CN101058554A - Chemical synthesis method for substituting alpha, beta unsaturated ketone by sulphonyl - Google Patents
Chemical synthesis method for substituting alpha, beta unsaturated ketone by sulphonyl Download PDFInfo
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- CN101058554A CN101058554A CN 200710069009 CN200710069009A CN101058554A CN 101058554 A CN101058554 A CN 101058554A CN 200710069009 CN200710069009 CN 200710069009 CN 200710069009 A CN200710069009 A CN 200710069009A CN 101058554 A CN101058554 A CN 101058554A
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Abstract
The invention discloses a chemical synthesizing method of alpha, beta-unsaturated ketone substituted by sulfonyl as formula (I), which comprises the following steps: adding unsaturated ketone as formula (III) and 2,4,4,6-tetrabromine-2, 5-cyclohexadiene-1-ketone as bromide agent as formula (II); disposing to obtain the rough product of bromide; proceeding nucleophilic reaction for rough bromide product and RSO2Na as formula (IV); making R and R1 in the formula (I) as alkyl or aryl with random carbon number; setting the molar rate of unsaturated ketone and bromide agent at 1:1-2; setting the bulk rate of each molar of unsaturated ketone and aprotic polar solvent at 1:5-50; obtaining the density of inorganic acid in the aprotic solvent at 0. 1%-5%(g/ml).
Description
(1) technical field
The present invention relates to a kind of alkylsulfonyl and replace α, the chemical synthesis process of beta unsaturated ketone.
(2) background technology
Alkylsulfonyl replaces α; beta unsaturated ketone is the prochiral double coordination type of a class reaction substrate in the Diels-Alder reaction; in the asymmetry catalysis Diels-Alder of our research reaction, can be used as dienophile; in Hetero Diels-Alder reaction, can be used as the diene body; in the Michael reaction; both can be used as receptor, can be used as donor again.Prove in the result of study of having reported, in above-mentioned reaction, can effectively mate with chiral catalyst as a kind of novel reaction substrate, reach the three-dimensional control of ideal effect, the chipal compounds that has synthesized high enantioselectivity is having broad application prospects aspect synthesis of chiral medicine and the natural goods.
Replace α for alkylsulfonyl, beta unsaturated ketone synthetic reported two kinds of methods.A kind of method is at-78 ℃, and under the effect of butyllithium reagent, the alkylsulfonyl of generation replaces acetone negative ion and aldehyde compound reaction, and dehydration makes target product again.
But this method needs to carry out under the low temperature, and condition is harsh, is difficult to synthesize the more difficult suitability for industrialized production of carrying out under general laboratory condition.Another kind method is is raw material to replace aromatic aldehyde and acetone, carry out condensation reaction under the alkali effect gets condensation product, with brominated reagent Ph
3P
+CH
2CH
2COOHBr
3 -After the reaction, carry out nucleophilic reaction with benzene sulfinic acid sodium salt again and obtain target product.Though second method has overcome the some shortcomings of first method, can only be used for the synthetic of aromatics product, its limitation is still arranged.
Replace α, the chemical synthesis process of beta unsaturated ketone so be necessary to design a kind of alkylsulfonyl simple to operate, that be convenient to suitability for industrialized production.
(3) summary of the invention
Alkylsulfonyl replaces α in the prior art in order to solve, and the synthetic limitation of beta unsaturated ketone helps suitability for industrialized production.The invention provides a kind of simple to operately, the alkylsulfonyl of being convenient to suitability for industrialized production replaces α, the chemical synthesis process of beta unsaturated ketone.
