CN113429323B - Preparation method of sulfonyl substituted styrene type axial chiral compound - Google Patents
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Abstract
The invention belongs to the technical field of organic chemistry, and particularly relates to a preparation method of sulfonyl substituted styrene axial chiral compounds. The reaction of the invention is carried out under very simple and mild conditions, and the target sulfonyl substituted styrene axial chiral compound is obtained by nucleophilic substitution reaction of 1-substituted cyclopropane alcohol, sulfur dioxide solid substitute and 1-alkynyl-2-naphthol compound under the participation of a small molecular catalyst. The method constructs a series of sulfonyl substituted styrene axial chiral compounds with high yield and high ee value; the sulfur dioxide substitutes required by the reaction are all abundant and easily-obtained chemical raw materials, so that the use of sulfonyl raw materials in the traditional yellow acylation reaction is avoided, and the method has good guiding significance and application prospect in the scientific research and industrial fields.
Description
Technical Field
The invention belongs to the technical field of organic chemistry, and particularly relates to a preparation method of sulfonyl substituted styrene axial chiral compounds.
Background
The axial chiral compound has great development potential in the fields of chiral ligands, chiral catalysts and functional materials, and therefore, the axial chiral compound is widely concerned by organic chemists. Compared with biphenyl and binaphthyl structure axial chiral frameworks, the research on the axial chirality of the styrene type is relatively less, mainly because the structure has a lower overturning energy barrier, racemization is easy to occur, and chiral control is difficult. In 2017, a subject group successfully realizes the construction of a styrene axis chiral compound by utilizing a small molecule to catalyze nucleophilic addition reaction on alkyne (nat. Commun.2017,8,15238). In addition, transition metal-catalyzed hydrocarbon functionalization (Angew. chem. int.Ed.2020,59,6576, chem. Sci.2021,12,3726.), a method for dynamic kinetic resolution (J.Am. chem. Soc.2020,142,15686) has been reported in a small amount, and it is worth noting that the Yan Syngnathus task group in 2018 successfully realizes the preparation of sulfonyl-substituted styrene axis chiral compounds by utilizing nucleophilic addition of sulfinate to a dienoquinone intermediate (J.Am. chem. Soc.2018,140, 7056). However, the reaction requires the addition of additives and the preparation of the corresponding sulfinate in advance.
Disclosure of Invention
The invention aims to provide a simple and efficient synthesis method of sulfonyl substituted styrene axial chiral compounds. According to the invention, sulfur dioxide and cyclopropanol are subjected to ring opening and in-situ preparation of sulfinic acid anions, the dienoquinone intermediate is subjected to nucleophilic attack, the synthesis of the sulfonyl substituted styrene axial chiral compound is successfully realized, no metal catalyst is required for the reaction, the conditions are mild, and the substrate applicability is wide.
The invention provides a synthesis method of sulfonyl substituted styrene axial chiral compounds, which is characterized in that 1-substituted cyclopropane alcohol, a sulfur dioxide substitute and 1-alkynyl-2-naphthol are used for efficiently constructing the sulfonyl substituted styrene axial chiral compounds in the presence of a small molecular catalyst.
Specifically, the technical scheme adopted by the invention for solving the technical problem is as follows:
a preparation method of sulfonyl substituted styrene type axial chiral compounds is characterized in that 1-substituted cyclopropane alcohol, a sulfur dioxide substitute and 1-alkynyl-2-naphthol compounds are subjected to three-component reaction in an organic solvent under the catalysis of a small molecular catalyst to obtain the sulfonyl substituted styrene type axial chiral compounds. In an organic solvent, under the catalysis of an organic small molecule catalyst, 1-substituted cyclopropane alcohol and a sulfur dioxide substitute generate negative sulfinic acid ions in situ, and generate nucleophilic substitution reaction with a dienoquinone intermediate generated in situ by the activation of the organic small molecule catalyst by 1-alkynyl-2-naphthol to obtain the sulfonyl substituted styrene type axial chiral compound.
Preferably, the reaction is of the formula:
in the formula R1Is aryl or heteroaryl; r2Is any one or more of hydrogen, electron-donating group or electron-withdrawing groupThe electron group is a halogen atom, and the electron-donating group is methoxyalkynyl; r3Is an alkyl or aryl group.
