CN109020989B - Synthesis method of trifluoromethyl substituted 2-methyl dihydrofuran chroman skeleton compound - Google Patents
Synthesis method of trifluoromethyl substituted 2-methyl dihydrofuran chroman skeleton compound Download PDFInfo
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Abstract
The invention develops a simple reaction of 2-methyl dihydrofurochroman derivatives and trifluoroacetonate under the catalysis of Bronsted acid, and realizes C (sp) in a 2-methyl form3) -H functionalization, the resulting trifluoromethyl modified 2-methyl dihydro chroman compound is obtained in good yield and excellent diastereoselectivity. The method realizes unique and efficient regioselectivity control, has the advantages of mild reaction conditions, high reaction speed, high yield, no metal, simple operation, good selectivity, good substrate universality and the like, and provides important experimental basis and theoretical basis for modification of 2-methyldihydrofuranchroman compounds. The invention synthesizes a novel skeleton compound with methyl-substituted trifluoromethyl group and chroman structure through molecular design and optimization.
Description
Technical Field
the invention belongs to the technical field of chemical synthesis, and particularly relates to a method for synthesizing a trifluoromethyl-substituted 2-methyl dihydrofuran chroman skeleton compound.
Background
The compounds containing chroman skeleton and trifluoromethyl group are rich in variety and widely exist in artificially synthesized molecules such as natural products, medicines, chemical raw materials and the like. For example, bw638c is useful as a rhinovirus replication inhibitor; troglitazone is used for the treatment of diabetes; centchroman is an effective contraceptive agent; retrovertextractase as an HIV-1 inhibitor; antidepsant is clinically used as an inhibitor of adult depression; casodex is used for treating advanced prostate cancer and the like.
the trifluoromethyl group-containing compound can be synthesized by a Friedel-Crafts alkylation reaction, an aldol condensation reaction, a Carbonyl-ene reaction (Carbonyl-ene reaction) or the like, which is usually an active reaction substrate, using a trifluoroketoester.
in 2004, the Koichi Mikami group reported that a trifluoromethyl-substituted cyclopentene compound was constructed by a carbonyl-ene reaction of an olefin catalyzed by a transition metal Pd with a trifluoroketonate (Tetrahedron: Asymmetry 2004,15, 3885-.
In 2008, Magnus Rueping topic group developed a series of trifluoromethyl-substituted styrene compounds by carbonyl-ene reaction of styrene compounds with trifluoroketonic acid ester under catalysis of chiral bronsted acid (angelw.chem.int.ed.2008, 47, 6798-6801).
in 2009, Teck-Peng Long topic group developed an indium trichloride-Pybox catalyzed carbonyl-ene reaction of olefins with trifluorketonates.
The above mechanism of carbonyl-ene reaction of a trifluoroketoester with an olefin can be summarized as follows: the olefin C1 attacks the carbonyl group of the triflate, the C2 forms a carbenium ion, and then the C3 position loses a proton, formally after addition, the double bond of the olefin is shifted. Although the above reactions have obvious advantages, the reaction mode is relatively fixed, namely the attack site of the trifluoroketonic acid ester is fixed, and the position of the double bond of the generated olefin product is also fixed. This limits the application range of this type of reaction to a large extent, limiting the exploration of trifluoromethyl modified backbones.
At present, 2-methyl dihydrofuran compounds are rarely researched, and especially, the research on 2-methyl dihydrofuran chroman compounds with a brand-new framework is not reported, and two isomers can exist under an acidic condition. There is then a significant mechanistic challenge when such compounds undergo carbonyl-ene reactions with triflates: two attack possibilities arise, i.e. whether C1 attacks the trifluoroacetate carbonyl or C3 attacks the trifluoroacetate carbonyl. These two possibilities lead to completely different regioselectivities, yielding at least two possible products.
In order to solve the problems in organic synthesis methodologies, to realize the control of carbonyl-ene reaction regioselectivity involving trifluoroketoester, and to construct trifluoromethyl-substituted 2-methyldihydrofurochroman compounds, it is necessary to develop a reaction of trifluoroketoester with 2-methyldihydrofurochroman compounds.
Disclosure of Invention
The invention aims to provide a method for synthesizing a trifluoromethyl-substituted 2-methyl dihydrofurochroman skeleton compound. The method has the advantages of simple and practical operation, good yield, green and economical reaction and environmental friendliness.
The synthesis method provided by the invention comprises the following steps:
reacting 2-methyl dihydrofurochroman derivative with trifluoroacetate, and preparing a trifluoromethyl-substituted 2-methyl dihydrofurochroman framework compound under the action of a catalyst.