The present invention for the technical scheme that solution prior art problem is adopted is:
Alkylsulfonyl shown in a kind of formula (I) replaces α; the chemical synthesis process of beta unsaturated ketone; it is characterized in that described method carries out as follows: in being dissolved with the aprotic polar solvent of mineral acid; adding is suc as formula the brominated reagent 2,4,4 shown in beta-unsaturated ketone shown in (III) and the formula (II); the 6-tetrabromobisphenol; 5-cyclohexadiene-1-ketone carries out bromo-reaction, and the bromo-reaction product gets the bromo-derivative crude product through aftertreatment, the RSO shown in bromo-derivative crude product and the formula (IV)
2Na carries out nucleophilic reaction, and nucleophilic reaction product recrystallization obtains described alkylsulfonyl and replaces α, beta unsaturated ketone compound, R in the formula (I), R
1Respectively the do for oneself alkyl or aryl of any carbon number; The molar feed ratio of described beta-unsaturated ketone and brominated reagent is 1: 1～2; The usage quantity of described aprotic polar solvent is every mole of beta-unsaturated ketone and the volume ratio of aprotic polar solvent is 1: 5～50; The concentration of mineral acid is 0.1%～5% (g/ml) in the described aprotic polar solvent that is dissolved with mineral acid.Here the concentration of said mineral acid is meant the concentration that earlier mineral acid is dissolved in the aprotic polar solvent, in every g/ml.
(IV)
Concrete reaction formula is as follows:
Described aprotic polar solvent is 1, and 4-dioxane, acetonitrile, tetrahydrofuran (THF), DMF or DMSO are preferably 1, the 4-dioxane.
Described mineral acid is a protonic acid, as spirit of salt, Hydrogen bromide etc., is preferably spirit of salt.
Described beta-unsaturated ketone and brominated reagent 2,4,4, the 6-tetrabromobisphenol, the molar feed ratio of 5-cyclohexadiene-1-ketone is 1: 1～2; The usage quantity of described aprotic polar solvent is every mole of beta-unsaturated ketone and the volume ratio of aprotic polar solvent is 1: 5～50; The concentration of mineral acid is 0.1%～5% (g/ml) in the described aprotic polar solvent that is dissolved with mineral acid.
Described beta-unsaturated ketone and brominated reagent 2,4,4, the 6-tetrabromobisphenol, the molar feed ratio of 5-cyclohexadiene-1-ketone is preferably 1: 1; The usage quantity of described aprotic polar solvent is every mole of beta-unsaturated ketone and the volume ratio of aprotic polar solvent is preferably 1: 15; The concentration of the concentration mineral acid of mineral acid is preferably 1% (g/ml) in the described aprotic polar solvent that is dissolved with mineral acid.
Nucleophilic reaction of the present invention be with the bromo-derivative crude product with dissolve with ethanol after with the RSO shown in the formula (IV)
2Na reacts.Described alcoholic acid dosage is enough to dissolve the bromo-derivative crude product and gets final product.
The described bromo-reaction time is 1～5 hour; Described bromo-reaction temperature is 10～100 ℃.
The described bromo-reaction time is preferably 2 hours; Described bromo-reaction temperature is preferably 20 ℃.
Described bromo-reaction product postprocessing is for using saturated NaHCO
3Neutralization, CH
2Cl
2Extraction is dry, concentrate the bromination product crude product.
Described recrystallization gets the alkylsulfonyl shown in the formula (I) and replaces α, beta unsaturated ketone compound for using ethyl alcohol recrystallization.
Concrete, described method recommends to carry out as follows:
Be dissolved with 1 of spirit of salt, in the 4-dioxane, suc as formula the brominated reagent 2 shown in beta-unsaturated ketone shown in (III) and the formula (II), 4,4, the 6-tetrabromobisphenol, 5-cyclohexadiene-1-ketone carried out bromo-reaction 2 hours under 20 ℃ of conditions, the saturated NaHCO of gained bromo-reaction product
3Neutralization, CH
2Cl
2Extraction is dry, concentrate the bromo-derivative crude product, the bromo-derivative crude product in alcohol solvent with the RSO shown in the formula (IV)
2Na carries out nucleophilic reaction, and the nucleophilic reaction product is used ethyl alcohol recrystallization again, obtains described alkylsulfonyl and replaces α, beta unsaturated ketone, R in the formula (I), R
1The alkyl or aryl of respectively doing for oneself; The molar feed ratio of described beta-unsaturated ketone and brominated reagent is 1: 1; Described 1, the usage quantity of 4-dioxane is every mole of beta-unsaturated ketone and 1, and the volume ratio of 4-dioxane is 1: 15; Described 1 of the spirit of salt that is dissolved with, the concentration of spirit of salt is 1% (g/ml) in the 4-dioxane.
