CN105622478A - 3,3-dialkylthio-2-benzeneselenenyl-2-propylene-1-one derivative and synthesis thereof - Google Patents
3,3-dialkylthio-2-benzeneselenenyl-2-propylene-1-one derivative and synthesis thereof Download PDFInfo
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Abstract
The invention discloses a 3,3-dialkylthio-2-benzeneselenenyl-2-propylene-1-one derivative and a synthesis method thereof. 3,3-dialkylthio-2-propylene-1-one which is easy to prepare, has diverse structure and is used as a raw material is subjected to a substitution reaction with an organic selenium reagent under the action of an acid to synthesize the 3,3-dialkylthio-2-benzeneselenenyl-2-propylene-1-one derivative. The synthesis method has the advantages of easily obtained raw materials, simple operation, mild reaction conditions, high efficiency and the like.
Description
Technical field
The present invention relates to a kind of 3,3-bis-alkylthio group-2-phenylseleno-2-propylene-1-ketone derivatives and synthetic method thereof. It is that raw material carries out substitution reaction with organic selenium reagent under acid effect easily to prepare, to have 3,3-bis-alkylthio group-2-propylene-1-ketone of structure diversity, synthesizes 3,3-bis-alkylthio group-2-phenylseleno-2-propylene-1-ketone derivatives. The present invention has that raw material is easy to get, easy and simple to handle, reaction condition is gentle and efficiency high.
Background technology
Organic selenium compounds is important organic synthesis intermediate and food additive, or the biological template of the inhibitor of important antioxidant, enzyme, anticarcinogen and energy mimetic enzyme catalysis, has important function and purposes in organism and biochemistry. ��-phenylseleno-alpha, beta-unsaturated ketone derivant such as 3-methyl isophthalic acid-phenyl-2-phenylseleno-2-octene-1-one has been used to the research (Mol.CellBiochem.2011,355,167 172 of muroid internal organs oxidative stress parameter; FoodandChemicalToxicology2012,50,2450-2455; CellBiochem.Funct.2012,30,315 319.). 3,3-bis-alkylthio group-2-phenylseleno-2-propylene-1-ketone derivatives belong to ��-phenylseleno-��, beta-unsaturated ketone, have good application prospect in biochemistry. Additionally, 3,3-bis-alkylthio group-2-phenylseleno-2-propylene-1-ketone derivatives are owing to having by overactive double bond, functionalization can be easier to, in organic synthesis, therefore have important using value. There is bibliographical information to pass through olefine aldehydr at present and synthesize ��-phenylseleno-alpha, beta-unsaturated ketone derivant (Tetrahedron2008,64,9293-9304.) with diphenyl disenenide ether through 3 steps; Or utilize diketone to synthesize ��-phenylseleno-��, alpha, beta-unsaturated ketone derivant (TetrahedronLetters2009,50,5726-5728.) with diphenyl disenenide ether through 2 steps, but its operation is more complicated, and yield is relatively low. 3, the synthesis of 3-bis-alkylthio group-2-phenylseleno-2-propylene-1-ketone derivatives have not been reported, 3, the 3-bis-alkylthio group-2-propylene-1-ketone that the present invention utilizes easy preparation, have a structure diversity are that raw material carries out substitution reaction with organic selenium reagent, by regulating and controlling R in raw material 21And R2Substituent group, has synthesized 3,3-bis-alkylthio group-2-phenylseleno-2-propylene-1-ketone derivatives 1.
Summary of the invention
It is an object of the invention to provide a kind of raw material be easy to get, reaction condition gentleness, wide adaptability, method that 3,3-bis-alkylthio group-2-phenylseleno-2-propylene-1-ketone derivatives can be synthesized simply and easily.
To achieve these goals, technical scheme is as follows:
With acid for catalyst, 3,3-bis-alkylthio group-2-propylene-1-ketone derivatives 2 carry out substitution reaction (reaction equation 1) with organic selenium reagent in organic solvent. Reaction terminate after routinely isolation and purification method carry out product separation and sign, obtain 3,3-bis-alkylthio group-2-phenylseleno-2-propylene-1-ketone derivatives 1.
Technical scheme is characterised by:
3,3-bis-alkylthio group-2-propylene-1-ketone 2 are as synthon, and its substituent group is:
1)R1It is the alkyl of 1-4, aryl or aryl vinyl for carbon number. Wherein aryl is with the aryl of substituent group or heterocyclic aryl on phenyl, phenyl ring, and with the 1-5 kind that substituent group is in methyl, fluorine, chlorine, bromine, iodine, trifluoromethyl, nitro, cyano group, carboxyl on phenyl ring, the number of substituent group is 1-5.
