CN116621745A - (2-苯氧基苯基)苯基硫醚类化合物及其合成方法 - Google Patents
(2-苯氧基苯基)苯基硫醚类化合物及其合成方法 Download PDFInfo
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- YUDPDPSBLSRFNW-UHFFFAOYSA-N 1-phenoxy-2-phenylsulfanylbenzene Chemical compound C=1C=CC=C(SC=2C=CC=CC=2)C=1OC1=CC=CC=C1 YUDPDPSBLSRFNW-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 238000001308 synthesis method Methods 0.000 title abstract description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 69
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 claims abstract description 56
- -1 3- (phenylsulfinyl) propionic acid tert-butyl ester compound Chemical class 0.000 claims abstract description 34
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- 238000001035 drying Methods 0.000 claims abstract description 23
- 239000012300 argon atmosphere Substances 0.000 claims abstract description 18
- 239000002904 solvent Substances 0.000 claims abstract description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 129
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 42
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 23
- 238000013375 chromatographic separation Methods 0.000 claims description 22
- 239000003480 eluent Substances 0.000 claims description 22
- 238000000605 extraction Methods 0.000 claims description 21
- 239000003208 petroleum Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 13
- 230000002194 synthesizing effect Effects 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 230000035484 reaction time Effects 0.000 claims 1
- 150000004832 aryl thioethers Chemical class 0.000 abstract description 6
- 229910052723 transition metal Inorganic materials 0.000 abstract description 6
- 150000003624 transition metals Chemical class 0.000 abstract description 6
- 239000003054 catalyst Substances 0.000 abstract description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 abstract description 3
- 238000004587 chromatography analysis Methods 0.000 abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 abstract description 3
- 239000011737 fluorine Substances 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 20
- 239000000741 silica gel Substances 0.000 description 20
- 229910002027 silica gel Inorganic materials 0.000 description 20
- 230000006837 decompression Effects 0.000 description 19
- 238000010828 elution Methods 0.000 description 19
- 239000000203 mixture Substances 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 229910052786 argon Inorganic materials 0.000 description 4
- BDAJBOIAMYRWFR-UHFFFAOYSA-N 1-methyl-2-(2-methylphenyl)sulfanylbenzene Chemical compound CC1=CC=CC=C1SC1=CC=CC=C1C BDAJBOIAMYRWFR-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 1
- IBUFUPHYSZZRHD-UHFFFAOYSA-N 1,3-dioxole-2,4-diol Chemical compound O1C(OC(=C1)O)O IBUFUPHYSZZRHD-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 230000000561 anti-psychotic effect Effects 0.000 description 1
- 229940124350 antibacterial drug Drugs 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- MLYYVTUWGNIJIB-BXKDBHETSA-N cefazolin Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 MLYYVTUWGNIJIB-BXKDBHETSA-N 0.000 description 1
