFFAOYSA-N 1-chloro-4-(4-chlorophenyl)selanylbenzene Chemical compound C1=CC(Cl)=CC=C1[Se]C1=CC=C(Cl)C=C1 XHKOOXRNSLBNDR-UHFFFAOYSA-N 0.000 description 2
- WELPMJSCPKDRLC-UHFFFAOYSA-N 1-fluoro-4-(4-fluorophenyl)selanylbenzene Chemical compound C1=CC(F)=CC=C1[Se]C1=CC=C(F)C=C1 WELPMJSCPKDRLC-UHFFFAOYSA-N 0.000 description 2
- LURBCACEKXUJEG-UHFFFAOYSA-N 1-methoxy-4-(4-methoxyphenyl)selanylbenzene Chemical compound C1=CC(OC)=CC=C1[Se]C1=CC=C(OC)C=C1 LURBCACEKXUJEG-UHFFFAOYSA-N 0.000 description 2
- RUGKJOXEVZASTC-UHFFFAOYSA-N 1-methyl-3-(3-methylphenyl)selanylbenzene Chemical compound CC1=CC=CC([Se]C=2C=C(C)C=CC=2)=C1 RUGKJOXEVZASTC-UHFFFAOYSA-N 0.000 description 2
- OAJSCXNYCHQGTF-UHFFFAOYSA-N 1-methyl-4-(4-methylphenyl)selanylbenzene Chemical compound C1=CC(C)=CC=C1[Se]C1=CC=C(C)C=C1 OAJSCXNYCHQGTF-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C391/00—Compounds containing selenium
- C07C391/02—Compounds containing selenium having selenium atoms bound to carbon atoms of six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明公开了一种芳基硒醚类化合物及其合成方法，所述合成方法包括以下步骤：将苯乙烯和/或苯乙烯衍生物、富电子芳烃、以及二硒醚溶解在有机溶剂中，混合均匀；加入催化剂，在在小于所述有机溶剂的沸点温度条件下进行反应，反应完成获得所述芳基硒醚类化合物。本发明利用催化剂催化苯乙烯或苯乙烯衍生物的傅克烷基硒化反应，一锅法合成含硒化合物，能够以良好至很高的收率得到产物，并且底物范围宽，在克级反应中也有不错收率。
Description
技术领域
本发明涉及有机合成技术领域，特别涉及一种芳基硒醚类化合物及其合成方法。
背景技术
含硒化合物在有机合成、药物化学、材料科学和生物化学等方面具有重要的作用。此外，有机硒化合物是有机合成中用途广泛的中间体，具有广泛的生物学性质，可作为亲电试剂、亲核试剂、有机合成催化剂和配体。因此，研究人员利用硒各方面的特点，合成了一系列表现出不同药理活性的含硒化合物，这类化合物可作为抗氧化剂、酶模拟物和抑制剂、免疫调节剂、细胞保护剂、抗肿瘤、抗炎、抗高血压和抗感染剂等等。基于含硒化合物的重要性，我们对合成芳基硒醚类化合物的兴趣日益浓厚。
发明内容
针对上述问题，本发明旨在提供一种芳基硒醚类化合物及其合成方法。
本发明的技术方案如下：
一方面，提供一种芳基硒醚类化合物的合成方法，包括以下步骤：
将苯乙烯和/或苯乙烯衍生物、富电子芳烃、以及二硒醚溶解在有机溶剂中，混合均匀；
加入催化剂，在在小于所述有机溶剂的沸点温度条件下进行反应，反应完成获得所述芳基硒醚类化合物。
作为优选，所述有机溶剂为乙腈，所述催化剂为氯化铁，所述反应的温度为80℃，时间为12h；所述芳基硒醚类化合物的反应通式如下所示：
式中：R1为芳基，Ar为甲氧基苯、苯酚和吲哚中的一种，R2为芳基。
作为优选，所述苯乙烯衍生物为4-甲基苯乙烯、4-叔丁基苯乙烯、4-苯基苯乙烯、4-三氟甲基苯乙烯、4-氟苯乙烯、4-氯苯乙烯、4-溴苯乙烯中的任意一种或多种。
作为优选，所述富电子芳烃为1,3,5-三甲氧基苯、1,2,4-三甲氧基苯、间甲氧基苯、邻甲氧基苯、3,5-二甲基苯甲醚、3,4,5-三甲氧基甲苯、3,4,5-三甲氧基苯酚、吲哚中的任意一种或多种。
作为优选，所述二硒醚为二苯基二硒醚、双(4-甲苯基)硒醚、双(4-甲氧苯基)硒醚、双(4-三氟甲苯基)硒醚、双(4-氟苯基)硒醚、双(4-氯苯基)硒醚、双(4-溴苯基)硒醚、双(2-氯苯基)硒醚、双(3-甲苯基)硒醚中的任意一种或多种。
作为优选，还包括利用薄板层析检测反应是否完成的步骤。
作为优选，反应完成后还包括以下步骤：待反应混合物冷却至室温，加入饱和氯化钠溶液淬灭所述反应混合物；然后用乙酸乙酯萃取所述反应混合物，接着对所述反应混合物进行干燥、真空过滤浓缩；得到的残渣利用硅胶闪色谱纯化，最后用石油醚或乙酸乙酯洗脱得到所述芳基硒醚类化合物。
另一方面，还提供一种芳基硒醚类化合物，采用上述任意一项所述的芳基硒醚类化合物的合成方法制备而成。
本发明的有益效果是：
本发明通过在有机溶剂中，利用催化剂催化苯乙烯和/或苯乙烯衍生物、富电子芳烃、以及二硒醚发生三组分反应，一步完成芳基硒醚类化合物的合成。
具体实施方式
下面结合实施例对本发明进一步说明。需要说明的是，在不冲突的情况下，本申请中的实施例及实施例中的技术特征可以相互结合。需要指出的是，除非另有指明，本申请使用的所有技术和科学术语具有与本申请所属技术领域的普通技术人员通常理解的相同含义。本发明公开使用的“包括”或者“包含”等类似的词语意指出现该词前面的元件或者物件涵盖出现在该词后面列举的元件或者物件及其等同，而不排除其他元件或者物件。
实施例1