2)R2For the alkyl of carbon number 1-4, pi-allyl and benzyl, orRepresent polymethylene (CH2)m. Wherein m=2,3,4.
Organic selenium reagent 3 is diphenyl disenenide ether, phenylseleno chlorine or N-phenylseleno phthalimide. Wherein, best by N-phenylseleno phthalimide effect.
Acid catalyst is sulphuric acid, p-methyl benzenesulfonic acid, trifluoromethanesulfonic acid, trifluoroacetic acid, ferric chloride or aluminum chloride. Wherein, best by Catalyzed by p-Toluenesulfonic Acid effect.
Reaction dissolvent is one or more organic solvents in methanol, ethanol, isopropanol, oxolane, 1,4-dioxane, dichloromethane, 1,2-dichloroethanes and toluene. The 3,3-bis-alkylthio group-2-propylene-1-ketone 2 mass concentration in organic solvent is 1-2%. Wherein, to carry out effect in dichloromethane or 1,2-dichloroethanes best in reaction.
The mol ratio of 3,3-bis-alkylthio group-2-propylene-1-ketone 2 and acid catalyst levels is 1:0.01-1:0.2. Wherein, optimum molar ratio is 1:0.05��1:0.1.
The mol ratio of synthon 2 and organic selenium reagent 3 is 1:1-1:5. Wherein, when mol ratio is 1:1��1:2, reaction effect is best.
Response time is 1-24 hour. Wherein, optimum reacting time is 4-6 hour.
Reaction temperature is-20-60 DEG C. Wherein, optimal reaction temperature is 0��40 DEG C.
The invention have the advantages that
1) synthon 3,3-bis-alkylthio group-2-propylene-1-ketone 2 has structure diversity, it is possible to be used for synthesizing dissimilar and structure 3,3-bis-alkylthio group-2-phenylseleno-2-propylene-1-ketone derivatives 1.
2) synthon 2 is easily prepared, and prepares raw material cheap and easily-available.
3) 3,3-bis-alkylthio group-2-phenylseleno-2-propylene-1-ketone derivatives 1 synthetic reaction condition is gentle, step is simple, product yield is high.
In a word, the present invention utilizes the structure diversity of 3,3-bis-alkylthio group-2-propylene-1-ketone 2 and organic selenium reagent to efficiently synthesize the 3 of dissimilar and structure, 3-bis-alkylthio group-2-phenylseleno-2-propylene-1-ketone derivatives 1, raw material is cheap and easily-available, easy and simple to handle, and target product yield is high.
Detailed description of the invention
Contribute to being further appreciated by the present invention by following embodiment, but present disclosure is not limited to that.
Embodiment 1
In 25mL reaction tube, it is sequentially added into p-TsOH H2O (2.9mg, 0.015mmol), 3,3-bis-alkylthio groups-2-propylene-1-ketone 2a (48.7mg, 0.30mmol), organic selenium reagent 3a (99.7mg, 0.33mmol) and 3mL solvent 1,2-dichloroethanes, 30 DEG C of reaction 5h. Reaction removes Volatile Colstituent under decompression after terminating, and then with silica gel column chromatography separation, (eluent is petroleum ether (60-90 DEG C/dichloromethane, v/v=2:1), obtains faint yellow solid target product 1a (91.4mg, yield 96%). Target product is measured by nuclear magnetic resoance spectrum and high resolution mass spectrum and is confirmed.
Embodiment 2
Reactions steps and operation are with embodiment 1, and difference from Example 1 is in that, organic selenium reagent is 3b phenylseleno chlorine (63.2mg, 0.33mmol). Stopped reaction, post-treated obtains target product 1a (47.6mg, yield 50%). Illustrate that organic selenium reagent 3b effect is effective not as organic selenium reagent 3a.
Embodiment 3
Reactions steps and operation are with embodiment 1, and difference from Example 1 is in that, reaction temperature is 0 DEG C. Stopped reaction, post-treated obtains target product 1a (87.6mg, yield 92%).
Embodiment 4
Reactions steps and operation are with embodiment 1, and difference from Example 1 is in that, reaction temperature is 40 DEG C. Stopped reaction, post-treated obtains target product 1a (91.4mg, yield 96%).