Alkylsulfonyl of the present invention replaces α, and the beneficial effect of the chemical synthesis process of beta unsaturated ketone is mainly reflected in: (1) is simple to operate, is beneficial to control, is convenient to suitability for industrialized production; (2) raw material cheaply is easy to get, and has reduced cost; (3) the technology three wastes discharge amount is few, compliance with environmental protection requirements, and environmental pollution is little.
(4) embodiment
The present invention is described further below in conjunction with specific embodiment:
Embodiment 1:4-phenyl-1-benzenesulfonyl-3-fourth is rare-preparation of 2-ketone
In the 500ml there-necked flask of mechanical stirring device is housed, add 4-phenyl-3-butene-2-ketone 1.0g (6.8mmol), 2,4,4, the 6-tetrabromobisphenol, 5-cyclohexadiene-1-ketone 2.8g (6.8mmol), and then adding 100ml is dissolved with 1 of 1% (g/ml) HCl, 4-dioxane, stirring at room 2 hours.Stopped reaction, saturated NaHCO
3Neutralization, CH
2Cl
2Extraction is dry, concentrates, and is dissolved in the 100ml ethanol, and with the reaction of benzene sulfinic acid sodium salt dihydrate, aftertreatment, ethyl alcohol recrystallization gets product 1.15g, yield 65%, m.p.96-98 ℃.
1H-NMR(CDCl
3)：δ7.86-7.90(m，2H)，7.42-7.67(m，9H)，6.94(1H，d，J＝15.8Hz)，4.40(s，2H)；MS(70ev)m/z：286(M
+，7)。
Embodiment 2:4-p-methoxyphenyl-1-benzenesulfonyl-3-butene-2-ketone
In the 500ml there-necked flask of mechanical stirring device is housed, add 4-p-methoxyphenyl-3-butene-2-ketone 1.2g (6.8mmol), 2,4,4,6-tetrabromobisphenol, 5-cyclohexadiene-1-ketone 5.6g (13.6mmol), and then add the acetonitrile that 100ml is dissolved with 5% (g/ml) HCl, 60 ℃ were stirred 5 hours.Stopped reaction, saturated NaHCO
3Neutralization, CH
2Cl
2Extraction is dry, concentrates, and is dissolved in the 100ml ethanol, and with the reaction of benzene sulfinic acid sodium salt dihydrate, aftertreatment, ethyl alcohol recrystallization gets product 1.7g, yield 78%, m.p.142-144 ℃.
1H-NMR(CDCl
3)：δ7.90-7.92(m，2H)，7.52-7.67(m，6H)，6.92-6.94(d，J＝8.8Hz，2H)，6.79-6.83(d，J＝15.7Hz，1H)，4.37(s，2H)，3.86(s，3H)；MS(70ev)m/z(rel.intensity，％)316(M
+，24)。
Embodiment 3:4-(4 '-N, N-dimethylamino) phenyl-1-benzenesulfonyl-3-butene-2-ketone
In the 500ml there-necked flask of mechanical stirring device is housed, add 4-to dimethylaminophenyl-3-butene-2-ketone 1.3g (6.8mmol), 2,4,4, the 6-tetrabromobisphenol, 5-cyclohexadiene-1-ketone 2.8g (6.8mmol), and then add 100ml and be dissolved with 1 of 0.1% (g/ml) HBr, the 4-dioxane, 100 ℃ were stirred 1 hour.Stopped reaction, saturated NaHCO
3Neutralization, CH
2Cl
2Extraction is dry, concentrates, and is dissolved in the 100ml ethanol, and with the reaction of benzene sulfinic acid sodium salt dihydrate, aftertreatment, ethyl alcohol recrystallization gets product 1.0g, yield 54%, m.p.157-159 ℃.
