CN107162943A - A kind of (E) alkenyl sulfone compound and preparation method thereof - Google Patents

A kind of (E) alkenyl sulfone compound and preparation method thereof Download PDF

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CN107162943A
CN107162943A CN201710413050.6A CN201710413050A CN107162943A CN 107162943 A CN107162943 A CN 107162943A CN 201710413050 A CN201710413050 A CN 201710413050A CN 107162943 A CN107162943 A CN 107162943A
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sulfone compound
substrate
alkenyl sulfone
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张扬会
陆爱兰
潘树雷
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Tongji University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/22—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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    • C07B2200/09—Geometrical isomers

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Abstract

The present invention relates to a kind of (E) alkenyl sulfone compound and preparation method thereof, phenylSulphon hydrazine substrate, phenyl-allylene acids substrate are dissolved in organic solvent, add copper catalyst, using the oxygen in air as oxidant, reaction produces described (E) alkenyl sulfone compound, and its chemical formula isCompared with prior art, the method have the characteristics that utilizing cheap catalyst Cu2O, Green Oxidant O2, without additional additive, it is possible to obtain final required (E) alkenyl sulfone compound, and this method, for there is the substrate of different electronic effect and steric effect groups compatibility all preferable on aromatic ring, yield is higher.

Description

A kind of (E)-alkenyl sulfone compound and preparation method thereof
Technical field
The present invention relates to organic synthesis field, and in particular to a kind of (E)-alkenyl sulfone compound and preparation method thereof.
Background technology
Bioactivity of the alkenyl sulfone compound in terms of medicine has played great function, is valuable organic of a class Compound.For example, the alkene sulfone of substitution is the effective micromolecular inhibitor of many enzymes, such as HIV-1 integrases and cysteine egg White enzyme, is frequently used for pharmaceutical industry drug design process.Such compound is also the important skeleton in organic synthesis simultaneously, due to The electron-withdrawing power of sulfone allows it as Michael acceptors in alkene sulfone, can be used for cycloaddition reaction.(a)Wang G., Mahesh U.,Chen G.Y.J.,Yao S.-Q.,Organic Letters,2003,Vol.5:737~740；(b)Gordon C.P.,Griffith R.,Keller P.A.,Medicinal Chemistry,2007,Vol.3:199~220；(c)Carr R.V.C.,Paquette L.A.,Journal of the American Chemical S℃iety,1980,Vol.102: 853~855.
As the application of alkene sulfone is more and more extensive, the method that people are gradually found that some synthesis alkene sulfone compounds, but There is also such as using poisonous or unstable material, step is more and cumbersome and produces the shortcoming of a large amount of chemical wastes.More Importantly, many method regio- and stereo-selectivities are poor, what is obtained is the mixture of Z/E- type alkene sulfones.Therefore, with simple Catalyst system and catalyzing becomes very meaningful to synthesize single type alkene sulfone compound.(d)Posner G.H.,Brunelle D.J., Journal of Organic Chemistry,1972,Vol.37:3547~3549；(e)Hopkins P.B.,Fuchs P.L.,Journal of Organic Chemistry 1978,Vol.43:1208~1217；(f)Nair V.,Augustine A., Suja T.D., Synthesis, 2002,2259~2265；(g)Huang X.,Duan D.,Zheng W.,Journal of Organic Chemistry,2003,Vol.68:1958~1963；(h)Matteucci M.,Bhalay G.,Bradley M.,Organic Letters,2003,Vol.5:235~237.
The content of the invention