Embodiment 5
Reactions steps and operation are with embodiment 1, and difference from Example 1 is in that, reaction dissolvent is dichloromethane. Stopped reaction, post-treated does not obtain target product 1a (88.5mg, yield 93%). Illustrate that reaction effect is better in dichloromethane.
Embodiment 6
Reactions steps and operation are with embodiment 1, and difference from Example 1 is in that, reaction dissolvent is toluene. Stopped reaction, post-treated obtains target product 1a (61.9mg, yield 65%). Illustrate that toluene can also be used as reaction dissolvent, but be not optimum response solvent.
Embodiment 7
Reactions steps and operation are with embodiment 1, and difference from Example 1 is in that, reaction dissolvent is oxolane. Stopped reaction, post-treated obtains target product 1a (84.7mg, yield 89%). Illustrate that oxolane can also be used as reaction dissolvent, but be not optimum response solvent.
Embodiment 8
Reactions steps and operation are with embodiment 1, and difference from Example 1 is in that, the addition of organic selenium reagent 3a is 90.7mg (0.3mmol). Stopped reaction, post-treated obtains target product 1a (81.9mg, yield 86%).
Embodiment 9
Reactions steps and operation are with embodiment 1, and difference from Example 1 is in that, p-methyl benzenesulfonic acid consumption is 5.7mg (0.03mmol). Stopped reaction, post-treated obtains target product 1a (91.4mg, yield 96%).
Embodiment 10
Reactions steps and operation are with embodiment 1, and difference from Example 1 is in that, catalyst acid is ferric chloride 2.4mg (0.015mmol). Stopped reaction, post-treated obtains target product 1a (20.0mg, yield 21%).
Embodiment 11
Reactions steps and operation are with embodiment 1, and difference from Example 1 is in that, catalyst acid is trifluoroacetic acid 1.7mg (0.015mmol). Stopped reaction, post-treated obtains target product 1a (33.3mg, yield 35%).
Embodiment 12
Reactions steps and operation are with embodiment 1, and difference from Example 1 is in that, response time 2h. Stopped reaction, post-treated obtains target product 1a (71.4mg, yield 75%). Illustrate that response time short raw material unreacted is complete.
Embodiment 13
Reactions steps and operation are with embodiment 1, and difference from Example 1 is in that, response time 23h. Stopped reaction, post-treated obtains target product 1a (49.5mg, yield 52%). Illustrate that extending the response time causes that product section decomposes.
Embodiment 14
Reactions steps and operation are with embodiment 1, and difference from Example 1 is in that, 3, the 3-bis-alkylthio group-2-propylene-1-ketone added in reaction system are 2b (48.1mg, 0.3mmol). Stopped reaction, post-treated obtains faint yellow solid target product 1b (79.5mg, yield 84%). Target product is measured by nuclear magnetic resoance spectrum and high resolution mass spectrum and is confirmed.
Embodiment 15
Reactions steps and operation are with embodiment 1, and difference from Example 1 is in that, 3, the 3-bis-alkylthio group-2-propylene-1-ketone added in reaction system are 2c (52.3mg, 0.3mmol). Stopped reaction, post-treated obtains faint yellow solid target product 1c (72.1mg, yield 73%). Target product is measured by nuclear magnetic resoance spectrum and high resolution mass spectrum and is confirmed.
Embodiment 16
Reactions steps and operation are with embodiment 1, and difference from Example 1 is in that, 3, the 3-bis-alkylthio group-2-propylene-1-ketone added in reaction system are 2d (67.3mg, 0.3mmol). Stopped reaction, post-treated obtains weak yellow liquid target product 1d (93.3mg, yield 82%). Target product is measured by nuclear magnetic resoance spectrum and high resolution mass spectrum and is confirmed.
Embodiment 17
Reactions steps and operation are with embodiment 1, and difference from Example 1 is in that, 3, the 3-bis-alkylthio group-2-propylene-1-ketone added in reaction system are 2e (91.0mg, 0.3mmol). Stopped reaction, post-treated obtains faint yellow solid target product 1e (134.7mg, yield 98%). Target product is measured by nuclear magnetic resoance spectrum and high resolution mass spectrum and is confirmed.