Preferably, aryl is phenyl, naphthyl, or substituted phenyl or naphthyl; the heteroaryl is an aromatic ring containing heteroatoms such as thiophene, dibenzothiophene and carbazole, the heteroaryl contains or does not contain a substituent, and the heteroatoms are common heteroatoms such as sulfur atoms, oxygen atoms and nitrogen atoms; the substituent is an electron-withdrawing group or an electron-donating group, the electron-withdrawing group is cyano, halogen, trifluoromethyl and the like, and the electron-donating group is methoxy, trifluoromethoxy methylthio, n-butyl and the like; the alkyl is a linear or cyclic alkyl of C1-C12 with or without substituent.
Preferably, the small molecule catalyst is a thiourea catalyst or a squaramide catalyst, and the molecular formula of the preferred catalyst is as follows:
preferably, the sulfur dioxide substitute is K2S2O5、Na2S2O5、NaHSO3Or DABCO (SO)2)2。
Preferably, the organic solvent is 1, 2-dichloroethane, dichloromethane, acetonitrile, toluene, trifluorotoluene, chlorobenzene, xylene or tetrahydrofuran.
Preferably, the feeding molar ratio of the 1-alkynyl-2-naphthol compound to the 1-substituted cyclopropane alcohol to the sulfur dioxide substitute to the small molecule catalyst is 1: (1-2.5): (1-3): (0.01-0.15).
Preferably, the amount of the organic solvent to be added is 10 to 20mL/mmol, more preferably, based on the 1-alkynyl-2-naphthol compound, in an amount generally used for ensuring smooth progress of the reaction.
Preferably, the reaction temperature is room temperature, the room temperature is 15-40 ℃, and the reaction time is 70-100 h; more preferably, the reaction temperature is 25 ℃ and the reaction time is 72 h.
Preferably, the reaction comprises the steps of:
(1) adding a 1-alkynyl-2-naphthol compound, 1-substituted cyclopropaneol, a sulfur dioxide substitute and a small molecular catalyst into a dry reaction tube at room temperature, adding an organic solvent under the protection of inert atmosphere, and stirring for reaction;
(2) and after the reaction is finished, carrying out post-treatment on the reaction solution to obtain the sulfonyl substituted styrene type axial chiral compound.
Preferably, the inert atmosphere is nitrogen, argon or a mixture of both.
Preferably, the post-treatment is column chromatography separation and purification, specifically, the reaction solution after the reaction is directly subjected to column chromatography separation, a mixed solvent of petroleum ether, ethyl acetate and dichloromethane is used as a mobile phase, a solution containing a target substance is collected, and the solvent is removed by concentration under reduced pressure, so that the sulfonyl-substituted styrene type axial chiral compound is obtained.
Preferably, the reaction yield is up to 87 percent, and the ee value is up to 98 percent; the structure of the compound is shown in the specification1HNMR and13the characterization by methods such as CNMR and the like is confirmed, and the ee value is detected by chiral HPLC.
Compared with the prior art, the invention has the beneficial effects that: the reaction of the invention is carried out under very simple and mild conditions, and the target product is obtained by nucleophilic substitution reaction of 1-substituted cyclopropane alcohol, sulfur dioxide solid substitute and 1-alkynyl-2-naphthol compound under the participation of small molecule catalyst. The method constructs a series of sulfonyl substituted styrene axis chiral compounds with high yield and high ee value; the sulfur dioxide substitutes required by the reaction are all abundant and easily-obtained chemical raw materials, so that the use of sulfonyl raw materials in the traditional yellow acylation reaction is avoided, and the method has good guiding significance and application prospect in the scientific research and industrial fields.
Detailed Description
The technical solution of the present invention will be further specifically described below by way of specific examples.
Example 1
To the reaction tube were added 1- (3-bromocyclobutyl) cyclopropan-1-ol (38.2mg,0.2mmol),1- (phenylethynyl) -2-naphthol (24.4mg,0.1mmol), DABCO (SO)2)2(48mg,0.2mmol) and 3- [ [3, 5-bis (trifluoromethyl) phenyl ] phenyl]Amino group]-4- [ [ (8A, 9S) -10, 11-dihydro-6' -methoxyquinuclidin-9-yl]Amino group]-3-Cyclobutane-1, 2-dione (6.3mg,0.01mmol), and after replacing it with high-purity nitrogen gas three times, trifluorotoluene (2mL) was added and the reaction was stirred at room temperature for 72 hours. After TLC monitoring reaction is finished, column chromatography separation is directly carried out, and petroleum ether: ethyl acetate: dichloromethane (4: 1: 1) was used as the mixed mobile phase to give example 1(20.9mg) as the corresponding axial chiral product in 42% yield and 93% ee.