It is an object of the present invention to overcome the above-mentioned drawbacks of the prior art and provide one kind synthesis is simple, green Color, cheap (E)-alkenyl sulfone compound and preparation method thereof.
The purpose of the present invention can be achieved through the following technical solutions：A kind of (E)-alkenyl sulfone compound, the chemical combination The structural formula of thing is as follows：
Wherein, R1Including aryl or alkyl, R2Including aryl or alkyl.
A kind of synthetic method of (E)-alkenyl sulfone compound as described above, comprises the following steps：By phenylSulphon hydrazine Class substrate, phenyl-allylene acids substrate are dissolved in organic solvent, add copper catalyst, using the oxygen in air as oxidant, reaction Produce described (E)-alkenyl sulfone compound.
The reaction is the side of being being triggered by phenylSulphon hydrazine substrate under the oxidation of oxygen with Cu (II) first Just illustrate, phenylSulphon hydrazine substrate experienced single electron rotor process by taking benzene sulfonyl hydrazide as an example, first and obtain compoundThen deprotonation obtains compound againSubsequent compoundDischarge N2Point Son obtains sulfonyl radicalOn the other hand, phenyl-allylene acids substrate generates alkynes copper compound under Cu (II) effectsFor convenience of description, phenyl-allylene acids substrate is by taking phenylpropiolic acid as an example, and above-described sulfonyl radicalAlkynes copper compound will be then inserted intoIn so as to generating Vinyl radical And then, Vinyl radicalAlkene copper compound is obtained with Cu (I) reactionsFinally, should Alkene copper compoundGeneration protonation obtains desired product and discharges Cu (II) in the process, So as to complete whole catalytic cycle, specific course of reaction is as follows：
It is preferred that, the structural formula of the phenylSulphon hydrazine substrate is as follows：
Wherein, Ar2For aryl, it is furthermore preferred that the phenylSulphon hydrazine substrate is sulfohydrazide.
It is preferred that, the structural formula of the phenyl-allylene acids substrate is as follows：
Wherein, Ar1For aryl, it is furthermore preferred that the phenyl-allylene acids substrate is phenylpropiolic acid.
The copper catalyst includes CuCl, CuBr, Cu2O、Cu(OAc)2、Cu(NO3)2·3H2O、Cu(OTf)2、Cu (TFA)2、CuSCN、CuCl2, one kind in CuO, it is preferred that the copper catalyst is Cu2O。
It is preferred that, the organic solvent include dichloroethanes, tetrahydrofuran, DMF, dioxane or One kind in acetonitrile, it is preferred that the organic solvent is tetrahydrofuran.
It is preferred that, the mol ratio of the phenylSulphon hydrazine substrate, phenyl-allylene acids substrate and copper catalyst is (2~4)： 1：0.1.
It is preferred that, the temperature of the reaction is 70~120 DEG C, it is furthermore preferred that reaction temperature is 80 DEG C, the reaction time is 12 ~24h, it is furthermore preferred that the reaction time is 24h.
Products therefrom (E)-alkenyl sulfone compound can be separated by the method for thin-layer chromatography, column chromatography.Such as with thin Analysis, the method for column chromatography layer by layer, solvent used is the mixed solvent of non-polar solven and polar solvent.Recommendation solvent is stone Oily ether/ethyl acetate=5/1.
Compared with prior art, beneficial effects of the present invention are embodied in following several respects：
(1) cheap catalyst Cu is utilized2O, Green Oxidant O2, without additional additive, it is possible to obtain final required (E)-alkenyl sulfone compound, it is efficient and environment-friendly；
(2) preparation method of the invention is for there is the substrate of different electronic effect and steric effect groups compatibility on aromatic ring All preferably, yield is high；