在设有搅拌装置的反应容器中加入苯乙烯(0.5mmol)，1,3,5-三甲氧基苯(0.60mmol)，二苯基二硒醚(0.5mmol)，FeCl3(0.1mmol)和MeCN(4.0mL)。为了避免有机溶剂的蒸发，将所述反应容器密封，若采用敞口的反应容器则在空气气氛下用橡胶隔膜封闭反应容器的敞口。将反应容器置于80℃条件下反应12小时，通过TLC检查反应进展，确认反应完成。冷却至室温后，加入饱和NaCl溶液(10mL)淬灭反应混合物。用乙酸乙酯(15mL×3)萃取反应混合物。组合有机相在无水MgSO4上干燥，在旋转蒸发器上真空过滤浓缩。残渣经硅胶闪色谱纯化，用石油醚/乙酸乙酯洗脱得到相应的黄色黏性液体苯基(2-苯基-2-(2,4,6-三甲氧基苯基)乙基)硒烷，产率为88％，反应方程式如下所示：
该产物的结构表征数据如下所示：
1H NMR(400MHz,CDCl3)δ＝7.41–7.32(m,2H),7.24(d,J＝7.3,2H),7.18–7.09(m,5H),7.08–7.01(m,1H),6.01(s,2H),4.85(dd,J＝9.5,7.1,1H),3.84–3.78(m,1H),3.70(s,3H),3.67–3.59(m,7H)；
13C NMR(75MHz,Chloroform-d)δ＝159.88,159.17,144.24,132.52,131.37,128.66,127.83,127.74,126.28,125.62,112.40,91.13,55.58,55.14,40.18,31.48；
HRMS(ESI):calculated for C23H24O3SeNa[M+Na]+＝451.0787,found 451.0783。
实施例2
与实施例1不同的是，本实施例中的富电子芳烃采用1,2,4-三甲氧基苯，得到黄色粘稠状液体苯基(2-苯基-2-(2,4,5-三甲氧基苯基)乙基)硒烷，产率为84％，该产物的结构表征数据如下所示：
1H NMR(400MHz,CDCl3)δ＝7.39(dt,J＝5.1,3.0,2H),7.23–7.10(m,8H),6.59(s,1H),6.41(s,1H),4.60(t,J＝8.1,1H),3.78(s,3H),3.66(d,J＝10.2,6H),3.54–3.41(m,2H)；
13C NMR(75MHz,Chloroform-d)δ＝151.32,148.31,143.36,142.89,132.53,131.07,128.81,128.23,127.91,126.57,126.31,123.51,112.65,97.94,56.70,56.34,56.00,44.24,32.73；
HRMS(ESI):calculated for C23H24O3SeNa[M+Na]+＝451.0791,found 451.0783。
实施例3
与实施例1不同的是，本实施例中的富电子芳烃采用间二甲氧基苯，得到黄色粘稠状液体(2-(2,4-二甲氧基苯基)-2-苯基乙基)(苯基)硒烷，产率为74％，该产物的结构表征数据如下所示：
1H NMR(400MHz,CDCl3)δ＝7.56–7.44(m,2H),7.32–7.21(m,8H),7.11–7.02(m,1H),6.59–6.31(m,2H),4.77–4.62(m,1H),3.82–3.75(m,6H),3.66–3.50(m,2H)；
13C NMR(75MHz,Chloroform-d)δ＝159.44,157.82,143.42,132.40,131.18,128.81,128.34,128.19,128.04,126.49,126.24,124.46,103.91,98.66,55.24,55.17,44.02,32.73；
HRMS(ESI):calculated for C22H23O2Se[M+H]+＝399.0860,found 399.0858。
实施例4
与实施例1不同的是，本实施例中的富电子芳烃采用邻二甲氧基苯，得到黄色粘稠状液体(2-(3,4-二甲氧基苯基)-2-苯基乙基)(苯基)硒烷，产率为54％，该产物的结构表征数据如下所示：
1H NMR(400MHz,CDCl3)δ＝7.53–7.43(m,2H),7.33–7.30(m,2H),7.29–7.23(m,6H),6.86–6.81(m,2H),6.73(s,1H),4.25(t,J＝8.0,1H),3.88–3.83(m,6H),3.62–3.56(m,2H)；
13C NMR(75MHz,Chloroform-d)δ＝148.81,147.71,143.77,135.94,132.63,128.97,128.47,127.60,126.80,126.59,119.58,111.31,111.02,55.76,51.12,33.90；
HRMS(ESI):calculated for C22H22O2SeNa[M+Na]+＝421.0683,found 421.0677。
实施例5
与实施例1不同的是，本实施例中的富电子芳烃采用3,5-二甲基苯甲醚，得到无色油状液体(2-(4-甲氧基-2,6-二甲基苯基)-2-苯基乙基)(苯基)硒烷，产率为72％，该产物的结构表征数据如下所示：
1H NMR(400MHz,CDCl3)δ＝7.40–7.31(m,2H),7.20–7.10(m,7H),7.08–7.03(m,1H),6.49(d,J＝11.9,1H),6.43(s,1H),4.55(t,J＝7.8,1H),3.81(dd,J＝11.7,9.0,1H),3.69(dd,J＝11.7,7.2,1H),3.53(s,3H),2.19(s,3H),2.10(s,3H)；
13C NMR(75MHz,Chloroform-d)δ＝158.17,143.58,137.69,137.20,132.54,131.07,128.84,127.89,127.73,126.49,125.76,124.06,110.61,55.12,44.11,31.58,21.32,20.71；
HRMS(ESI):calculated for C23H25OSe[M+H]+＝397.1077,found 397.1065。
实施例6