1H-NMR(CDCl
3)：δ7.92-7.90(m，2H)，7.44-7.65(m，6H)，6.69-6.67(m，3H)，4.35(s，2H)，3.06(s，3H)。
The preparation of embodiment 4:4-naphthyl-1-benzenesulfonyl-3-butene-2-ketone
In the 500ml there-necked flask of mechanical stirring device is housed, add 4-naphthyl-3-butene-2-ketone 1.3g (6.8mmol), 2,4,4, the 6-tetrabromobisphenol, 5-cyclohexadiene-1-ketone 2.8g (6.8mmol), and then adding 100ml is dissolved with 1 of 1%HCl (g/ml), 4-dioxane, stirring at room 2 hours.Stopped reaction, saturated NaHCO
3Neutralization, CH
2Cl
2Extraction is dry, concentrates, and is dissolved in the 100ml ethanol, and with the reaction of benzene sulfinic acid sodium salt dihydrate, aftertreatment, ethyl alcohol recrystallization gets product 2.2g, yield 67%.MS(70ev)m/z：322(M
+，16)。MS(70ev)m/z：386(M
+，13)。
The preparation of embodiment 5:4-anthryl-1-benzenesulfonyl-3-butene-2-ketone
In the 500ml there-necked flask of mechanical stirring device is housed, add 4-anthryl-3-butene-2-ketone 1.7g (6.8mmol), 2,4,4, the 6-tetrabromobisphenol, 5-cyclohexadiene-1-ketone 2.8g (6.8mmol), and then adding 100ml is dissolved with 1 of 1% (g/ml) HCl, 4-dioxane, stirring at room 2 hours.Stopped reaction, saturated NaHCO
3Neutralization, CH
2Cl
2Extraction is dry, concentrates, and is dissolved in the 100ml ethanol, and with the reaction of benzene sulfinic acid sodium salt dihydrate, aftertreatment, ethyl alcohol recrystallization gets product 16.5g, yield 63%.MS(70ev)m/z：386(M
+，13)。
The preparation of embodiment 6:1-benzenesulfonyl-3-amylene-2-ketone
In the 500ml there-necked flask of mechanical stirring device is housed, add 3-amylene-2-ketone 0.6g (6.8mmol), 2,4,4,6-tetrabromobisphenol, 5-cyclohexadiene-1-ketone 2.8g (6.8mmol), and then adding 100ml is dissolved with 1 of 1% (g/ml) HCl, 4-dioxane, stirring at room 2 hours.Stopped reaction, saturated NaHCO
3Neutralization, CH
2Cl
2Extraction is dry, concentrates, and is dissolved in the 100ml ethanol, and with the reaction of benzene sulfinic acid sodium salt dihydrate, aftertreatment, ethyl alcohol recrystallization gets product 1.1g, yield 73%, m.p.73-75 ℃.
1H-NMR(CDCl
3)：δ1.95(dd，J＝7.0，1.5Hz，3H)，4.25(s，2H)，6.31(dq，J＝15.8，1.5Hz，1H)，6.97(dq，J＝15.8，7.0Hz，1H)，7.54-7.71(m，3H)，7.87-7.90(m，2H)；MS(70ev)m/z：224(M
+，8)。
The preparation of embodiment 7:1-methyl sulphonyl-3-amylene-2-ketone
In the 500ml there-necked flask of mechanical stirring device is housed, add 3-amylene-2-ketone 0.6g (6.8mmol),, 2,4,4,6-tetrabromobisphenol, 5-cyclohexadiene-1-ketone 2.8g (6.8mmol), and then adding 100ml is dissolved with 1 of 1% (g/ml) HCl, 4-dioxane, stirring at room 2 hours.Stopped reaction, saturated NaHCO
3Neutralization, CH
2Cl
2Extraction is dry, concentrates, and is dissolved in the 100ml ethanol, and with the reaction of methyl-sulfinic acid sodium dihydrate, aftertreatment, ethyl alcohol recrystallization gets product 0.8g, yield 73%, m.p.59-60 ℃.