(3) synthetic method is simple to operate.
Embodiment
Embodiments of the invention are elaborated below, the present embodiment is carried out lower premised on technical solution of the present invention Implement, give detailed embodiment and specific operating process, but protection scope of the present invention is not limited to following implementations Example.
Embodiment 1
The phenylpropiolic acid of transition metal copper catalysis synthesizes the reaction of alkenyl sulfone with phenylSulphon hydrazine to catalyst, solvent and anti- Research between seasonable.Wherein [Cu] is copper catalyst, and S is organic solvent, and T is reaction temperature.By the screening of reaction condition, I Drawn optimal reaction condition, THF is solvent, Cu2O is catalyst, and temperature is 80 DEG C, and the reaction time is 24h, with air In oxygen be oxidant.
WhereinaFor1H NMR yields, 18bIt is changed into N for reacting gas2Gas.
Embodiment 2
Copper catalysis phenylpropiolic acid series substrate and phenylSulphon hydrazine synthesize the reaction of alkenyl sulfone.By for phenyl-allylene acids The patulous research of substrate, this method can be applicable by finding the phenylpropiolic acid of different substituents group, and obtain medium to good receipts Rate.
Specific experiment operation is in a reaction tube for drying clean, to sequentially add phenyl-allylene acids substrate (0.02mmol), phenylSulphon hydrazine (0.04mmol) and THF (2.0mL), it is 80 DEG C to control temperature, and 24h is reacted in atmosphere.Instead After should terminating, extract after organic phase, removal of solvent under reduced pressure, target product 3 is obtained by thin-layer chromatography, is exemplified below：
Target product 3ba:(E)-1-methyl-4-(2-(phenylsulfonyl)vinyl)benzene
1H NMR(400MHz,CDCl3) δ 7.94 (d, J=8.0Hz, 2H), 7.66 (d, J=15.4Hz, 1H), 7.63- 7.51 (m, 3H), 7.38 (d, J=8.0Hz, 2H), 7.19 (d, J=8.0Hz, 2H), 6.80 (d, J=15.4Hz, 1H), 2.37 (s,3H)；13C NMR(100MHz,CDCl3)δ142.54,141.85,140.86,133.25,129.78,129.56,129.27, 128.56,127.56,125.97,21.51ppm；
HRMS(ESI-TOF)m/z:calcd for C15H14NaO2S+:281.0607(M+Na)+,found:281.0615.
Target product 3ca:(E)-1-methyl-2-(2-(phenylsulfonyl)vinyl)benzene
1H NMR(400MHz,CDCl3) δ 7.99-7.94 (m, 3H), 7.65-7.54 (m, 3H), 7.44 (d, J=7.8Hz, 1H), 7.32-7.28 (m, 1H), 7.23-7.17 (m, 2H), 6.79 (d, J=15.3Hz, 1H), 2.46 (s, 3H)；
13C NMR(100MHz,CDCl3)δ140.63,140.09,138.16,133.32,131.18,131.01, 130.91,129.30,128.08,127.61,126.81,126.44,19.74ppm；
HRMS(ESI-TOF)m/z:calcd for C15H14NaO2S+:281.0607(M+Na)+,found:281.0612.
Target product 3da:(E)-1-methyl-3-(2-(phenylsulfonyl)vinyl)benzene
1H NMR(400MHz,CDCl3) δ 7.95 (d, J=7.4Hz, 2H), 7.66 (d, J=15.4Hz, 1H), 7.64- 7.52 (m, 3H), 7.30-7.27 (m, 3H), 7.23-7.20 (m, 1H), 6.85 (d, J=15.4Hz, 1H), 2.35 (s, 3H)；
13C NMR(100MHz,CDCl3)δ142.65,140.71,138.79,133.29,132.21,132.02, 129.27,129.09,128.91,127.57,126.90,125.78,21.22ppm；
HRMS(ESI-TOF)m/z:calcd for C15H14NaO2S+:281.0607(M+Na)+,found:281.0612.
Target product 3ea:(E)-1-fluoro-4-(2-(phenylsulfonyl)vinyl)benzene
1H NMR(400MHz,CDCl3) δ 7.94 (d, J=7.2Hz, 2H), 7.67-7.48 (m, 6H), 7.08 (t, J= 8.4Hz, 2H), 6.79 (d, J=15.4Hz, 1H)；
13C NMR(100MHz,CDCl3) δ 164.31 (d, JC-F=251.5Hz), 141.12,140.55,133.42, 130.58 (d, JC-F=8.7Hz), 129.33,128.56 (d, JC-F=3.4Hz), 127.61,126.97 (d, JC-F= 2.3Hz), 116.30 (d, JC-F=22.0Hz) ppm；
HRMS(ESI-TOF)m/z:calcd for C14H11FNaO2S+:285.0356(M+Na)+,found: 285.0366.
Target product 3fa:(E)-1-methoxy-4-(2-(phenylsulfonyl)vinyl)benzene
1H NMR(400MHz,CDCl3) δ 7.94 (d, J=7.2Hz, 2H), 7.65-7.52 (m, 4H), 7.43 (d, J= 8.7Hz, 2H), 6.89 (d, J=8.7Hz, 2H), 6.71 (d, J=15.2Hz, 1H), 3.83 (s, 3H)；
13C NMR(100MHz,CDCl3)δ162.02,142.26,141.07,133.14,130.35,129.23, 127.47,124.91,124.35,114.47,55.41ppm；