- 229960001139 cefazolin Drugs 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000886 photobiology Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
- C07D317/64—Oxygen atoms
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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
- C07D333/26—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 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
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- Y—GENERAL 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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Abstract
本发明公开了一种(2‑苯氧基苯基)苯基硫醚类化合物及其合成方法,包括下述步骤:在氩气氛围下,将3‑(苯基亚磺酰基)丙酸叔丁酯类化合物与2‑(三甲基硅基)三氟甲磺酸苯酯类化合物置于一10 mL史莱克管中,加入氟化铯后加入溶剂乙腈,室温下反应6小时;反应结束后萃取、色谱分离、干燥即得目标产物。本发明仅使用廉价易得的氟化铯为氟源,无需过渡金属催化剂参与即可在温和条件下高效得到芳基硫醚类化合物,该方法为制备各种多种功能化芳基硫醚类化合物提供了一条新的途径。
Description
技术领域
本发明属于有机化合物合成及应用技术领域,具体涉及一种(2-苯氧基苯基)苯基硫醚类化合物及其合成方法。
背景技术
芳基硫化物是广泛存在于药物和材料中的重要结构单元(J.Nat.Prod.2007,70,439-442.;Chem.Rev.2009,109,1141-1276.;J.Med.Chem.2014,57,2832-2842.;Chem.Mater.2014,26,724-744.)。它们可被用作合成重要中间体,也可被用作有机合成中的各种手性配体。(J.Am.Chem.Soc.2003,125,3534-3543.;Chem.Rev.2007,107,5133-5209.;Angew.Chem.,Int.Ed.2016,55,2200-2204.;Org.Chem.Front.2015,2,973-977.;Angew.Chem.,Int.Ed.2015,54,8791-8794.)。目前,市场上有许多用于治疗各种疾病的含硫药物,例如抗精神病药物氯丙噻吩(Photochemistry and Photobiology,2009,85,895-900·)和抗菌药物头抱唑林(J.Org.Chem.1997,62,9099-9106)。因此,芳基硫醚类化合物的制备受到了有机工作者的广泛关注。
目前为止,已知的合成芳基硫醚化合物的方法有很多,但大多都是依赖于过渡金属催化剂催化的芳基卤化物和含硫亲核试剂之间的偶联反应。这类反应不仅需要较高温度,还需要价格昂贵的过渡金属催化剂的参与(Angew.Chem.,Int.Ed.2008,47,2880-2883.;J.Am.Chem.Soc.2008,130,12214-12215.;Chem.Commun.2012,48,76-78.)。因此,开发不含过渡金属参与的芳基硫化物的合成策略是非常有必要的。
有鉴于此,特提出本发明。
发明内容
本发明的目的是提供一种(2-苯氧基苯基)苯基硫醚类化合物及其合成方法,该方法简单易行,成本低廉且易于纯化。在本发明中,仅使用廉价易得的氟化铯为氟源,在无过渡金属催化剂的条件下开发了一种条件温和,操作简便,方法高效的芳基硫醚类化合物的合成方法,该方法为制备多种功能化芳基硫醚类化合物提供了一条新的途径。
为实现上述目的,本发明采用以下技术方案:
一种(2-苯氧基苯基)苯基硫醚类化合物,其结构通式为:
其中R1为氢、烷基、烷氧基、卤素或三氟甲基;R2为氢、烷基、烷氧基、卤素或三氟甲基。
本发明所述的(2-苯氧基苯基)苯基硫醚类化合物的合成方法,包括下述步骤:在氩气氛围下,将3-(苯基亚磺酰基)丙酸叔丁酯化合物与2-(三甲基硅基)三氟甲磺酸苯酯类化合物加入反应管中,加入氟化铯,最后加入溶剂,室温下反应6小时;反应结束后萃取,萃取完全后,将有机相旋蒸浓缩后色谱分离、干燥即得目标产物,反应方程式如下:
所述3-(苯基亚磺酰基)丙酸叔丁酯化合物的通式为:
2-(三甲基硅基)三氟甲磺酸苯酯类化合物的结构通式为:
其中R1为氢、烷基、烷氧基、卤素或三氟甲基;R2为氢、烷基、烷氧基、卤素或三氟甲基。
进一步,所述3-(苯基亚磺酰基)丙酸叔丁酯化合物与2-(三甲基硅基)三氟甲磺酸苯酯类化合物的物质的量比为1:2.2。
进一步,所述氟化铯的用量为3-(苯基亚磺酰基)丙酸叔丁酯化合物的物质的量6.6倍。
进一步,所述的溶剂乙腈,以0.1mmol 3-(苯基亚磺酰基)丙酸叔丁酯化合物的物质的量为基准,所述溶剂的用量为1mL。
进一步,所述萃取采用的萃取剂为乙酸乙酯。
进一步,所述色谱分离采用的洗脱剂为体积比为1:10的乙酸乙酯和石油醚。
本发明的有益效果:本发明为合成(2-苯氧基苯基)苯基硫醚类化合物提供了一种简便易行的方法。该方法仅使用廉价易得的氟化铯为氟源,在无过渡金属催化剂的条件下开发了一种条件温和,操作简便,方法高效的芳基硫醚类化合物的合成方法,该方法为制备多种功能化芳基硫醚类化合物提供了一条新的途径。
具体实施方式
下面结合具体实施例,对本发明做进一步说明。应理解,以下实施例仅用于说明本发明而非用于限制本发明的范围,该领域的技术熟练人员可以根据上述发明的内容做出一些非本质的改进和调整。
实施例1
本实施例的化合物(4-甲苯基)(2-苯氧基苯基)硫醚的结构式为:
制备方法为:在氩气氛围下,往10mL史莱克管中依次加入26.8mg(0.1mmol)的3-(对甲苯基亚磺酰基)丙酸叔丁酯化合物,65.6mg(0.22mmol)的2-(三甲基硅基)三氟甲磺酸苯酯,100.3mg(0.66mmol)的氟化铯,乙腈1mL,室温反应6小时;反应结束后,利用乙酸乙酯萃取,减压浓缩后色谱分离(硅胶200-300目,洗脱剂:乙酸乙酯/石油醚梯度淋洗,比例1:10),干燥得白色固体,产率94%;1H NMR(600MHz,CDCl3)δ7.44(d,J=8.3Hz,2H),7.34–7.29(m,2H),7.08(t,J=7.6Hz,2H),6.96(dd,J=13.3,7.5Hz,3H),6.89(dd,J=14.7,8.7Hz,4H),3.81(s,3H)ppm.13C NMR(151MHz,CDCl3)δ157.2,153.9,138.1,133.5,130.3,130.2,129.9,129.8,129.5,127.3,124.3,123.1,119.4,118.2,21.2ppm.