1H-NMR(CDCl
3)：δ1.95(dd，J＝7.0，1.5Hz，3H)，3.06(s，3H)，4.17(s，2H)，6.28(dq，J＝15.8，7.0Hz，1H)，7.12(dq，J＝15.8，1.5Hz，1H)；MS(70ev)m/z：162(M
+，10)。
Embodiment 8:
The preparation of 4-(4 '-hydroxyl) phenyl-1-benzenesulfonyl-3-butene-2-ketone
In the 500mL there-necked flask of mechanical stirring device is housed, add 4-(4 '-hydroxyl) phenyl-3-butene-2-ketone 1.1g (6.8mmol), 2,4,4, the 6-tetrabromobisphenol, 5-cyclohexadiene-1-ketone 2.8g (6.8mmol), and then adding 90mL is dissolved with 1 of 1% (g/ml) HCl, 4-dioxane, stirring at room 2 hours.Stopped reaction, saturated NaHCO
3Neutralization, CH
2Cl
2Extraction is dry, concentrates, and is dissolved in the 100mL ethanol, adds the reaction of 1.09g (5.5mmol) benzene sulfinic acid sodium salt dihydrate.Aftertreatment, ethyl alcohol recrystallization gets product 0.98 gram, yield 61%, m.p.162-164 ℃.
MS(70ev)m/z(rel.intensity，％)302(M
+，15.5)，161(10.4)，147(base?peak)，91(16.7)，77(41.8)，51(23.7).Anal.Calcd.for?C
16H
14O
4S：C，63.58；H，4.64.Found：C，64.01；H，4.55。
Claims (10)
1. the alkylsulfonyl shown in the formula (I) replaces α; the chemical synthesis process of beta unsaturated ketone; it is characterized in that described method carries out as follows: in being dissolved with the aprotic polar solvent of mineral acid; adding is suc as formula the brominated reagent 2,4,4 shown in beta-unsaturated ketone shown in (III) and the formula (II); the 6-tetrabromobisphenol; 5-cyclohexadiene-1-ketone carries out bromo-reaction, and the bromo-reaction product gets the bromo-derivative crude product through aftertreatment, the RSO shown in bromo-derivative crude product and the formula (IV)
2Na carries out nucleophilic reaction, and nucleophilic reaction product recrystallization obtains described alkylsulfonyl and replaces α, beta unsaturated ketone compound, R in the formula (I), R
1Respectively the do for oneself alkyl or aryl of any carbon number; The molar feed ratio of described beta-unsaturated ketone and brominated reagent is 1: 1～2; The usage quantity of described aprotic polar solvent is every mole of beta-unsaturated ketone and the volume ratio of aprotic polar solvent is 1: 5～50, and the concentration of mineral acid is 0.1%～5% (g/ml) in the described aprotic polar solvent that is dissolved with mineral acid,
2. a kind of according to claim 1 alkylsulfonyl replaces α, and the chemical synthesis process of beta unsaturated ketone is characterized in that described aprotic polar solvent is 1,4-dioxane, acetonitrile, tetrahydrofuran (THF), DMF or DMSO; Described mineral acid is a protonic acid.
3. replace α as a kind of alkylsulfonyl as described in the claim 2, the chemical synthesis process of beta unsaturated ketone is characterized in that described aprotic polar solvent is 1, the 4-dioxane.
4. a kind of according to claim 1 alkylsulfonyl replaces α, and the chemical synthesis process of beta unsaturated ketone is characterized in that described beta-unsaturated ketone and brominated reagent 2,4,4, the 6-tetrabromobisphenol, and the molar feed ratio of 5-cyclohexadiene-1-ketone is 1: 1; The usage quantity of described aprotic polar solvent is every mole of beta-unsaturated ketone and the volume ratio of aprotic polar solvent is 1: 15, and the concentration of mineral acid is 1% (g/ml) in the described aprotic polar solvent that is dissolved with mineral acid.
5. replace α as a kind of alkylsulfonyl as described in the claim 4, the chemical synthesis process of beta unsaturated ketone, it is characterized in that described nucleophilic reaction be with the bromo-derivative crude product with dissolve with ethanol after with the RSO shown in the formula (IV)
2Na reacts.