与实施例1不同的是，本实施例中的富电子芳烃采用3,4,5-三甲氧基甲苯，得到白色粘稠状液体苯基(2-苯基-2-(2,3,4-三甲氧基-6-甲基苯基)乙基)硒烷，产率为80％，该产物的结构表征数据如下所示：
1H NMR(300MHz,CDCl3)δ＝7.50(dd,J＝6.4,3.1,2H),7.30(d,J＝4.3,4H),7.22(ddd,J＝13.0,6.7,3.0,4H),4.64(t,J＝7.7,1H),3.94–3.85(m,4H),3.82–3.75(m,4H),3.38(s,3H),2.26(s,3H)；
13C NMR(75MHz,Chloroform-d)δ＝152.55,151.83,143.81,140.58,132.50,131.84,131.06,128.88,128.23,127.94,127.48,126.58,125.73,109.10,60.40,59.84,55.68,43.77,31.23,20.94；
HRMS(ESI):calculated for C24H25O3SeNa[M+Na]+＝465.0946,found 465.0939。
实施例7
与实施例1不同的是，本实施例中的富电子芳烃采用3,4,5-三甲氧基苯酚，得到暗红色粘稠状液体3,4,5-三甲氧基-2-(1-苯基-2-(苯基硒基)乙基)苯酚，产率为79％，该产物的结构表征数据如下所示：
1H NMR(400MHz,DMSO-d6)δ＝9.42(s,1H),7.49–7.44(m,2H),7.39–7.34(m,2H),7.29–7.20(m,5H),7.16–7.11(m,1H),6.30(s,1H),4.78–4.72(m,1H),3.92(dd,J＝11.4,9.2,1H),3.77(dd,J＝11.4,7.3,1H),3.72(s,3H),3.63(s,3H),3.54(s,3H)；
13C NMR(101MHz,Chloroform-d)δ＝152.67,152.49,150.30,143.46,136.25,132.57,131.03,128.97,128.36,127.81,126.69,126.31,116.11,96.84,60.86,60.73,55.77,41.22,31.15；
HRMS(ESI):calculated for C23H24O4SeNa[M+Na]+＝467.0734,found 467.0733。
实施例8
与实施例1不同的是，本实施例采用4-甲基苯乙烯代替实施例1中的苯乙烯，得到黄色粘稠状液体苯基(2-(对甲苯基)-2-(2,4,6-三甲氧基苯基)乙基)硒烷，产率为56％，该产物的结构表征数据如下所示：
1H NMR(400MHz,CDCl3)δ＝7.53–7.40(m,2H),7.27–7.10(m,6H),7.05–6.95(m,1H),6.15–6.07(m,2H),4.92(dd,J＝9.7,7.0,1H),3.93–3.87(m,1H),3.84–3.80(m,3H),3.78–3.66(m,7H),2.32–2.29(m,3H)；
13C NMR(75MHz,Chloroform-d)δ＝159.82,159.21,144.12,137.12,132.49,128.65,127.62,126.45,126.24,124.83,112.36,91.14,55.60,55.14,40.13,31.60,21.53；
HRMS(ESI):calculated for C24H27O3Se[M+H]+＝443.1120,found 443.1120。
实施例9
与实施例1不同的是，本实施例采用4-叔丁基苯乙烯代替实施例1中的苯乙烯，得到黄色粘稠状液体(2-(4-(叔丁基)苯基)-2-(2,4,6-三甲氧基苯基)乙基)(苯基)硒烷，产率为51％，该产物的结构表征数据如下所示：
1H NMR(400MHz,Chloroform-d)δ＝7.47–7.28(m,2H),7.23–7.01(m,8H),6.01(s,2H),4.82(dd,J＝10.0,6.7,1H),3.85(dd,J＝11.4,10.0,1H),3.68(s,3H),3.63–3.53(m,4H),1.19(s,9H)；
13C NMR(101MHz,Chloroform-d)δ＝159.87,159.32,148.32,141.28,132.62,131.52,128.71,127.50,126.31,124.77,112.40,91.20,55.68,55.22,39.98,34.31,31.94,31.43；
HRMS(ESI):calculated for C27H32O3SeNa[M+Na]+＝507.1411,found 507.1411。
实施例10
与实施例1不同的是，本实施例采用4-苯基苯乙烯代替实施例1中的苯乙烯，得到黄色粘稠状液体(2-([[1,1'-联苯]-4-基]-2-(2,4,6-三甲氧基苯基)乙基)(苯基)硒烷，产率为47％，该产物的结构表征数据如下所示：
1H NMR(400MHz,CDCl3)δ＝7.53–7.40(m,2H),7.27–7.10(m,6H),7.05–6.95(m,1H),6.15–6.07(m,2H),4.92(dd,J＝9.7,7.0,1H),3.93–3.87(m,1H),3.84–3.80(m,3H),3.78–3.66(m,7H),2.32–2.29(m,3H)；
13C NMR(75MHz,Chloroform-d)δ＝160.09,159.31,143.55,141.29,138.61,132.71,131.47,128.85,128.75,128.42,127.05,126.98,126.66,126.48,112.36,91.28,55.75,55.29,40.11,31.62；
HRMS(ESI):calculated for C29H28O3SeNa[M+Na]+＝527.1091,found 527.1096。
实施例11