实施例2
本实施例的化合物(2-甲苯基)(2-苯氧基苯基)硫醚的结构式为:
制备方法为:在氩气氛围下,往10mL史莱克管中依次加入26.8mg(0.1mmol)的3-(邻甲苯基亚磺酰基)丙酸叔丁酯化合物,65.6mg(0.22mmol)的2-(三甲基硅基)三氟甲磺酸苯酯,100.3mg(0.66mmol)的氟化铯,乙腈1mL,室温反应6小时;反应结束后,利用乙酸乙酯萃取,减压浓缩后色谱分离(硅胶200-300目,洗脱剂:乙酸乙酯/石油醚梯度淋洗,比例1:10),干燥得黄色油状物,产率90%;1H NMR(600MHz,CDCl3)δ7.40(d,J=7.1Hz,1H),7.34–7.29(m,2H),7.25(qd,J=8.0,7.5,1.9Hz,2H),7.15-7.19(m,1H),7.12(td,J=7.7,1.7Hz,1H),7.08(t,J=7.4Hz,1H),7.00–6.95(m,3H),6.92-6.87(m,2H),2.36(s,3H)ppm.13C NMR(151MHz,CDCl3)δ158.1,154.0,141.3,134.5,131.9,130.7,129.8,129.7,128.9,128.5,127.2,126.8,124.3,123.1,119.5,118.2,20.6ppm.
实施例3
本实施例的化合物(3-甲苯基)(2-苯氧基苯基)硫醚的结构式为:
制备方法为:在氩气氛围下,往10mL史莱克管中依次加入26.8mg(0.1mmol)的3-(3-甲苯基亚磺酰基)丙酸叔丁酯化合物,65.6mg(0.22mmol)的2-(三甲基硅基)三氟甲磺酸苯酯,100.3mg(0.66mmol)的氟化铯,乙腈1mL,室温反应6小时;反应结束后,利用乙酸乙酯萃取,减压浓缩后色谱分离(硅胶200-300目,洗脱剂:乙酸乙酯/石油醚梯度淋洗,比例1:10),干燥得黄色固体,产率91%;1H NMR(600MHz,CDCl3)δ7.31(dd,J=8.6,7.3Hz,2H),7.25(d,J=2.2Hz,1H),7.21(dd,J=4.8,1.6Hz,2H),7.18–7.12(m,2H),7.11–7.05(m,2H),7.01(td,J=7.6,1.4Hz,1H),6.94(dd,J=8.7,1.2Hz,2H),6.90(dd,J=8.1,1.3Hz,1H),2.31(s,3H)ppm.13C NMR(151MHz,CDCl3)δ157.2,154.5,139.1,133.4,133.2,131.4,129.7,129.1,128.8,128.5,127.8,124.2,123.2,22.8ppm.
实施例4
本实施例的化合物(2,4-二甲基苯基)(2-苯氧基苯基)硫醚的结构式为:
制备方法为:在氩气氛围下,往10mL史莱克管中依次加入28.2mg(0.1mmol)的3-(2,4-二甲苯基亚磺酰基)丙酸叔丁酯化合物,65.6mg(0.22mmol)的2-(三甲基硅基)三氟甲磺酸苯酯,100.3mg(0.66mmol)的氟化铯,乙腈1mL,室温反应6小时;反应结束后,利用乙酸乙酯萃取,减压浓缩后色谱分离(硅胶200-300目,洗脱剂:乙酸乙酯/石油醚梯度淋洗,比例1:10),干燥得无色油状物,产率92%;1H NMR(600MHz,CDCl3)δ7.36(d,J=7.8Hz,1H),7.34–7.29(m,2H),7.11(s,1H),7.10–7.06(m,2H),7.02–6.97(m,3H),6.94(td,J=7.6,1.4Hz,1H),6.89(dd,J=8.1,1.3Hz,1H),6.76(dd,J=7.9,1.6Hz,1H),2.33(d,J=5.8Hz,6H)ppm.13C NMR(151MHz,CDCl3)δ157.3,153.3,141.9,139.1,135.6,131.7,130.1,129.7,128.5,127.7,127.6,126.5,124.3,123.0,119.5,118.0,21.1,20.5ppm.
实施例5
本实施例的化合物(2,6-二甲基苯基)(2-苯氧基苯基)硫醚的结构式为:
制备方法为:在氩气氛围下,往10mL史莱克管中依次加入28.2mg(0.1mmol)的3-(2,6-二甲基苯基亚磺酰基)丙酸叔丁酯化合物,65.6mg(0.22mmol)的2-(三甲基硅基)三氟甲磺酸苯酯,100.3mg(0.66mmol)的氟化铯,乙腈1mL,室温反应6小时;反应结束后,利用乙酸乙酯萃取,减压浓缩后色谱分离(硅胶200-300目,洗脱剂:乙酸乙酯/石油醚梯度淋洗,比例1:10),干燥得黄色油状物,产率82%;1H NMR(600MHz,CDCl3)δ7.37–7.30(m,2H),7.23(dd,J=8.4,6.5Hz,1H),7.18(d,J=7.5Hz,2H),7.09(t,J=7.4Hz,1H),7.06–6.98(m,3H),6.93–6.86(m,2H),6.47(dd,J=7.8,1.6.Hz,1H),2.41(s,6H)ppm.13C NMR(151MHz,CDCl3)δ157.5,152.7,144.3,130.4,129.6,129.4,129.3,128.5,125.9,125.5,124.5,122.9,119.7,117.9,23.2ppm.