Embodiment 18
Reactions steps and operation are with embodiment 1, and difference from Example 1 is in that, 3, the 3-bis-alkylthio groups-propyl-2-alkene-1-ketone added in reaction system is 2f (64.3mg, 0.3mmol). Stopped reaction, post-treated obtains weak yellow liquid target product 1f (95.3mg, yield 86%). Target product is measured by nuclear magnetic resoance spectrum and high resolution mass spectrum and is confirmed.
Embodiment 19
Reactions steps and operation are with embodiment 1, and difference from Example 1 is in that, 3, the 3-bis-alkylthio group-2-propylene-1-ketone added in reaction system are 2g (84.1mg, 0.3mmol). Stopped reaction, post-treated obtains weak yellow liquid target product 1g (107.1mg, yield 82%). Target product is measured by nuclear magnetic resoance spectrum and high resolution mass spectrum and is confirmed.
Typical compound characterizes data
3,3-bis-alkylthio groups-2-phenylseleno-2-propylene-1-ketone derivatives (1a), faint yellow solid, fusing point 42-44 DEG C.1HNMR(400MHz,CDCl3,23��)��7.53-7.45and7.29-7.21(meach,2:3PH),2.40and2.29(seach,3:3H,2��CH3),2.06(s,3H,COCH3).13C{1H}NMR(100MHz,CDCl3, 23 DEG C) and �� 198.5 (Cq, C=O), 139.5and135.0 (Cq), 128.4 (Cq, COCSe), 134.9,129.5, and128.7 (CH), 30.5 (CH3CO),18.9,17.0(CH3).HRMSCacldforC12H14NaOS2Se[M+Na]+: 340.9549; Found:340.9556.
3,3-bis-alkylthio groups-2-phenylseleno-2-propylene-1-ketone derivatives (1d), faint yellow solid, fusing point 99-100 DEG C.1HNMR(400MHz,CDCl3,23��)��7.31-7.22(m,4H,aromaticCH),7.22-7.16(m,1H,aromaticCH),3.64and3.29(meach,2:2H,C(SCH2)2),2.42(s,3H,COCH3).13C{1H}NMR(100MHz,CDCl3, 23 DEG C) and �� 195.5 (Cq, C=O), 178.5and132.5 (Cq), 109.4 (Cq, COCSe), 129.6,128.7, and126.6 (CH), 41.6and35.2 (C (SCH2)2),28.9(CH3).HRMSCacldforC12H13OS2Se[M+H]+: 316.9573; Found:316.9572.
3,3-bis-alkylthio groups-2-phenylseleno-2-propylene-1-ketone derivatives (1f), faint yellow solid, fusing point 90-91 DEG C.1HNMR(400MHz,CDCl3, 23 DEG C) and �� 7.55 (m, 2H, aromaticCH), 7.41 (d, J=5.1Hz, 1H, aromaticCH), 7.29-7.18 (m, 4H, aromaticCH), 7.06 (dd, J=5.0,3.7Hz, 1H, aromaticCH), 7.48and6.44 (deach, J=15.7Hzeach, 1:1H, CCHCHCO), 2.49and2.31 (seach, 3:3H, 2 �� CH3).13C{1H}NMR(100MHz,CDCl3, 23 DEG C) and �� 190.0 (Cq, C=O), 140.0,138.2, and135.4 (Cq), (128.1 Cq, COCSe), 136.9,135.7,131.6,129.3,129.2,128.8,128.4, and125.4 (CH), 18.9and17.0 (CH3).HRMSCacldforC17H17ClOS2Se[M+H]+: 412.9606; Found:412.9617.
Claims (10)
1.3,3-bis-alkylthio group-2-phenylseleno-2-propylene-1-ketone derivatives, its structural formula 1 is as follows,
Substituent R1It is the alkyl of 1-4, aryl or aryl vinyl for carbon number; Wherein aryl is with the aryl of substituent group or heterocyclic aryl on phenyl, phenyl ring, and with the 1-5 kind that substituent group is in methyl, fluorine, chlorine, bromine, iodine, trifluoromethyl, nitro, cyano group, carboxyl on phenyl ring, the number of substituent group is 1-5;
Substituent R2It is the alkyl of 1-4, pi-allyl or benzyl for carbon number, orRepresent polymethylene (CH2)m, wherein m=2,3 or 4.