与实施例1不同的是，本实施例采用4-三氟甲基苯乙烯代替实施例1中的苯乙烯，得到黄色粘稠状液体苯基(2-(4-(三氟甲基)苯基)-2-(2,4,6-三甲氧基苯基)乙基)硒烷，产率为70％，该产物的结构表征数据如下所示：
1H NMR(400MHz,CDCl3)δ＝7.54–7.40(m,6H),7.28–7.21(m,3H),6.12(s,2H),4.99(t,J＝8.2,1H),3.90–3.80(m,4H),3.79–3.70(m,7H)；
13C NMR(75MHz,Chloroform-d)δ＝160.18,158.95,148.31,132.66,130.86,128.71,128.16,127.46,126.49,124.58,124.53,111.58,90.99,55.45,55.07,40.07,30.74；
HRMS(ESI):calculated for C24H24F3O3Se[M+H]+＝497.0841,found 497.0838。
实施例12
与实施例1不同的是，本实施例采用4-氟苯乙烯代替实施例1中的苯乙烯，得到黄色粘稠状液体(2-(4-氟苯基)-2-(2,4,6-三甲氧基苯基)乙基)(苯基)硒烷，产率为76％，该产物的结构表征数据如下所示：
1H NMR(400MHz,CDCl3)δ＝7.47–7.40(m,2H),7.30–7.19(m,5H),6.94–6.84(m,2H),6.09(s,2H),4.93–4.83(m,1H),3.85–3.77(m,4H),3.73–3.65(m,7H)；
13C NMR(75MHz,Chloroform-d)δ＝162.50,159.87,159.28,158.88,139.77,132.45,131.03,129.25,129.15,128.62,126.29,114.41,114.13,112.08,90.96,55.42,54.99,39.44,31.33；
HRMS(ESI):calculated for C23H24FO3Se[M+H]+＝447.0856,found 447.0870。
实施例13
与实施例1不同的是，本实施例采用4-氟苯乙烯代替实施例1中的苯乙烯，1,2,4-三甲氧基苯代替实施例1中的1,3,5-三甲氧基苯，得到黄色粘稠状液体(2-(4-氟苯基)-2-(2,4,5-三甲氧基苯基)乙基)(苯基)硒烷，产率为67％，该产物的结构表征数据如下所示：
1H NMR(400MHz,CDCl3)δ＝7.47–7.32(m,2H),7.15(dddd,J＝11.5,8.4,5.6,2.6,5H),6.94–6.83(m,2H),6.56(s,1H),6.41(s,1H),4.55(t,J＝8.1,1H),3.79(s,3H),3.67(d,J＝13.2,6H),3.52–3.36(m,2H)；
13C NMR(75MHz,Chloroform-d)δ＝162.94,159.70,151.20,148.38,142.84,139.01,132.61,130.83,129.38(d,J＝7.8),128.86,126.69,123.24,114.99(d,J＝21.1),112.39,97.79,56.72,56.26,55.99,43.65,32.72；
HRMS(ESI):calculated for C23H23FO3SeNa[M+Na]+＝469.0673,found 469.0689。
实施例14
与实施例1不同的是，本实施例采用4-氟苯乙烯代替实施例1中的苯乙烯，3,4,5-三甲氧基甲苯代替实施例1中的1,3,5-三甲氧基苯，得到白色粘稠状液体(2-(4-氟苯基)-2-(2,3,4-三甲氧基-6-甲基苯基)乙基)(苯基)硒烷，产率为60％，该产物的结构表征数据如下所示：
1H NMR(400MHz,Chloroform-d)δ＝7.42–7.33(m,2H),7.15(qd,J＝5.1,4.5,2.5,5H),6.90–6.85(m,2H),6.37(s,1H),4.45(t,J＝6.9,1H),3.76–3.73(m,4H),3.69(s,3H),3.62(dd,J＝11.8,8.2,1H),3.31(s,3H),2.13(s,3H)；
13C NMR(75MHz,Chloroform-d)δ＝161.02(d,J＝244.2),152.45,151.93,140.57,139.41,132.65,131.68,130.79,128.95,128.29(d,J＝7.5),127.92,126.74,114.66(d,J＝21.0),109.10,60.44,59.94,55.69,43.28,31.36,20.90；
HRMS(ESI):calculated for C24H25FO3SeNa[M+Na]+＝483.0858,found 483.0845。
实施例15
与实施例1不同的是，本实施例采用4-氟苯乙烯代替实施例1中的苯乙烯，3,5-二甲氧基苯甲醚代替实施例1中的1,3,5-三甲氧基苯，得到无色油状液体(2-(4-氟苯基)-2-(4-甲氧基-2,6-二甲基苯基)乙基)(苯基)硒烷，产率为56％，该产物的结构表征数据如下所示：
1H NMR(400MHz,CDCl3)δ＝7.40–7.31(m,2H),7.18–7.10(m,5H),6.88–6.79(m,2H),6.55–6.49(m,1H),6.43(s,1H),4.49(t,J＝7.5,1H),3.75(dd,J＝11.8,8.5,1H),3.69–3.61(m,1H),3.55(s,3H),2.20(s,3H),2.09(s,3H)；
13C NMR(75MHz,Chloroform-d)δ＝160.99(d,J＝243.8),157.97,139.15(d,J＝2.9),137.40,137.26,132.61,130.78,129.19,129.09,128.82,126.54,124.04,114.63,114.35,110.56,54.96,43.51,31.54,21.24,20.59；
HRMS(ESI):calculated for C23H23FNaOSe[M+Na]+＝437.0788,found 437.0791。
实施例16