实施例6
本实施例的化合物(4-乙基苯基)(2-苯氧基苯基)硫醚的结构式为:
制备方法为:在氩气氛围下,往10mL史莱克管中依次加入28.2mg(0.1mmol)的3-(4-乙基苯基亚磺酰基)丙酸叔丁酯化合物,65.6mg(0.22mmol)的2-(三甲基硅基)三氟甲磺酸苯酯,100.3mg(0.66mmol)的氟化铯,乙腈1mL,室温反应6小时;反应结束后,利用乙酸乙酯萃取,减压浓缩后色谱分离(硅胶200-300目,洗脱剂:乙酸乙酯/石油醚梯度淋洗,比例1:10),干燥得黄色油状物,产率90%;1H NMR(600MHz,CDCl3)δ7.37(d,J=8.1Hz,2H),7.33–7.28(m,2H),7.17(d,J=7.9Hz,2H),7.15–7.10(m,1H),7.07(dd,J=15.1,7.7Hz,2H),6.99(t,J=7.6Hz,1H),6.95(d,J=7.4Hz,2H),6.89(d,J=8.0Hz,1H),2.65(q,J=7.6Hz,2H),1.24(t,J=7.6Hz,3H)ppm.13C NMR(151MHz,CDCl3)δ157.2,154.0,144.4,133.5,130.5,129.8,129.74,129.66,128.9,127.4,124.2,123.1,119.4,118.2,28.6,15.4ppm.
实施例7
本实施例的化合物(4-叔丁基苯基)(2-苯氧基苯基)硫醚的结构式为:
制备方法为:在氩气氛围下,往10mL史莱克管中依次加入31.0mg(0.1mmol)的3-(4-叔丁基苯基亚磺酰基)丙酸叔丁酯化合物,65.6mg(0.22mmol)的2-(三甲基硅基)三氟甲磺酸苯酯,100.3mg(0.66mmol)的氟化铯,乙腈1mL,室温反应6小时;反应结束后,利用乙酸乙酯萃取,减压浓缩后色谱分离(硅胶200-300目,洗脱剂:乙酸乙酯/石油醚梯度淋洗,比例1:10),干燥得无色油状物,产率85%;1H NMR(600MHz,CDCl3)δ7.39–7.33(m,4H),7.32–7.28(m,2H),7.16–7.11(m,1H),7.11–7.05(m,2H),7.02–6.98(m,1H),6.94(dt,J=7.6,1.1Hz,2H),6.89(dd,J=8.1,1.3Hz,1H),1.31(s,9H)ppm.13C NMR(151MHz,CDCl3)δ157.2,154.2,151.2,133.0,130.7,129.7,129.6,129.57,127.5,126.4,124.2,123.1,119.4,118.2,34.6,31.3ppm.
实施例8
本实施例的化合物(4-甲氧基苯基)(2-苯氧基苯基)硫醚的结构式为:
制备方法为:在氩气氛围下,往10mL史莱克管中依次加入28.4mg(0.1mmol)的3-(4-甲氧苯基亚磺酰基)丙酸叔丁酯化合物,65.6mg(0.22mmol)的2-(三甲基硅基)三氟甲磺酸苯酯,100.3mg(0.66mmol)的氟化铯,乙腈1mL,室温反应6小时;反应结束后,利用乙酸乙酯萃取,减压浓缩后色谱分离(硅胶200-300目,洗脱剂:乙酸乙酯/石油醚梯度淋洗,比例1:10),干燥得黄色固体,产率75%;1H NMR(600MHz,CDCl3)δ7.44(d,J=9.0Hz,2H),7.35–7.27(m,2H),7.13–7.05(m,2H),7.02–6.94(m,3H),6.94–6.82(m,4H),3.81(s,3H)ppm.13C NMR(151MHz,CDCl3)δ160.1,157.2,153.1,136.3,131.2,129.7,128.9,126.7,124.3,123.1,122.6,119.3,118.1,115.1,55.4ppm.