6. a kind of according to claim 1 alkylsulfonyl replaces α, and the chemical synthesis process of beta unsaturated ketone is characterized in that the described bromo-reaction time is 1～5 hour; Described bromo-reaction temperature is 10～100 ℃.
7. replace α as a kind of alkylsulfonyl as described in the claim 6, the chemical synthesis process of beta unsaturated ketone is characterized in that the described bromo-reaction time is 2 hours; Described bromo-reaction temperature is 20 ℃.
8. a kind of according to claim 1 alkylsulfonyl replaces α, and the chemical synthesis process of beta unsaturated ketone is characterized in that described bromo-reaction product postprocessing is for using saturated NaHCO
3Neutralization, CH
2Cl
2Extraction is dry, concentrate the bromination product crude product.
9. a kind of according to claim 1 alkylsulfonyl replaces α, and the chemical synthesis process of beta unsaturated ketone is characterized in that described described recrystallization for to use ethyl alcohol recrystallization, promptly gets the alkylsulfonyl shown in the formula (I) and replaces α, the compound of beta unsaturated ketone.
10. the alkylsulfonyl shown in the formula as claimed in claim 1 (I) replaces α; the chemical synthesis process of beta unsaturated ketone; it is characterized in that described method carries out as follows: be dissolved with 1 of spirit of salt; in the 4-dioxane, suc as formula the brominated reagent 2,4 shown in beta-unsaturated ketone shown in (III) and the formula (II); 4; the 6-tetrabromobisphenol, 5-cyclohexadiene-1-ketone carried out bromo-reaction 2 hours under 20 ℃ of conditions, the saturated NaHCO of gained bromo-reaction product
3Neutralization, CH
2Cl
2Extraction is dry, concentrate the bromo-derivative crude product, the bromo-derivative crude product in alcohol solvent with the RSO shown in the formula (IV)
2Na carries out nucleophilic reaction, and the nucleophilic reaction product is used ethyl alcohol recrystallization again, obtains described alkylsulfonyl and replaces α, beta unsaturated ketone, R in the formula (I), R
1The alkyl or aryl of respectively doing for oneself; The molar feed ratio of described beta-unsaturated ketone and brominated reagent is 1: 1; Described 1, the usage quantity of 4-dioxane is every mole of beta-unsaturated ketone and 1, and the volume ratio of 4-dioxane is 1: 15; Described 1 of the spirit of salt that is dissolved with, the concentration of spirit of salt is 1% (g/ml) in the 4-dioxane.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102766077A (en) * | 2012-07-25 | 2012-11-07 | 内蒙古工业大学 | Novel method for preparing 1-phenyl-2-benzene sulfonyl acetophenone |
| CN102766170A (en) * | 2012-07-25 | 2012-11-07 | 内蒙古工业大学 | Novel method for synthesizing 2-benzenesulfonyl-1-ferrocenyl ethanone |
| CN104151214A (en) * | 2014-07-03 | 2014-11-19 | 浙江工业大学 | Method for synthesizing 2-sulfonyl ketone compounds |
-
2007
- 2007-05-25 CN CN 200710069009 patent/CN101058554A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102766077A (en) * | 2012-07-25 | 2012-11-07 | 内蒙古工业大学 | Novel method for preparing 1-phenyl-2-benzene sulfonyl acetophenone |
| CN102766170A (en) * | 2012-07-25 | 2012-11-07 | 内蒙古工业大学 | Novel method for synthesizing 2-benzenesulfonyl-1-ferrocenyl ethanone |
| CN102766077B (en) * | 2012-07-25 | 2014-07-09 | 内蒙古工业大学 | Novel method for preparing 1-phenyl-2-benzene sulfonyl acetophenone |
| CN102766170B (en) * | 2012-07-25 | 2015-04-08 | 内蒙古工业大学 | Novel method for synthesizing 2-benzenesulfonyl-1-ferrocenyl ethanone |
| CN104151214A (en) * | 2014-07-03 | 2014-11-19 | 浙江工业大学 | Method for synthesizing 2-sulfonyl ketone compounds |
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