The trifluoromethyl substituted 2-methyl dihydrofurochroman skeleton compound is a compound shown as a formula I:
In the formula I, the compound has the following structure,
R1Is selected from C1-C3Alkyl radical, C1-C3any one of alkoxy and halogen;
R2Is selected from any one of phenyl and thienyl.
the specific reaction formula of the above reaction is shown as follows:
wherein the compound shown in the formula II is a 2-methyl dihydrofurochroman derivative:
In the formula II, the reaction solution is shown in the specification,
R1is selected from C1-C3Alkyl radical, C1-C3any one of alkoxy and halogen;
R2Is selected from any one of phenyl and thienyl.
The catalyst is any one of methanesulfonic acid, trifluoromethanesulfonic acid, copper trifluoromethanesulfonate, scandium trifluoromethanesulfonate, trifluoroacetic acid, S-binaphthol phosphate, camphorsulfonic acid, acetic acid and benzoic acid.
the above reaction requires a dehydration assistant, specificallyand (3) a molecular sieve.
The above reaction is carried out in the presence of a solvent which is inert to the reaction. Such a solvent is generally an aprotic solvent, and may be a polar solvent or a nonpolar solvent. Specifically any one of dichloromethane, 1, 2-dichloroethane, tetrahydrofuran, toluene and acetonitrile.
The molar ratio of the 2-methyl dihydrofurochroman derivative to the trifluoroacetonate is 1: 1.5.
The above reaction was carried out at 25 ℃.
The invention provides a synthesis method of a trifluoromethyl substituted 2-methyl dihydrofuran chroman skeleton compound, which specifically comprises the following steps:
0.1mmol of 2-methyl dihydrofurochroman derivative,Molecular sieves 50mg were added to 1mL of toluene, followed by addition of 0.15mmol of trifluoroketonate and 20 mol% of S-binaphthol phosphate to the toluene; controlling the temperature of the system to be 25 ℃ at room temperature, continuously stirring, and carrying out sample application tracking reaction by a thin layer chromatography plate until the reaction of the raw materials is complete;
After the reaction is finished, separating a reaction product in the solution by using a silica gel column, and performing rotary evaporation and concentration to obtain a product.
the compounds to which the present invention relates may exist in the form of one or more stereoisomers. The various isomers include enantiomers, diastereomers, geometric isomers. It is within the scope of the present invention for these isomers to include mixtures of these isomers.
In the reaction process of the invention, firstly, 2-methyl dihydrofuran chroman is isomerized under the action of Bronsted acid to shift the position of a double bond to the position of the original methyl, and then the 2-methyl dihydrofuran chroman and the trifluoromethyl ketonic acid ester are subjected to carbonyl-alkene reaction to obtain a target product. Comparing the starting material and the product, it was found that this reaction achieved C (sp) in the 2-methyl form3) -H functionalization, a trifluoromethyl substituted dihydrofurochroman compound is synthesized. More importantly, compared with the traditional carbonyl-alkene reaction, the reaction realizes unique and efficient regioselectivity control, and synthesizes the product with 3-substituted position different from the conventional product.
The traditional carbonyl-ene reaction mechanism:
The reaction mechanism of the present invention:
The invention develops a simple reaction of the 2-methyl dihydrofurochroman derivative and trifluoroacetonate under the catalysis of Bronsted acid, and the finally obtained trifluoromethyl modified 2-methyl dihydrochroman compound has better yield and excellent diastereoselectivity. The method has the advantages of mild reaction conditions, high reaction speed, high yield, no metal, simple operation, good selectivity, good substrate universality and the like, and provides important experimental basis and theoretical basis for the modification of the 2-methyl dihydrofuranchroman compounds. The invention synthesizes a novel skeleton compound with methyl-substituted trifluoromethyl group and chroman structure through molecular design and optimization.
Detailed Description
The foregoing aspects of the present invention are further illustrated by the specific embodiments provided in the following examples, which should not be construed as limiting the scope of the above-described subject matter of the present invention to the following examples by those skilled in the art; all the technologies realized based on the above contents of the present invention belong to the scope of the present invention.
The experimental methods used in the following examples are all conventional methods unless otherwise specified; reagents, materials, instruments and the like used in the following examples are commercially available unless otherwise specified.
Example 1
2-methyl dihydrofurochroman (0.1mmol),molecular sieves (50mg) were added to 1mL of the solvent, followed by addition of the trifluoroketoester (0.15mmol) and the catalyst to the solvent.
The temperature of the system is controlled to be 25 ℃ at room temperature, the stirring is continued, and the sample application tracking reaction is carried out through a thin layer chromatography plate until the reaction of the raw materials is completed.
after the reaction is finished, separating a reaction product in the solution by using a silica gel column, and performing rotary evaporation and concentration to obtain a product.