HRMS(ESI-TOF)m/z:calcd for C15H14NaO3S+:297.0556(M+Na)+,found:297.0559.
Target product 3ga:(E)-1-(4-(2-(phenylsulfonyl)vinyl)phenyl)ethanone
1H NMR (400MHz, CDCl3) δ 7.97 (d, J=8.4Hz, 4H), 7.71 (d, J=15.4Hz, 1H), 7.67- 7.56 (m, 5H), 6.96 (d, J=15.4Hz, 1H), 2.61 (s, 3H)；
13C NMR(100MHz,CDCl3)δ197.10,140.73,140.14,138.64,136.54,133.67, 129.78,129.44,128.93,128.68,127.80,26.72ppm；
HRMS(ESI-TOF)m/z:calcd for C16H14NaO3S+:309.0556(M+Na)+,found:309.0571.
Embodiment 3
Copper catalysis phenylpropiolic acid and the serial substrate of phenylSulphon hydrazine synthesize the reaction of alkenyl sulfone.Pass through phenylSulphon hydrazine bottom The patulous research of thing, finds the phenylSulphon hydrazine of either electron withdraw group substitution or electron deficient substituent group, also steric hindrance The big phenylSulphon hydrazine of effect is all suitable for this method, can similarly obtain good yield.
Specific experiment operation is in a reaction tube for drying clean, to sequentially add phenylpropiolic acid (0.02mmol), phenyl Sulfohydrazide series substrate (0.04mmol) and THF (2.0mL), it is 80 DEG C to control temperature, and 24h is reacted in atmosphere.Reaction terminates Afterwards, extract after organic phase, removal of solvent under reduced pressure, target product 3 is obtained by thin-layer chromatography, is exemplified below：
Target product 3aa:(E)-1-Phenylsulfonyl-2-phenylethene
1H NMR(400MHz,CDCl3) δ 7.94 (d, J=8.4Hz, 2H), 7.69 (d, J=15.4Hz, 1H), 7.64- 7.60 (m, 1H), 7.55 (t, J=7.5Hz, 2H), 7.50-7.47 (m, 2H), 7.42-7.39 (m, 3H), 6.87 (d, J= 15.4Hz,1H)；13C NMR(100MHz,CDCl3)δ142.45,140.61,133.35,132.27,131.19,129.30, 129.04,128.53,127.60,127.17ppm；
HRMS(ESI-TOF)m/z:calcd for C14H12NaO2S+:267.0450(M+Na)+,found:267.0460.
Target product 3ab:(E)-1-Methyl-4-(2-(phenylsulfonyl)vinyl)benzene
1H NMR(400MHz,CDCl3) δ 7.83 (d, J=8.3Hz, 2H), 7.66 (d, J=15.4Hz, 1H), 7.47 (d, J =7.6Hz, 2H), 7.41-7.38 (m, 3H), 7.34 (d, J=8.0Hz, 2H), 6.85 (d, J=15.4Hz, 1H), 2.43 (s, 3H)；13C NMR(100MHz,CDCl3)δ144.38,141.92,137.66,132.40,131.09,129.95,129.04, 128.50,127.69,127.54,21.16ppm；
HRMS(ESI-TOF)m/z:calcd for C15H14NaO2S+:281.0607(M+Na)+,found:281.0613.
Target product 3ac:(E)-1-fluoro-4-(styrylsulfonyl)benzene
1H NMR(400MHz,CDCl3) δ 7.98-7.95 (m, 2H), 7.68 (d, J=15.4Hz, 1H), 7.49 (d, J= 7.9Hz, 2H), 7.44-7.38 (m, 3H), 7.25-7.20 (m, 2H), 6.84 (d, J=15.4Hz, 1H)；
13C NMR(100MHz,CDCl3) δ 165.58 (d, JC-F=254.5Hz), 142.66,136.71 (d, JC-F= 3.0Hz), 132.15,131.33,130.48 (d, JC-F=9.5Hz), 129.10,128.57,127.01,116.62 (d, JC-F =22.6Hz) ppm；
HRMS(ESI-TOF)m/z:calcd for C14H11FNaO2S+:285.0356(M+Na)+,found: 285.0365.
Target product 3ad:(E)-1-bromo-4-(styrylsulfonyl)benzene
1H NMR(400MHz,CDCl3) δ 7.81 (d, J=7.6Hz, 2H), 7.71-7.67 (m, 3H), 7.49 (d, J= 7.6Hz, 2H), 7.43-7.38 (m, 3H), 6.84 (d, J=16.0Hz, 1H)；
13C NMR(100MHz,CDCl3)δ143.07,139.68,132.61,132.08,131.40,129.17, 129.10,128.61,126.67ppm；
HRMS(ESI-TOF)m/z:calcd for C14H11BrNaO2S+:344.9555(M+Na)+,found: 344.9564.
Target product 3ae:(E)-2-(styrylsulfonyl)naphthalene
1H NMR(400MHz,CDCl3) δ 8.56 (s, 1H), 7.98 (d, J=8.2Hz, 2H), 7.93-7.87 (m, 2H), 7.75 (d, J=15.4Hz, 1H), 7.68-7.59 (m, 2H), 7.50-7.48 (m, 2H), 7.40-7.36 (m, 3H), 6.93 (d, J =15.4Hz, 1H)；
13C NMR(100MHz,CDCl3)δ142.54,137.41,135.11,132.32,132.25,131.19, 129.65,129.35,129.21,129.16,129.05,128.56,127.93,127.63,127.22,122.52ppm；
HRMS(ESI-TOF)m/z:calcd for C18H14NaO2S+:317.0607(M+Na)+,found:317.0620.
Target product 3af:(E)-1-bromo-3-(styrylsulfonyl)benzene
1H NMR(400MHz,CDCl3) δ 8.08 (s, 1H), 7.88 (d, J=7.9Hz, 1H), 7.74-7.68 (m, 2H), 7.51-7.49 (m, 2H), 7.47-7.38 (m, 4H), 6.85 (d, J=15.4Hz, 1H)；
13C NMR(100MHz,CDCl3)δ143.47,142.56,136.38,132.02,131.46,130.83, 130.48,129.10,128.66,126.45,126.16,123.23ppm；
HRMS(ESI-TOF)m/z:calcd for C14H11BrNaO2S+:344.9555(M+Na)+,found: 344.9558。