与实施例1不同的是，本实施例采用4-氯苯乙烯代替实施例1中的苯乙烯，得到黄色粘稠状液体(2-(4-氯苯基)-2-(2,4,6-三甲氧基苯基)乙基)(苯基)硒烷，产率为87％，该产物的结构表征数据如下所示：
1H NMR(400MHz,CDCl3)δ＝7.38–7.32(m,2H),7.18–7.08(m,7H),6.01(s,2H),4.84–4.75(m,1H),3.70(d,J＝4.6,4H),3.64–3.58(m,7H)；
13C NMR(75MHz,Chloroform-d)δ＝160.04,158.99,142.68,132.61,131.20,131.07,129.27,128.71,127.77,126.42,112.01,91.08,55.56,55.16,39.62,31.12；
HRMS(ESI):calculated for C23H23ClO3SeNa[M+Na]+＝485.0390,found485.0394。
实施例17
与实施例1不同的是，本实施例采用4-氯苯乙烯代替实施例1中的苯乙烯，1,2,4-三甲氧基苯代替实施例1中的1,3,5-三甲氧基苯，得到黄色粘稠状液体(2-(4-氯苯基)-2-(2,4,5-三甲氧基苯基)乙基)(苯基)硒烷，产率为76％，该产物的结构表征数据如下所示：
1H NMR(300MHz,CDCl3)δ＝7.52–7.45(m,2H),7.29–7.19(m,7H),6.68(s,1H),6.51(s,1H),4.65(t,J＝8.0,1H),3.88(s,3H),3.76(d,J＝16.3,6H),3.63–3.46(m,2H)；
13C NMR(75MHz,Chloroform-d)δ＝151.16,148.43,142.82,141.83,132.57,131.83,130.64,129.24,128.78,128.21,126.63,122.86,112.45,97.78,56.69,56.13,55.92,43.75,32.35；
HRMS(ESI):calculated for C23H23ClO3SeNa[M+Na]+＝485.0388,found485.0394。
实施例18
与实施例1不同的是，本实施例采用4-氯苯乙烯代替实施例1中的苯乙烯，3,4,5-三甲氧基甲苯代替实施例1中的1,3,5-三甲氧基苯，得到白色粘稠状液体(2-(4-氯苯基)-2-(2,3,4-三甲氧基-6-甲基苯基)乙基)(苯基)硒烷，产率为70％，该产物的结构表征数据如下所示：
1H NMR(400MHz,CDCl3)δ＝7.43–7.34(m,2H),7.18–7.10(m,7H),6.37(s,1H),4.43(s,1H),3.77–3.67(m,7H),3.60(dd,J＝11.8,8.1,1H),3.29(d,J＝18.2,3H),2.12(s,3H)；
13C NMR(75MHz,Chloroform-d)δ＝152.48,152.06,142.34,140.62,132.78,131.74,131.48,130.76,129.00,128.05,127.73,126.84,124.24,109.18,60.49,60.00,55.76,43.43,31.16,20.92；
HRMS(ESI):calculated for C24H26ClO3Se[M+H]+＝477.0735,found 477.0730。
实施例19
与实施例1不同的是，本实施例采用4-氯苯乙烯代替实施例1中的苯乙烯，3,5-二甲氧基苯甲醚代替实施例1中的1,3,5-三甲氧基苯，得到无色油状液体(2-(4-氯苯基)-2-(4-甲氧基-2,6-二甲基苯基)乙基)(苯基)硒烷，产率为67％，该产物的结构表征数据如下所示：
1H NMR(400MHz,CDCl3)δ＝7.49–7.42(m,2H),7.28–7.18(m,7H),6.62(s,1H),6.52(s,1H),4.58(t,J＝7.6,1H),3.86–3.73(m,2H),3.64(s,3H),2.30(s,3H),2.19(s,3H)；
13C NMR(75MHz,Chloroform-d)δ＝158.02,142.06,137.48,132.73,131.40,130.75,129.16,128.90,127.92,126.67,126.58,124.09,110.60,55.07,43.62,31.29,21.31,20.65；
HRMS(ESI):calculated for C23H23ClOSeNa[M+Na]+＝453.0493,found 453.0495。
实施例20
与实施例1不同的是，本实施例采用4-溴苯乙烯代替实施例1中的苯乙烯，得到黄色粘稠状液体(2-(4-溴苯基)-2-(2,4,6-三甲氧基苯基)乙基)(苯基)硒烷，产率为90％，该产物的结构表征数据如下所示：
1H NMR(400MHz,CDCl3)δ＝7.42–7.30(m,2H),7.30–7.20(m,2H),7.14(ddt,J＝11.7,9.5,4.8,5H),6.00(s,2H),4.84–4.71(m,1H),3.75–3.68(m,4H),3.66–3.57(m,7H)；
13C NMR(75MHz,CDCl3)δ＝160.03(s),158.96(s),143.20(s),132.60(s),131.03(s),130.69(s),129.68(s),128.69(s),126.41(s),119.31(s),111.90(s),91.06(s),55.53(s),55.14(s),39.67(s),31.01(s)；
HRMS(ESI):calculated for C23H24BrO3Se[M+H]+＝507.0074,found 507.0069。
实施例21
与实施例1不同的是，本实施例采用4-溴苯乙烯代替实施例1中的苯乙烯，1,2,4-三甲氧基苯代替实施例1中的1,3,5-三甲氧基苯，得到黄色粘稠状液体(2-(4-溴苯基)-2-(2,4,5-三甲氧基苯基)乙基)(苯基)硒烷，产率为76％，该产物的结构表征数据如下所示：