实施例9
本实施例的化合物(4-氟苯基)(2-苯氧基苯基)硫醚的结构式为:
制备方法为:在氩气氛围下,往10mL史莱克管中依次加入27.2mg(0.1mmol)的3-(4-氟苯基亚磺酰基)丙酸叔丁酯化合物,65.6mg(0.22mmol)的2-(三甲基硅基)三氟甲磺酸苯酯,100.3mg(0.66mmol)的氟化铯,乙腈1mL,室温反应6小时;反应结束后,利用乙酸乙酯萃取,减压浓缩后色谱分离(硅胶200-300目,洗脱剂:乙酸乙酯/石油醚梯度淋洗,比例1:10),干燥得白色固体,产率87%;1H NMR(600MHz,CDCl3)δ7.45–7.39(m,2H),7.34–7.28(m,2H),7.18–7.14(m,1H),7.11–7.06(m,2H),7.06–6.99(m,3H),6.93(dd,J=8.7,1.2Hz,2H),6.90(dd,J=8.1,1.3Hz,1H)ppm.13C NMR(151MHz,CDCl3)δ163.5,161.8,157.0,154.3,135.2,135.1,130.9,129.7,129.0,128.7,127.9,124.3,123.3,119.4,118.2,116.5,116.4ppm.
实施例10
本实施例的化合物(4-氯苯基)(2-苯氧基苯基)硫醚的结构式为:
制备方法为:在氩气氛围下,往10mL史莱克管中依次加入28.8mg(0.1mmol)的3-(4-氯苯基亚磺酰基)丙酸叔丁酯化合物,65.6mg(0.22mmol)的2-(三甲基硅基)三氟甲磺酸苯酯,100.3mg(0.66mmol)的氟化铯,乙腈1mL,室温反应6小时;反应结束后,利用乙酸乙酯萃取,减压浓缩后色谱分离(硅胶200-300目,洗脱剂:乙酸乙酯/石油醚梯度淋洗,比例1:10),干燥得白色固体,产率74%;1H NMR(600MHz,CDCl3)δ7.34–7.28(m,4H),7.28–7.24(m,2H),7.21(t,J=7.5Hz,2H),7.09(t,J=7.4Hz,1H),7.05(td,J=7.6,1.3Hz,1H),6.95–6.87(m,3H)ppm.13C NMR(151MHz,CDCl3)δ156.9,155.2,133.4,133.0,132.4,129.7,129.3,128.7,127.3,124.3,123.4,119.5,118.3ppm.
实施例11
本实施例的化合物(4-溴苯基)(2-苯氧基苯基)硫醚的结构式为:
制备方法为:在氩气氛围下,往10mL史莱克管中依次加入33.2mg(0.1mmol)的3-(4-溴基亚磺酰基)丙酸叔丁酯化合物,65.6mg(0.22mmol)的2-(三甲基硅基)三氟甲磺酸苯酯,100.3mg(0.66mmol)的氟化铯,乙腈1mL,室温反应6小时;反应结束后,利用乙酸乙酯萃取,减压浓缩后色谱分离(硅胶200-300目,洗脱剂:乙酸乙酯/石油醚梯度淋洗,比例1:10),干燥得白色固体,产率74%;1H NMR(600MHz,CDCl3)δ7.41(d,J=8.4Hz,2H),7.34–7.28(m,2H),7.29-7.19(m,4H),7.09(t,J=7.4Hz,1H),7.05(td,J=7.6,1.3Hz,1H),6.94–
6.88(m,3H)ppm.13C NMR(151MHz,CDCl3)δ156.9,155.3,133.9,133.1,132.6,132.2,129.7,128.9,127.0,124.3,123.4,121.3,119.5,118.3ppm.
实施例12
本实施例的化合物(4-三氟甲基苯基)(2-苯氧基苯基)硫醚的结构式为:
制备方法为:在氩气氛围下,往10mL史莱克管中依次加入32.2mg(0.1mmol)的3-(4-三氟甲苯基亚磺酰基)丙酸叔丁酯化合物,65.6mg(0.22mmol)的2-(三甲基硅基)三氟甲磺酸苯酯,100.3mg(0.66mmol)的氟化铯,乙腈1mL,室温反应6小时;反应结束后,利用乙酸乙酯萃取,减压浓缩后色谱分离(硅胶200-300目,洗脱剂:乙酸乙酯/石油醚梯度淋洗,比例1:10),干燥得无色油状物,产率66%;1H NMR(600MHz,CDCl3)δ7.50–7.44(m,3H),7.34–7.27(m,5H),7.14–7.07(m,2H),6.95(dd,J=8.2,1.3Hz,1H),6.87(d,J=7.5Hz,2H)ppm.13C NMR(151MHz,CDCl3)δ145.3,140.6,135.2,135.0,134.8,134.6,133.8,129.5,128.2,127.9,126.48,126.46,126.43,126.41,125.8,124.0,122.2,120.4ppm.