The structural characterization of the compound of example 1,1H NMR(400MHz,CDCl3)δ8.14(s,1H),7.93(d,J＝8.9Hz,1H),7.86–7.75(m,1H),7.41–7.29(m,3H),7.24–7.17(m,1H),7.12–7.04(m,2H),7.03–6.97(m,2H),4.46–4.36(m,1H),3.55–3.42(m,1H),3.24(t,J＝7.2Hz,2H),2.92–2.70(m,4H),2.65–2.50(m,2H)；
13C NMR(100MHz,CDCl3)δ206.08,153.82,143.70,132.70,132.64,131.94,131.04,130.47,129.47,128.84,128.76,128.02,124.31,122.97,119.99,110.36,45.72,42.55,40.07,36.54,32.60.
example 2
To the reaction tube were added 1- (4-methoxyphenyl) cyclopropan-1-ol (32.8mg,0.2mmol),1- (4-methylthiophenylethynyl) -2-naphthol (29.0mg,0.1mmol), DABCO (SO)2)2(48mg,0.2mmol) and 3- [ [3, 5-bis (trifluoromethyl) phenyl ] phenyl]Amino group]-4- [ [ (8A, 9S) -10, 11-dihydro-6' -methoxyquinuclidin-9-yl]Amino group]-3-Cyclobutane-1, 2-dione (6.3mg,0.01mmol), and after replacing it with high-purity nitrogen gas three times, trifluorotoluene (2mL) was added and the reaction was stirred at room temperature for 72 hours. After TLC monitoring reaction is finished, column chromatography separation is directly carried out, and petroleum ether: ethyl acetate: dichloromethane (4: 1: 1) was used as the mixed mobile phase to obtain the corresponding axial chiral product, example 2(32.5mg), 67% yield, and 91% ee.
The structural characterization of the compound of example 2,1H NMR(400MHz,CDCl3)δ8.10(s,1H),7.90(d,J＝8.9Hz,1H),7.86–7.77(m,4H),7.41–7.32(m,2H),7.32–7.28(m,1H),6.92–6.85(m,6H),3.85(s,4H),3.47–3.34(m,4H),2.34(s,3H)；
13C NMR(100MHz,CDCl3)δ194.28,164.03,153.68,143.26,143.02,132.48,132.22,131.63,130.76,130.47,129.45,128.83,128.71,128.39,128.00,125.38,124.27,123.29,119.82,113.92,110.61,55.54,46.65,30.47,14.64.
example 3
To the reaction tube were added 1- (3-bromocyclobutyl) cyclopropan-1-ol (38.2mg,0.2mmol),1- (4-chlorophenylethynyl) -2-naphthol (27.8mg,0.1mmol), DABCO (SO)2)2(48mg,0.2mmol) and 3- [ [3, 5-bis (trifluoromethyl) phenyl ] phenyl]Amino group]-4- [ [ (8A, 9S) -10, 11-dihydro-6' -methoxyquinuclidin-9-yl]Amino group]-3-Cyclobutane-1, 2-dione (6.3mg,0.01mmol), and after replacing it with high-purity nitrogen gas three times, trifluorotoluene (2mL) was added and the reaction was stirred at room temperature for 72 hours. After TLC monitoring reaction is finished, column chromatography separation is directly carried out, and petroleum ether: ethyl acetate: dichloromethane (4: 1: 1) was used as the mixed mobile phase to give the corresponding axial chiral product, example 3(23.7mg), 50% yield, 93% ee.