1H NMR(400MHz,CDCl3)δ＝7.44–7.26(m,4H),7.19–7.14(m,3H),7.08–7.00(m,2H),6.56(s,1H),6.40(s,1H),4.52(t,J＝8.1,1H),3.79(s,3H),3.66(d,J＝18.5,6H),3.51–3.34(m,2H)；
13C NMR(75MHz,Chloroform-d)δ＝151.23,148.50,142.87,142.42,132.68,131.27,130.71,129.72,128.88,126.75,122.82,120.09,112.41,97.77,56.78,56.24,56.02,43.90,32.37；
HRMS(ESI):calculated for C23H23BrO3SeNa[M+Na]+＝528.9870,found528.9888。
实施例22
与实施例1不同的是，本实施例采用4-溴苯乙烯代替实施例1中的苯乙烯，3,4,5-三甲氧基甲苯代替实施例1中的1,3,5-三甲氧基苯，得到白色粘稠状液体(2-(4-溴苯基)-2-(2,3,4-三甲氧基-6-甲基苯基)乙基)(苯基)硒烷，产率为74％，该产物的结构表征数据如下所示：
1H NMR(400MHz,CDCl3)δ＝7.38–7.33(m,2H),7.28(d,J＝8.5,2H),7.14–7.10(m,3H),7.04(d,J＝8.3,2H),6.35(s,1H),4.40(s,1H),3.74–3.68(m,4H),3.67(s,3H),3.61–3.54(m,1H),3.29(s,3H),2.10(s,3H)；
13C NMR(75MHz,Chloroform-d)δ＝152.39,152.00,142.82,140.52,132.71,131.67,130.93,130.67,129.36,128.95,127.58,126.78,119.47,109.09,60.42,59.93,55.69,43.41,31.00,20.88；
HRMS(ESI):calculated for C24H25BrO3SeNa[M+Na]+＝543.0035,found543.0045。
实施例23
与实施例1不同的是，本实施例采用4-溴苯乙烯代替实施例1中的苯乙烯，3,5-二甲氧基苯甲醚代替实施例1中的1,3,5-三甲氧基苯，得到无色油状液体(2-(4-溴苯基)-2-(4-甲氧基-2,6-二甲基苯基)乙基)(苯基)硒烷，产率为68％，该产物的结构表征数据如下所示：
1H NMR(400MHz,CDCl3)δ＝7.38–7.31(m,2H),7.29–7.22(m,2H),7.18–7.12(m,3H),7.06(d,J＝8.3,2H),6.53–6.39(m,2H),4.45(d,J＝6.9,1H),3.75–3.62(m,2H),3.53(s,3H),2.19(s,3H),2.08(s,3H)；
13C NMR(75MHz,Chloroform-d)δ＝158.11,142.70,137.59,132.85,130.98,130.85,129.69,129.01,126.79,126.61,124.20,119.63,110.70,55.17,43.90–43.67(m),31.31,21.44,20.78；
HRMS(ESI):calculated for C23H23BrOSeNa[M+Na]+＝496.9985,found 496.9990。
实施例24
与实施例1不同的是，本实施例采用双(4-甲苯基)硒醚代替实施例1中的二苯基二硒醚烯，得到黄色粘稠状液体(2-苯基-2-(2,4,6-三甲氧基苯基)乙基)(对甲苯基)硒烷，产率为82％，该产物的结构表征数据如下所示：
1H NMR(400MHz,CDCl3)δ＝7.28–7.11(m,6H),7.07–7.01(m,1H),6.99–6.90(m,2H),6.01(d,J＝6.6,2H),4.91–4.75(m,1H),3.81–3.74(m,1H),3.72–3.69(m,3H),3.65–3.56(m,7H),2.27–2.19(m,3H)；
13C NMR(75MHz,Chloroform-d)δ＝159.76,159.05,144.23,136.14,132.93,129.40,127.74,127.63,127.31,125.49,112.29,90.98,55.45,55.00,40.12,31.77,20.92；
HRMS(ESI):calculated for C24H27O3Se[M+H]+＝443.1116,found 443.1120。
实施例25
与实施例1不同的是，本实施例采用双(4-甲氧苯基)硒醚代替实施例1中的二苯基二硒醚烯，得到黄色粘稠状液体(2-苯基-2-(2,4,6-三甲氧基苯基)乙基)(对甲氧苯基)硒烷，产率为69％，该产物的结构表征数据如下所示：
1H NMR(400MHz,CDCl3)δ＝7.38–7.26(m,2H),7.22(d,J＝7.4,2H),7.13(dd,J＝10.3,4.8,2H),7.03(t,J＝7.2,1H),6.74–6.64(m,2H),6.01(s,2H),4.87–4.72(m,1H),3.78–3.68(m,7H),3.65–3.59(m,6H),3.52(dt,J＝11.9,5.9,1H)；
13C NMR(75MHz,Chloroform-d)δ＝159.76,159.09,158.84,144.31,135.44,127.78,127.66,125.51,120.91,114.30,112.31,91.00,55.49,55.12,55.06,40.25,32.60；
HRMS(ESI):calculated for C24H27O4Se[M+H]+＝459.1076,found 459.1070。
实施例26
与实施例1不同的是，本实施例采用双(4-三氟甲苯基)硒醚代替实施例1中的二苯基二硒醚烯，得到黄色粘稠状液体(2-苯基-2-(2,4,6-三甲氧基苯基)乙基)(对三氟甲苯基)硒烷，产率为75％，该产物的结构表征数据如下所示：