Using the above equation, 14 parallel test sets were set up using different catalysts, solvents and reaction times. The catalysts are respectively methanesulfonic acid CH3SO3H. TfOH trifluoromethanesulfonate copper trifluoromethanesulfonate Cu (OTf)2Scandium trifluoromethanesulfonate Sc (OTf)3TFA, S-binaphthol phosphate PA, camphorsulfonic acid CSA, AcOH acetate, Benzoic acid. The solvent is dichloromethane DCM, 1, 2-dichloroethane DCE, tetrahydrofuran THF, toluene tolumene and acetonitrile CH respectively3and (C) CN. The specific catalysts, solvent types and concentrations used in the test groups are shown in table 1:
TABLE 1 reaction yield of 2-methyldihydrofurochroman with triflate
According to the analysis of the parallel test results, under the catalysis of 20mol percent PA, toluene is used as a solvent,molecular sieve as additive, and stirring at 25 deg.C for 3 hr to obtain 91% yield and 2.4:1 diastereoselectivity.
In the following examples 2 to 7, according to the procedure of example 1, the molar ratio of the starting 2-methyldihydrofurochroman derivative to trifluoropyruvic acid in the reaction system was 1:1.5, toluene was used as a solvent, and 20 mol% of PA andMolecular sieves (0.1mmol 2-methyldihydrofurochroman corresponds tomolecular sieve) at 25 deg.C until the reaction of the raw materials is complete.
Example 2
The product is as follows: the chemical formula is as follows: c23H21F3O5
Molecular weight: 434.1341
Structural formula (xvi):
Yield: 90 percent; dr 2.4:1
1H NMR(500MHz,CDCl3)δ7.48–7.33(m,5H),7.14(t,J＝7.6Hz,1H),6.87(dd,J＝16.0,7.8Hz,2H),6.71(d,J＝7.5Hz,1H),5.18(d,J＝2.4Hz,1H),4.98(d,J＝2.2Hz,1H),3.96(s,1H),3.73(s,3H),3.68(s,1H),2.77(d,J＝14.3Hz,1H),2.64(d,J＝14.3Hz,1H),1.22(s,3H).13C NMR(125MHz,CDCl3)δ168.86,155.99,154.25,136.08,131.34,129.22,128.36,127.52,127.43,127.27,123.02(q,J＝284.6Hz),122.03,118.31,101.30,90.89,88.44,75.62(q,J＝29.3Hz),54.27,49.50,31.24,23.55.
Example 3
The product is as follows: the chemical formula is as follows: c24H23F3O5
Molecular weight: 448.1498
Structural formula (xvi):
yield: 94 percent; dr 2.1:1
1H NMR(500MHz,CDCl3)δ7.45–7.35(m,5H),6.92(d,J＝7.9Hz,1H),6.78(d,J＝8.0Hz,1H),6.50(s,1H),5.14(d,J＝2.4Hz,1H),4.96(d,J＝2.2Hz,1H),3.93(s,1H),3.73(s,3H),3.70(s,1H),2.78(d,J＝14.2Hz,1H),2.64(d,J＝14.2Hz,1H),2.16(s,3H),1.20(s,3H).13C NMR(125MHz,CDCl3)δ168.88,155.83,151.88,136.22,131.34,128.87,128.34,127.94,127.67,127.46,123.05(q,J＝284.6Hz),117.96,101.37,90.87,88.36,75.59(q,J＝29.4Hz),54.25,49.58,31.28,23.60,20.97.
Example 4
The product is as follows: the chemical formula is as follows: c24H23F3O6
Molecular weight: 464.1447
structural formula (xvi):
Yield: 91%; dr 2:1
1H NMR(500MHz,CDCl3)δ7.47–7.32(m,5H),6.81(d,J＝8.6Hz,1H),6.66(dd,J＝8.6,2.9Hz,1H),6.33–6.28(m,1H),5.13(d,J＝2.5Hz,1H),4.95(d,J＝2.4Hz,1H),3.95(s,1H),3.74(s,3H),3.73(s,1H),3.64(s,3H),2.77(d,J＝14.3Hz,1H),2.64(d,J＝14.3Hz,1H),1.20(s,3H).13C NMR(125MHz,CDCl3)δ168.92,155.84,154.74,147.77,135.88,131.23,130.54,128.39,127.57,123.02(q,J＝284.5Hz),118.60,114.17,111.28,101.28,90.75,88.51,75.48(q,J＝29.4Hz),55.51,54.32,49.76,31.22,23.51.
Example 5
The product is as follows: the chemical formula is as follows: c23H20ClF3O5
molecular weight: 468.0951
Structural formula (xvi):
yield: 88 percent; dr 2.1:1
1H NMR(500MHz,CDCl3)δ7.48–7.36(m,5H),7.09(dd,J＝8.4,2.3Hz,1H),6.82(d,J＝8.4Hz,1H),6.68(s,1H),5.17(d,J＝2.4Hz,1H),4.98(d,J＝2.3Hz,1H),3.92(s,1H),3.75(s,4H),2.79(d,J＝14.3Hz,1H),2.66(d,J＝14.3Hz,1H),1.20(s,3H).13C NMR(125MHz,CDCl3)δ168.94,156.18,152.90,135.21,131.16,131.06,128.60,127.86,127.42,127.22,127.17,122.99(q,J＝284.5Hz),119.57,101.32,90.63,88.63,75.42(q,J＝29.5Hz),54.37,49.44,31.12,23.40.