The structural characterization of the compound of example 3,1H NMR(400MHz,CDCl3)δ8.11(s,1H),7.96–7.87(m,1H),7.86–7.77(m,4H),7.42–7.31(m,2H),7.29(d,J＝8.9Hz,1H),7.08–7.02(m,2H),6.97–6.85(m,4H),3.85(s,3H),3.47–3.34(m,4H)；
13C NMR(101MHz,CDCl3)δ194.29,164.10,153.66,142.18,136.94,133.95,132.70,132.08,131.48,130.67,130.49,129.43,129.05,128.76,128.09,124.38,123.15,119.74,113.95,110.13,55.54,46.66,30.42.
example 4
To the reaction tube were added 1- (p-methoxyphenyl) cyclopropan-1-ol (32.8mg,0.2mmol),1, 4-diphenylethynyl-2-naphthol (34.4mg,0.1mmol), DABCO (SO)2)2(48mg,0.2mmol) and 3- [ [3, 5-bis (trifluoromethyl) phenyl ] phenyl]Amino group]-4- [ [ (8A, 9S) -10, 11-dihydro-6' -methoxyquinuclidin-9-yl]Amino group]-3-Cyclobutane-1, 2-dione (6.3mg,0.01mmol), and after replacing it with high-purity nitrogen gas three times, trifluorotoluene (2mL) was added and the reaction was stirred at room temperature for 72 hours. After TLC monitoring reaction is finished, column chromatography separation is directly carried out, and petroleum ether: ethyl acetate: dichloromethane (4: 1: 1) was used as the mixed mobile phase to give the corresponding axial chiral product, example 4(49.6mg), 87% yield, 86% ee.
The structural characterization of the compound 4 was carried out,1H NMR(400MHz,CDCl3)δ8.16(s,1H),8.00(s,1H),7.89–7.80(m,3H),7.64(d,J＝8.7Hz,1H),7.57–7.50(m,2H),7.47(dd,J＝8.7,1.4Hz,1H),7.39–7.27(m,4H),7.21(t,J＝7.3Hz,1H),7.15–7.06(m,2H),7.06–6.98(m,2H),6.90–6.82(m,2H),3.83(s,3H),3.60–3.23(m,4H).
13C NMR(100MHz,CDCl3)δ194.37,164.11,154.43,144.07,132.89,132.35,132.07,131.86,131.62,130.99,130.53,130.36,129.07,128.79,128.40,128.32,123.61,123.23,120.45,119.03,113.97,110.79,89.86,89.30,55.54,46.82,30.52.
example 5
To the reaction tube were added 1- (4-methoxyphenyl) cyclopropan-1-ol (26.8mg,0.2mmol), 1-phenylethynyl-2-naphthol (30.1mg,0.1mmol), DABCO (SO)2)2(48mg,0.2mmol) and 1- [3, 5-bis (trifluoromethyl) phenyl) -3- { (S) [ (1S,2S,4S,5R) -5-ethyl-1-aza-bicyclo [2.2.2 ]]Oct-2-yl]- (6-methoxy-4-quinolyl) methyl } thiourea (6.0mg,0.01mmol) was substituted with high-purity nitrogen three times, and trifluorotoluene (2mL) was added thereto, followed by stirring at room temperature for 72 hours. TLC monitoring after completion of the reaction, direct columnChromatographic separation, adopting petroleum ether: ethyl acetate: dichloromethane (4: 1: 1) was used as the mixed mobile phase to give example 5(30.4mg) as the corresponding axial chiral product in 61% yield and 91% ee.
The nuclear magnetic characterization of the compound 5 was carried out,1H NMR(400MHz,CDCl3)δ8.14(s,1H),7.90(d,J＝8.9Hz,1H),7.86–7.78(m,3H),7.74(s,1H),7.66(d,J＝8.1Hz,1H),7.41–7.27(m,3H),6.95–6.84(m,6H),3.85(s,3H),3.49–3.19(m,4H),2.52–
2.31(m,2H),1.55–1.35(m,2H),1.32–1.12(m,3H),0.83(t,J＝7.3Hz,3H).
13C NMR(101MHz,CDCl3)δ194.22,164.02,153.68,146.57,143.68,132.43,132.28,131.57,130.63,130.46,129.53,129.47,128.86,128.70,127.95,124.22,123.31,119.89,113.92,110.74,55.53,46.55,35.43,32.98,30.47,22.24,13.83.
the above-described embodiments are merely preferred embodiments of the present invention, which is not intended to be limiting in any way, and other variations and modifications are possible without departing from the scope of the invention as set forth in the appended claims.