1H NMR(400MHz,Chloroform-d)δ＝7.43–7.30(m,4H),7.24(dd,J＝8.0,1.4,2H),7.14(t,J＝7.6,2H),7.09–7.02(m,1H),5.99(s,2H),4.85(dd,J＝9.6,7.0,1H),3.85(dd,J＝11.6,9.6,1H),3.70–3.65(m,4H),3.60(s,6H)；
13C NMR(75MHz,Chloroform-d)δ＝160.00,159.04,143.84,137.01,131.46,129.86,127.78,127.73,125.75,125.18(q,J＝3.9),122.42,111.85,90.95,55.43,55.00,39.97,30.90；
HRMS(ESI):calculated for C24H24F3O3Se[M+H]+＝497.0838,found 497.0838。
实施例27
与实施例1不同的是，本实施例采用双(4-氟苯基)硒醚代替实施例1中的二苯基二硒醚烯，得到黄色粘稠状液体(2-苯基-2-(2,4,6-三甲氧基苯基)乙基)(对氟苯基)硒烷，产率为70％，该产物的结构表征数据如下所示：
1H NMR(400MHz,CDCl3)δ＝7.39–7.27(m,2H),7.22(d,J＝7.2,2H),7.16–7.12(m,2H),7.05(ddd,J＝7.2,5.9,1.2,1H),6.89–6.78(m,2H),6.01(d,J＝4.8,2H),4.80(dd,J＝9.7,7.0,1H),3.80–3.74(m,1H),3.70(d,J＝4.1,3H),3.63–3.54(m,7H)；
13C NMR(75MHz,Chloroform-d)δ＝161.99(d,J＝245.9),159.86,159.07,144.11,135.28,135.18,127.76,127.72,125.62,125.37(d,J＝3.3),115.79,115.51,112.10,91.00,55.48,55.07,40.21,32.32；
HRMS(ESI):calculated for C23H23FO3SeK[M+K]+＝485.0452,found 485.0429。
实施例28
与实施例1不同的是，本实施例采用双(4-氯苯基)硒醚代替实施例1中的二苯基二硒醚烯，得到黄色粘稠状液体(2-苯基-2-(2,4,6-三甲氧基苯基)乙基)(对氯苯基)硒烷，产率为76％，该产物的结构表征数据如下所示：
1H NMR(400MHz,CDCl3)δ＝7.25(ddd,J＝16.6,9.2,4.9,4H),7.17–7.04(m,5H),6.01(d,J＝5.7,2H),4.81(dd,J＝9.6,7.0,1H),3.82–3.76(m,1H),3.70(d,J＝4.6,3H),3.64–3.58(m,7H)；
13C NMR(75MHz,Chloroform-d)δ＝159.89,159.03,143.99,133.96,132.35,129.35,128.65,127.73,125.65,111.99,90.97,55.47,55.07,40.12,31.73；
HRMS(ESI):calculated for C23H23ClO3SeK[M+K]+＝501.0127,found 501.0133。
实施例29
与实施例1不同的是，本实施例采用双(4-溴苯基)硒醚代替实施例1中的二苯基二硒醚烯，得到黄色粘稠状液体(2-苯基-2-(2,4,6-三甲氧基苯基)乙基)(对溴苯基)硒烷，产率为82％，该产物的结构表征数据如下所示：
1H NMR(400MHz,CDCl3)δ＝7.36–7.22(m,8H),7.15(dd,J＝8.1,6.4,1H),6.11(d,J＝6.1,2H),4.94(ddd,J＝16.6,9.7,7.0,1H),3.94–3.85(m,1H),3.84–3.78(m,3H),3.78–3.67(m,7H)；
13C NMR(75MHz,Chloroform-d)δ＝159.88,159.02,143.96,134.16,131.73,131.56,130.09,127.73,125.65,120.35,111.95,90.94,55.48,55.08,40.09,31.61；
HRMS(ESI):calculated for C23H24BrO3Se[M+H]+＝507.0072,found 507.0069。
实施例30
与实施例1不同的是，本实施例采用双(2-氯苯基)硒醚代替实施例1中的二苯基二硒醚烯，得到黄色粘稠状液体(2-苯基-2-(2,4,6-三甲氧基苯基)乙基)(邻氯苯基)硒烷，产率为78％，该产物的结构表征数据如下所示：
1H NMR(400MHz,CDCl3)δ＝7.43–7.12(m,9H),6.13(s,2H),5.01(dt,J＝15.8,7.9,1H),3.94(ddd,J＝11.0,9.4,5.4,1H),3.84–3.72(m,10H)；
13C NMR(75MHz,Chloroform-d)δ＝159.95,159.11,144.02,133.68(d,J＝197.2),131.08,129.16,127.79,127.41,126.84,126.71,125.72,112.07,91.09,55.58,55.14,39.59,29.99；
HRMS(ESI):calculated for C23H23ClNaO3Se[M+Na]+＝485.0390,found485.0394。
实施例31
与实施例1不同的是，本实施例采用双(3-甲苯基)硒醚代替实施例1中的二苯基二硒醚烯，得到黄色粘稠状液体(2-苯基-2-(2,4,6-三甲氧基苯基)乙基)(间甲苯基)硒烷，产率为71％，该产物的结构表征数据如下所示：
1H NMR(400MHz,CDCl3)δ＝7.35(t,J＝6.3,2H),7.30–7.22(m,4H),7.18–7.10(m,2H),7.03(d,J＝7.5,1H),6.12(d,J＝5.6,2H),4.97(dt,J＝18.4,9.2,1H),3.94–3.89(m,1H),3.81(d,J＝5.3,3H),3.77–3.71(m,7H),2.34(d,J＝7.9,3H)；