实施例13
本实施例的化合物(2-苯氧基苯基)萘基硫醚的结构式为:
制备方法为:在氩气氛围下,往10mL史莱克管中依次加入30.4mg(0.1mmol)的3-(萘基亚磺酰基)丙酸叔丁酯化合物,65.6mg(0.22mmol)的2-(三甲基硅基)三氟甲磺酸苯酯,100.3mg(0.66mmol)的氟化铯,乙腈1mL,室温反应6小时;反应结束后,利用乙酸乙酯萃取,减压浓缩后色谱分离(硅胶200-300目,洗脱剂:乙酸乙酯/石油醚梯度淋洗,比例1:10),干燥得白色固体,产率85%;1HNMR(600MHz,CDCl3)δ7.91(s,1H),7.78(d,J=8.5Hz,1H),7.76–7.72(m,1H),7.50–7.44(m,3H),7.33–7.27(m,2H),7.19(td,J=7.3,1.5Hz,2H),7.10–7.05(m,1H),7.01(td,J=7.6,1.3Hz,1H),6.94(t,J=8.3Hz,3H)ppm.13C NMR(151MHz,CDCl3)δ157.1,154.7,133.9,132.5,131.7,131.4,131.2,129.7,129.6,128.9,128.4,128.1,127.7,127.5,126.5,126.3,124.3,123.2,119.5,118.3ppm.
实施例14
本实施例的化合物(2-苯氧基苯基)噻吩基硫醚的结构式为:
制备方法为:在氩气氛围下,往10mL史莱克管中依次加入26.0mg(0.1mmol)的3-(噻吩基亚磺酰基)丙酸叔丁酯化合物,65.6mg(0.22mmol)的2-(三甲基硅基)三氟甲磺酸苯酯,100.3mg(0.66mmol)的氟化铯,乙腈1mL,室温反应6小时;反应结束后,利用乙酸乙酯萃取,减压浓缩后色谱分离(硅胶200-300目,洗脱剂:乙酸乙酯/石油醚梯度淋洗,比例1:10),干燥得白色固体,产率70%;1H NMR(600MHz,CDCl3)δ7.50(d,J=5.4Hz,1H),7.34(t,J=7.7Hz,2H),7.30(d,J=3.6Hz,1H),7.13–7.07(m,3H),7.00(dd,J=13.3,7.6Hz,3H),6.95(d,J=7.8Hz,1H),6.86(d,J=8.1Hz,1H)ppm.13C NMR(151MHz,CDCl3)δ157.1,152.9,136.9,131.7,1310,129.8,129.6,128.10,128.05,127.0,124.4,123.3,119.0,118.3ppm.
实施例15
本实施例的化合物(2-甲氧基-6-(3-甲氧基苯氧基)苯基)甲苯基硫醚的结构式为:
制备方法为:在氩气氛围下,往10mL史莱克管中依次加入26.8mg(0.1mmol)的3-(对甲苯基亚磺酰基)丙酸叔丁酯化合物,72.2mg(0.22mmol)的6-甲氧基-2-(三甲基硅基)三氟甲磺酸苯酯,100.3mg(0.66mmol)的氟化铯,乙腈1mL,室温反应6小时;反应结束后,利用乙酸乙酯萃取,减压浓缩后色谱分离(硅胶200-300目,洗脱剂:乙酸乙酯/石油醚梯度淋洗,比例1:10),干燥得黄色油状物质,产率53%;1H NMR(600MHz,CDCl3)δ7.29(t,J=8.3Hz,1H),7.14(t,J=8.1Hz,1H),7.07(d,J=8.2Hz,2H),6.97(d,J=8.0Hz,2H),6.74(dd,J=8.4,1.1Hz,1H),6.63–6.58(m,2H),6.45–6.41(m,1H),6.39(t,J=2.4Hz,1H),3.85(s,3H),3.72(s,3H),2.25(s,3H)ppm.13C NMR(151MHz,CDCl3)δ161.5,160.8,159.0,158.4,135.2,133.7,130.6,129.9,129.3,128.2,113.5,112.4,110.7,109.0,106.8,104.6,56.4,55.3,20.9ppm.
实施例16
本实施例的化合物(2-氟-6-(3-氟苯氧基)苯基)甲苯基硫醚的结构式为:
制备方法为:在氩气氛围下,往10mL史莱克管中依次加入26.8mg(0.1mmol)的3-(3-甲苯基亚磺酰基)丙酸叔丁酯化合物,69.5mg(0.22mmol)的6-氟-2-(三甲基硅基)三氟甲磺酸苯酯,100.3mg(0.66mmol)的氟化铯,乙腈1mL,室温反应6小时;反应结束后,利用乙酸乙酯萃取,减压浓缩后色谱分离(硅胶200-300目,洗脱剂:乙酸乙酯/石油醚梯度淋洗,比例1:10),干燥得无色油状物质,产率66%;1H NMR(600MHz,CDCl3)δ7.30(td,J=8.3,6.2Hz,1H),7.25–7.19(m,1H),7.15(d,J=7.9Hz,2H),7.01(d,J=7.9Hz,2H),6.96(t,J=8.2Hz,1H),6.83–6.74(m,2H),6.63(d,J=8.3Hz,1H),6.52(d,J=10.1Hz,1H),2.27(s,3H)ppm.13CNMR(151MHz,CDCl3)δ164.6,164.3,162.9,162.6,158.34,158.26,158.99,157.97,136.6,131.8,130.6,130.53,130.47,130.4,129.8,129.6,115.82,115.80,115.2,115.0,113.73,113.71,112.0,111.8,110.3,110.2,106.0,105.8,21.0ppm.