Claims (7)
1. A preparation method of sulfonyl substituted styrene type axial chiral compounds is characterized in that 1-substituted cyclopropane alcohol, sulfur dioxide substitutes and 1-alkynyl-2-naphthol compounds are subjected to three-component reaction under the catalysis of a small molecular catalyst in an organic solvent under inert atmosphere to obtain sulfonyl substituted styrene type axial chiral compounds;
wherein the reaction has the formula:
in the formula R1Is aryl or heteroaryl; r2Is any one or more of hydrogen, electron-donating group or electron-withdrawing group, the electron-withdrawing group is a halogen atom, and the electron-donating group is methoxy alkynyl; r3Is alkyl or aryl;
the sulfur dioxide substituteIs DABCO.(SO2)2；
The molecular formula of the small molecule catalyst is shown as follows:
2. the method for preparing the sulfonyl-substituted styrene type axial chiral compound according to claim 1, wherein the organic solvent is 1, 2-dichloroethane, dichloromethane, acetonitrile, toluene, trifluorotoluene, chlorobenzene, xylene or tetrahydrofuran.
3. The method for preparing sulfonyl-substituted styrene type axial chiral compounds according to claim 1, wherein the feeding molar ratio of the 1-alkynyl-2-naphthol compound, the 1-substituted cyclopropaneol, the sulfur dioxide substitute and the small molecule catalyst is 1: (1-2.5): (1-3): (0.01-0.15).
4. The method for preparing the sulfonyl-substituted styrene type axial chiral compound as claimed in claim 1, wherein the amount of the organic solvent added is 10-20mL/mmol based on the 1-alkynyl-2-naphthol compound.
5. The method for preparing the sulfonyl-substituted styrene type axial chiral compound as claimed in claim 1, wherein the reaction temperature is room temperature and the reaction time is 70-100 h.
6. The method for preparing the sulfonyl-substituted styrene type axial chiral compound according to any one of claims 1 to 5, wherein the reaction comprises the following steps:
(1) adding a 1-alkynyl-2-naphthol compound, 1-substituted cyclopropaneol, a sulfur dioxide substitute and a small molecular catalyst into a dry reaction tube at room temperature, adding an organic solvent under the protection of inert atmosphere, and stirring for reaction;
(2) and after the reaction is finished, carrying out post-treatment on the reaction solution to obtain the sulfonyl substituted styrene type axial chiral compound.
7. The method for preparing the sulfonyl-substituted styrene type axial chiral compound according to claim 6, wherein the post-treatment is directly performing column chromatography separation on the reaction solution after the reaction is finished, a mixed solvent of petroleum ether, ethyl acetate and dichloromethane is used as a mobile phase, a solution containing a target substance is collected, and the solvent is removed to obtain the sulfonyl-substituted styrene type axial chiral compound.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107473995A (en) * | 2017-07-30 | 2017-12-15 | 复旦大学 | β trifluoromethyl alkenyl sulfone compounds and its preparation method and application |
| CN111925319A (en) * | 2020-02-10 | 2020-11-13 | 台州学院 | Synthesis method of gamma-ketosulfone compound |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107473995A (en) * | 2017-07-30 | 2017-12-15 | 复旦大学 | β trifluoromethyl alkenyl sulfone compounds and its preparation method and application |
| CN111925319A (en) * | 2020-02-10 | 2020-11-13 | 台州学院 | Synthesis method of gamma-ketosulfone compound |
Non-Patent Citations (4)
| Title |
|---|
| A copper-catalyzed insertion of sulfur dioxide via radical coupling;Zhang, Jun et al;《Chemical Communications (Cambridge, United Kingdom) 》;20200213;第56卷(第21期);第3225-3228页 * |
| A metal-free reaction of sulfur dioxide, cyclopropanols and electron-deficient olefins;Zhang, Chun et al;《Chemical Communications (Cambridge, United Kingdom)》;20201015;第56卷(第89期);第13852-13855页 * |
| Organocatalytic Enantioselective Construction of Axially Chiral Sulfone-Containing Styrenes;Shiqi Jia et al;《J. Am. Chem. Soc》;20180521;第140卷;第7056-7060页 * |
| Synthesis of γ-Keto Sulfones through a Three-Component Reaction of Cyclopropanols, DABCO·(SO2)2 and Alkyl Halides;Zhang, Chun et al;《Advanced Synthesis & Catalysis》;20210405;第363卷(第12期);第3109-3114页 * |
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