13C NMR(75MHz,Chloroform-d)δ＝159.80,159.10,144.23,138.25,133.16,131.05,129.49,128.42,127.80,127.68,127.11,125.56,112.32,91.01,55.52,55.06,40.23,31.36,21.17；
HRMS(ESI):calculated for C24H27O3Se[M+H]+＝443.1106,found 443.1120。
实施例32
与实施例1不同的是，本实施例采用吲哚代替实施例1中的1,3,5-三甲氧基苯，得到黄色粘稠状液体3-(1-苯基-2-(苯基硒基)乙基)-1H-吲哚，产率为81％，该产物的结构表征数据如下所示：
1H NMR(400MHz,Chloroform-d)δ＝7.96(s,1H),7.65–7.57(m,2H),7.50(dd,J＝8.0,1.1,1H),7.46–7.25(m,10H),7.15(ddd,J＝8.0,6.9,1.1,1H),7.06(d,J＝2.4,1H),4.69(t,J＝7.8,1H),3.87(dd,J＝11.7,7.5,1H),3.65(dd,J＝11.8,8.1,1H)；
13C NMR(101MHz,Chloroform-d)δ＝143.91,136.56,132.82,131.27,129.22,128.62,128.03,126.98,126.81,126.79,122.29,121.74,119.58,119.39,118.86,111.38,43.68,34.46；
HRMS(ESI):calculated for C22H19NSeNa[M+Na]+＝400.0575,found 400.0577。
需要说明的是，上述部分实施例产物产率较低是由于实施例2-实施例32所采用的反应时间与实施例1相同，均为12h，不同的苯乙烯和/或苯乙烯衍生物、富电子芳烃、以及二硒醚原料进行三组分反应，反应完全所需的时间是不同的，在实际应用时，可如实施1一样通过TLC检查反应进展，确认反应完成，提高产物产率。
需要说明的是，除了上述实施例中采用的反应温度外，本发明在25-80℃之间的温度条件下，例如25℃、40℃、60℃等，也成功制备得到了芳基硒醚类化合物，且产物的产率随着温度的升高而升高。需要说明的是，除了上述实施例中采用的有机溶剂外，本发明采用其他如乙酸乙酯、二氯甲烷、甲苯等有机溶剂，也成功制备得到了芳基硒醚类化合物，在这些实施例中，根据有机溶剂的不同，采用的反应温度也不同，具体根据选用的有机溶剂的沸点进行选择；另外，本发明上述实施例中采用的乙腈有机溶剂产率更高。需要说明的是，除了上述实施例中采用的催化剂外，本发明也可采用其他如路易斯酸、碘单质等催化剂，不过这些催化剂的产率没有上述实施例中采用氯化铁催化剂的产率高。需要说明的是，除了上述实施例中采用的淬灭、萃取、干燥、真空过滤浓缩、干燥、洗脱方法外，本发明也可采用其他现有技术方案进行处理。
综上所述，本发明可一步制得芳基硒醚类化合物，且制备过程中采用的催化剂具有稳定、丰度、低毒性、经济和生态优势的特点，绿色环保；最终获得的产物收率良好，部分能达到90％以上，与现有技术相比，具有显著的进步。
以上所述，仅是本发明的较佳实施例而已，并非对本发明作任何形式上的限制，虽然本发明已以较佳实施例揭露如上，然而并非用以限定本发明，任何熟悉本专业的技术人员，在不脱离本发明技术方案范围内，当可利用上述揭示的技术内容作出些许更动或修饰为等同变化的等效实施例，但凡是未脱离本发明技术方案的内容，依据本发明的技术实质对以上实施例所作的任何简单修改、等同变化与修饰，均仍属于本发明技术方案的范围内。
Claims (10)
1.一种芳基硒醚类化合物的合成方法，其特征在于，包括以下步骤：
将苯乙烯和/或苯乙烯衍生物、富电子芳烃、以及二硒醚溶解在有机溶剂中，混合均匀；
加入催化剂，在小于所述有机溶剂的沸点温度条件下进行反应，反应完成获得所述芳基硒醚类化合物。
2.根据权利要求1所述的芳基硒醚类化合物的合成方法，其特征在于，所述苯乙烯衍生物为4-甲基苯乙烯、4-叔丁基苯乙烯、4-苯基苯乙烯、4-三氟甲基苯乙烯、4-氟苯乙烯、4-氯苯乙烯、4-溴苯乙烯中的任意一种或多种。
3.根据权利要求1所述的芳基硒醚类化合物的合成方法，其特征在于，所述富电子芳烃为1,3,5-三甲氧基苯、1,2,4-三甲氧基苯、间甲氧基苯、邻甲氧基苯、3,5-二甲基苯甲醚、3,4,5-三甲氧基甲苯、3,4,5-三甲氧基苯酚、吲哚中的任意一种或多种。
4.根据权利要求1所述的芳基硒醚类化合物的合成方法，其特征在于，所述二硒醚为二苯基二硒醚、双(4-甲苯基)硒醚、双(4-甲氧苯基)硒醚、双(4-三氟甲苯基)硒醚、双(4-氟苯基)硒醚、双(4-氯苯基)硒醚、双(4-溴苯基)硒醚、双(2-氯苯基)硒醚、双(3-甲苯基)硒醚中的任意一种或多种。
5.根据权利要求1所述的芳基硒醚类化合物的合成方法，其特征在于，所述有机溶剂为乙腈。
6.根据权利要求1所述的芳基硒醚类化合物的合成方法，其特征在于，所述催化剂为氯化铁。
7.根据权利要求1所述的芳基硒醚类化合物的合成方法，其特征在于，所述反应的时间为12h。
8.根据权利要求1-7中任意一项所述的芳基硒醚类化合物的合成方法，其特征在于，还包括利用薄板层析检测反应是否完成的步骤。
9.根据权利要求8所述的芳基硒醚类化合物的合成方法，其特征在于，反应完成后还包括以下步骤：待反应混合物冷却至室温，加入饱和氯化钠溶液淬灭所述反应混合物；然后用乙酸乙酯萃取所述反应混合物，接着对所述反应混合物进行干燥、真空过滤浓缩；得到的残渣利用硅胶闪色谱纯化，最后用石油醚或乙酸乙酯洗脱得到所述芳基硒醚类化合物。
10.一种芳基硒醚类化合物，其特征在于，采用权利要求1-9中任意一项所述的芳基硒醚类化合物的合成方法制备而成。
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