实施例17
本实施例的化合物(2-氯-6-(3-氟苯氧基)苯基)甲苯基硫醚的结构式为:
制备方法为:在氩气氛围下,往10mL史莱克管中依次加入26.8mg(0.1mmol)的3-(3-甲苯基亚磺酰基)丙酸叔丁酯化合物,73.0mg(0.22mmol)的6-氯-2-(三甲基硅基)三氟甲磺酸苯酯,100.3mg(0.66mmol)的氟化铯,乙腈1mL,室温反应6小时;反应结束后,利用乙酸乙酯萃取,减压浓缩后色谱分离(硅胶200-300目,洗脱剂:乙酸乙酯/石油醚梯度淋洗,比例1:10),干燥得无色油状物质,产率52%;1H NMR(600MHz,CDCl3)δ7.33(d,J=8.1Hz,1H),7.27–7.24(m,1H),7.17(t,J=7.9Hz,1H),7.10(d,J=7.9Hz,2H),7.05–6.96(m,3H),6.87(d,J=8.2Hz,1H),6.68(d,J=8.4Hz,2H),2.27(s,3H)ppm.13C NMR(151MHz,CDCl3)δ158.4,157.7,140.8,136.4,135.0,132.1,130.4,130.3,129.6,129.4,126.4,126.0,123.4,118.8,118.4,116.3,21.0ppm.
实施例18
本实施例的化合物(3,4-二甲基-6-(3,4-二甲基苯氧基)苯基)甲苯基硫醚的结构式为:
制备方法为:在氩气氛围下,往10mL史莱克管中依次加入26.8mg(0.1mmol)的3-(3-甲苯基亚磺酰基)丙酸叔丁酯化合物,71.7mg(0.22mmol)的4,5-二甲基-2-(三甲基硅基)三氟甲磺酸苯酯,100.3mg(0.66mmol)的氟化铯,乙腈1mL,室温反应6小时;反应结束后,利用乙酸乙酯萃取,减压浓缩后色谱分离(硅胶200-300目,洗脱剂:乙酸乙酯/石油醚梯度淋洗,比例1:10),干燥得淡黄色油状物质,产率53%;1H NMR(600MHz,CDCl3)δ7.28–7.24(m,2H),7.09(d,J=7.9Hz,2H),7.02(d,J=8.2Hz,1H),6.99(s,1H),6.70(s,1H),6.68(d,J=2.6Hz,1H),6.63(dd,J=8.2,2.7Hz,1H),2.32(s,3H),2.20(d,J=5.9Hz,6H),2.15(d,J=7.3Hz,6H)ppm.13C NMR(151MHz,CDCl3)δ155.6,153.3,137.9,137.3,136.9,133.3,132.5,131.7,131.6,130.8,130.4,129.8,124.5,120.9,119.2,115.1,21.1,19.9,19.6,19.01,18.97ppm.
实施例19
本实施例的化合物(3,4-二氟-6-(3,4-二氟苯氧基)苯基)甲苯基硫醚的结构式为:
制备方法为:在氩气氛围下,往10mL史莱克管中依次加入26.8mg(0.1mmol)的3-(3-甲苯基亚磺酰基)丙酸叔丁酯化合物,73.5mg(0.22mmol)的4,5-二氟-2-(三甲基硅基)三氟甲磺酸苯酯,100.3mg(0.66mmol)的氟化铯,乙腈1mL,室温反应6小时;反应结束后,利用乙酸乙酯萃取,减压浓缩后色谱分离(硅胶200-300目,洗脱剂:乙酸乙酯/石油醚梯度淋洗,比例1:10),干燥得淡黄色油状物质,产率43%;1H NMR(600MHz,CDCl3)δ7.30(td,J=8.3,6.2Hz,1H),7.25–7.19(m,1H),7.15(d,J=7.9Hz,2H),7.01(d,J=7.9Hz,2H),6.96(t,J=8.2Hz,1H),6.83–6.74(m,2H),6.63(d,J=8.3Hz,1H),6.52(d,J=10.1Hz,1H),2.27(s,3H)ppm.13C NMR(151MHz,CDCl3)δ164.6,164.3,162.9,162.6,158.34,158.26,157.99,157.97,136.6,131.8,130.6,130.53,130.47,130.4,129.8,129.6,115.82,115.80,115.2,115.0,113.73,113.71,112.0,111.8,110.3,110.2,106.0,105.8,21.0ppm.