Claims (10)

1. a kind of (E)-alkenyl sulfone compound, it is characterised in that the structural formula of the compound is as follows：
Wherein, R1Including aryl or alkyl, R2Including aryl or alkyl.
2. a kind of synthetic method of (E)-alkenyl sulfone compound as claimed in claim 1, it is characterised in that including following step Suddenly：PhenylSulphon hydrazine substrate, phenyl-allylene acids substrate are dissolved in organic solvent, copper catalyst is added, with the oxygen in air Gas is oxidant, and reaction produces described (E)-alkenyl sulfone compound.
3. the synthetic method of one kind (E)-alkenyl sulfone compound according to claim 2, it is characterised in that the phenyl The structural formula of sulfonyl hydrazines substrate is as follows：
Wherein, Ar2For aryl.
4. the synthetic method of one kind (E)-alkenyl sulfone compound according to claim 3, it is characterised in that the phenyl Sulfonyl hydrazines substrate is sulfohydrazide.
5. the synthetic method of one kind (E)-alkenyl sulfone compound according to claim 2, it is characterised in that the phenylpropyl alcohol The structural formula of acetylenic acid class substrate is as follows：
Wherein, Ar1For aryl.
6. the synthetic method of one kind (E)-alkenyl sulfone compound according to claim 5, it is characterised in that the phenylpropyl alcohol Acetylenic acid class substrate is phenylpropiolic acid.
7. the synthetic method of one kind (E)-alkenyl sulfone compound according to claim 2, it is characterised in that the copper is urged Agent includes CuCl, CuBr, Cu2O、Cu(OAc)2、Cu(NO3)2·3H2O、Cu(OTf)2、Cu(TFA)2、CuSCN、CuCl2、CuO In one kind.
8. the synthetic method of one kind (E)-alkenyl sulfone compound according to claim 2, it is characterised in that described organic Solvent includes one kind in dichloroethanes, tetrahydrofuran, N,N-dimethylformamide, dioxane or acetonitrile.
9. the synthetic method of one kind (E)-alkenyl sulfone compound according to claim 2, it is characterised in that the phenyl The mol ratio of sulfonyl hydrazines substrate, phenyl-allylene acids substrate and copper catalyst is (2~4)：1：0.1.
10. the synthetic method of one kind (E)-alkenyl sulfone compound according to claim 2, it is characterised in that described anti- The temperature answered is 70~120 DEG C, and the reaction time is 12~24h.
CN201710413050.6A 2017-06-05 2017-06-05 A kind of (E) alkenyl sulfone compound and preparation method thereof Pending CN107162943A (en)

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CN116589387A (en) * 2023-04-11 2023-08-15 华南理工大学 (E) -beta-halogenated alkenyl sulfone compound and preparation method thereof

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CN108610304A (en) * 2018-06-19 2018-10-02 陕西师范大学 A kind of two fragrant and sultam class compound synthetic methods
CN108610304B (en) * 2018-06-19 2021-10-15 陕西师范大学 Synthetic method of diaryl sultam compound
CN109020848A (en) * 2018-09-28 2018-12-18 石家庄学院 (E)-alkenyl sulfone compound synthetic method
CN109020848B (en) * 2018-09-28 2020-05-26 石家庄学院 (E) Synthesis method of-alkenyl sulfone compound
CN110981676A (en) * 2019-12-23 2020-04-10 西南大学 Method for preparing β -ketosulfone compound through visible light mediated atoxic acid decarboxylation ketonization reaction
CN110981676B (en) * 2019-12-23 2022-09-30 西南大学 Method for preparing beta-ketosulfone compound through visible light mediated atoxic acid decarboxylation ketonization reaction
CN112194604A (en) * 2020-10-09 2021-01-08 绍兴文理学院 Beta-sulfuryl hydrazone derivative and preparation method and application thereof
CN112194604B (en) * 2020-10-09 2021-12-10 绍兴文理学院 Beta-sulfuryl hydrazone derivative and preparation method and application thereof
CN116589387A (en) * 2023-04-11 2023-08-15 华南理工大学 (E) -beta-halogenated alkenyl sulfone compound and preparation method thereof

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