2. one kind 3, the synthetic method of 3-bis-alkylthio group-2-phenylseleno-2-propylene-1-ketone derivatives, it is characterized in that: with 3,3-bis-alkylthio group-2-propylene-1-ketone 2 is initiation material, by carrying out substitution reaction under acid catalysed conditions with organic selenium reagent 3, generate 3,3-bis-alkylthio group-2-phenylseleno-2-propylene-1-ketone derivatives 1; Synthetic route is such as shown in following reaction equation,
Wherein: organic selenium reagent 3 is diphenyl disenenide ether, phenylseleno chlorine or N-phenylseleno phthalimide; Acid catalyst is sulphuric acid, p-methyl benzenesulfonic acid, trifluoromethanesulfonic acid, trifluoroacetic acid, ferric chloride or aluminum chloride; The mol ratio of 3,3-bis-alkylthio group-2-propylene-1-ketone 2 and acid catalyst is 1:0.01-1:0.2; The mol ratio of 3,3-bis-alkylthio group-2-propylene-1-ketone 2 and organic selenium reagent 3 is 1:1-1:5; Response time is 1-24 hour; Reaction temperature is-20-60 DEG C.
3. the synthetic method described in claim 2, it is characterised in that:
3,3-bis-alkylthio group-2-propylene-1-ketone 2 react with organic selenium reagent 3, the most handy N-phenylseleno phthalimide of organic selenium reagent.
4. the synthetic method described in claim 2, it is characterised in that:
3,3-bis-alkylthio group-2-propylene-1-ketone 2 react with organic selenium reagent 3, the most handy p-methyl benzenesulfonic acid of catalyst.
5. the synthetic method described in claim 2, it is characterised in that:
3,3-bis-alkylthio group-2-propylene-1-ketone 2 is best with the reaction of organic selenium reagent 3 to carry out in dichloromethane or 1,2-dichloroethanes.
6. the synthetic method described in claim 2, it is characterised in that: the optimum molar ratio of 3,3-bis-alkylthio group-2-propylene-1-ketone 2 and acid catalyst is 1:0.05��1:0.1.
7. the synthetic method described in claim 2, it is characterised in that: the optimum molar ratio of 3,3-bis-alkylthio group-2-propylene-1-ketone 2 and organic selenium reagent 3 is 1:1��1:2.
8. the synthetic method described in claim 2, it is characterised in that: when 3,3-bis-alkylthio group-2-propylene-1-ketone 2 react with organic selenium reagent 3, optimum reacting time 4-6 hour; The optimum temperature that 3,3-bis-alkylthio group-2-propylene-1-ketone 2 reacts with organic selenium reagent 3 is 0��40 DEG C.
9. the synthetic method described in claim 2, it is characterised in that:
Reaction carries out product separation purification after terminating, and obtains 3,3-bis-alkylthio group-2-phenylseleno-2-propylene-1-ketone derivatives 1.
10. the synthetic method described in claim 2, it is characterised in that:
Reacting in organic solvent, organic solvent is one or more in methanol, ethanol, isopropanol, oxolane, Isosorbide-5-Nitrae-dioxane, dichloromethane, 1,2-dichloroethanes and toluene;
The 3,3-bis-alkylthio group-2-propylene-1-ketone 2 mass concentration in organic solvent is 1-2%.
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| US5876907A (en) * | 1993-10-08 | 1999-03-02 | Fuji Photo Film Co., Ltd. | Image formation method |
| CN1219127A (en) * | 1996-01-26 | 1999-06-09 | 纳特曼和希依有限公司 | Therapeutic anti-asthma agents containing selenium compounds |
| WO2002088128A1 (en) * | 2001-04-30 | 2002-11-07 | North Carolina State University | Rational syntheses of heteroleptic lanthanide sandwich coordination complexes |
| CN1923808A (en) * | 2006-09-22 | 2007-03-07 | 浙江大学 | Method of synthesizing E-beta-phenylseleno-gamma-carbonyl-alpha, beta-unsaturated acid ester |
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Patent Citations (4)
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| US5876907A (en) * | 1993-10-08 | 1999-03-02 | Fuji Photo Film Co., Ltd. | Image formation method |
| CN1219127A (en) * | 1996-01-26 | 1999-06-09 | 纳特曼和希依有限公司 | Therapeutic anti-asthma agents containing selenium compounds |
| WO2002088128A1 (en) * | 2001-04-30 | 2002-11-07 | North Carolina State University | Rational syntheses of heteroleptic lanthanide sandwich coordination complexes |
| CN1923808A (en) * | 2006-09-22 | 2007-03-07 | 浙江大学 | Method of synthesizing E-beta-phenylseleno-gamma-carbonyl-alpha, beta-unsaturated acid ester |
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