实施例20
本实施例的化合物5-苯并[1,3]二氧杂环戊醇-5-基氧基)-6-对甲苯基苯并[1,3]二氧杂环戊二醇的结构式为:
制备方法为:在氩气氛围下,往10mL史莱克管中依次加入26.8mg(0.1mmol)的3-(3-甲苯基亚磺酰基)丙酸叔丁酯化合物,75.2mg(0.22mmol)的6-(三甲基硅基)苯并[1,3]二氧杂环戊烷-5-基三氟甲烷磺酸酯,100.3mg(0.66mmol)的氟化铯,乙腈1mL,室温反应6小时;反应结束后,利用乙酸乙酯萃取,减压浓缩后色谱分离(硅胶200-300目,洗脱剂:乙酸乙酯/石油醚梯度淋洗,比例1:10),干燥得淡黄色油状物质,产率43%;1H NMR(600MHz,CDCl3)δ7.24(d,J=8.1Hz,2H),7.10(d,J=7.8Hz,2H),6.69(d,J=7.3Hz,2H),6.49(s,1H),6.45(d,J=2.4Hz,1H),6.34(dd,J=8.4,2.5Hz,1H),5.93(d,J=2.7Hz,4H),2.32(s,3H)ppm.13CNMR(151MHz,CDCl3)δ152.6,150.4,148.3,147.9,144.2,143.3,137.2,131.6,131.4,129.9,119.4,111.8,109.9,108.1,101.9,101.8,101.4,100.6,21.1ppm.
以上显示和描述了本发明的基本原理和主要特征以及本发明的优点。本行业的技术人员应该了解,本发明不受上述实施例的限制,上述实施例和说明书中描述的只是说明本发明的原理,在不脱离本发明精神和范围的前提下,本发明还会有各种变化和改进,这些变化和改进都落入要求保护的本发明范围内。本发明要求保护范围由所附的权利要求书及其等效物界定。
Claims (9)
1.一种(2-苯氧基苯基)苯基硫醚类化合物,其结构通式为:
其中R1为氢、烷基、烷氧基、卤素或三氟甲基;R2为氢、烷基、烷氧基、卤素或三氟甲基。
2.根据权利要求书1所述的(2-苯氧基苯基)苯基硫醚类化合物的合成方法,其特征在于包括下述步骤:在氩气氛围下,将3-(苯基亚磺酰基)丙酸叔丁酯类化合物与2-(三甲基硅基)三氟甲磺酸苯酯类化合物加入反应管中,加入氟化铯,最后加入溶剂进行反应;反应结束后萃取、色谱分离、干燥即得目标产物,反应方程式如下:
3.根据权利要求2所述的(2-苯氧基苯基)苯基硫醚类化合物的合成方法,其特征在于:所述3-(苯基亚磺酰基)丙酸叔丁酯类化合物的结构通式为:
所述2-(三甲基硅基)三氟甲磺酸苯酯类化合物的结构通式为:
其中R1为氢、烷基、烷氧基、卤素或三氟甲基;R2为氢、烷基、烷氧基、卤素或三氟甲基。
4.根据权利要求2所述的(2-苯氧基苯基)苯基硫醚类化合物的合成方法,其特征在于:所述反应温度为室温,反应时间为6小时。
5.根据权利要求2所述的(2-苯氧基苯基)苯基硫醚类化合物的合成方法,其特征在于:所述3-(苯基亚磺酰基)丙酸叔丁酯类化合物与2-(三甲基硅基)三氟甲磺酸苯酯类化合物的物质的量比为1:2.2。
6.根据权利要求2所述的(2-苯氧基苯基)苯基硫醚类化合物的合成方法,其特征在于:所述氟化铯与3-(苯基亚磺酰基)丙酸叔丁酯类化合物的物质的量之比为6.6:1。
7.根据权利要求2所述的(2-苯氧基苯基)苯基硫醚类化合物的合成方法,其特征在于:所述的溶剂为乙腈,以0.1mmol 3-(苯基亚磺酰基)丙酸叔丁酯类化合物为基准,所述溶剂的用量为1mL。
8.根据权利要求2所述的(2-苯氧基苯基)苯基硫醚类化合物的合成方法,其特征在于:所述萃取采用的萃取剂为乙酸乙酯。
9.根据权利要求2所述的(2-苯氧基苯基)苯基硫醚类化合物的合成方法,其特征在于:所述色谱分离采用的洗脱剂为体积比为1:10的乙酸乙酯和石油醚。
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