Example 6
The product is as follows: the chemical formula is as follows: c23H20BrF3O5
Molecular weight: 512.0446
structural formula (xvi):
Yield: 90 percent; dr 2.1:1
1H NMR(500MHz,CDCl3)δ7.48–7.36(m,5H),7.24(dd,J＝8.4,1.9Hz,1H),6.81(dd,J＝2.2,1.1Hz,1H),6.77(d,J＝8.4Hz,1H),5.17(d,J＝2.6Hz,1H),4.98(d,J＝2.4Hz,1H),3.92(s,1H),3.74(s,4H),2.79(d,J＝14.3Hz,1H),2.66(d,J＝14.3Hz,1H),1.20(s,3H).13C NMR(125MHz,CDCl3)δ168.95,156.19,153.46,135.16,131.50,131.15,130.24,130.21,128.61,127.87,122.99(q,J＝284.5Hz),120.07,114.72,101.33,90.65,88.58,75.40(q,J＝29.6Hz),54.37,49.39,31.13,23.40.
Example 7
The product is as follows: the chemical formula is as follows: c21H19F3O5S
Molecular weight: 440.0905
Structural formula (xvi):
Yield: 90 percent; dr 2.4:1
1H NMR(500MHz,CDCl3)δ7.39–7.33(m,1H),7.14(t,J＝7.6Hz,1H),7.12–7.07(m,2H),6.90(t,J＝7.5Hz,1H),6.87(d,J＝7.9Hz,1H),6.76(d,J＝7.6Hz,1H),5.19(d,J＝2.4Hz,1H),4.95(d,J＝2.4Hz,1H),4.34(s,1H),3.79(s,3H),3.71(s,1H),2.76(d,J＝14.3Hz,1H),2.64(d,J＝14.3Hz,1H),1.33(s,3H).13C NMR(125MHz,CDCl3)δ168.76,156.09,153.83,137.47,129.22,128.85,127.56,127.41,126.71,125.70,122.98(q,J＝284.6Hz),122.32,118.20,101.39,90.51,88.32,75.69(q,J＝29.4Hz),54.36,44.97,31.24,23.44.
The foregoing is directed to preferred embodiments of the present invention, other and further embodiments of the invention may be devised without departing from the basic scope thereof, and the scope thereof is determined by the claims that follow. However, any simple modification, equivalent change and modification of the above embodiments according to the technical essence of the present invention are within the protection scope of the technical solution of the present invention.
Claims (4)
1. A method for synthesizing trifluoromethyl substituted 2-methyl dihydrofuran chroman skeleton compound is characterized in that:
Reacting 2-methyl dihydrofurochroman derivatives with trifluoroacetate to prepare trifluoromethyl-substituted 2-methyl dihydrofurochroman skeleton compounds under the action of a catalyst;
The trifluoromethyl substituted 2-methyl dihydrofurochroman skeleton compound is a compound shown as a formula I:
In the formula I, the compound has the following structure,
R1is selected from C1-C3Alkyl radical, C1-C3Any one of alkoxy and halogen;
R2Any one of phenyl and thienyl;
the specific reaction formula of the reaction is as follows:
wherein the compound shown in the formula II is a 2-methyl dihydrofurochroman derivative:
In the formula II, the reaction solution is shown in the specification,
R1is selected from C1-C3alkyl radical, C1-C3Any one of alkoxy and halogen;
R2Any one of phenyl and thienyl;
the catalyst is any one of methanesulfonic acid, trifluoromethanesulfonic acid, copper trifluoromethanesulfonate, trifluoroacetic acid, S-binaphthol phosphate, camphorsulfonic acid, acetic acid and benzoic acid;
The reaction requires a dehydration assistant, specificallyA molecular sieve;
The reaction is carried out in the presence of a solvent, and is any one of dichloromethane, 1, 2-dichloroethane, tetrahydrofuran, toluene and acetonitrile.
2. the method for synthesizing a trifluoromethyl-substituted 2-methyldihydrofurochroman skeleton compound according to claim 1, characterized in that: the molar ratio of the 2-methyl dihydrofurochroman derivative to the trifluoroacetonate is 1: 1.5.
3. The method for synthesizing a trifluoromethyl-substituted 2-methyldihydrofurochroman skeleton compound according to claim 2, characterized in that: the reaction is carried out at 25 ℃.
4. A method for synthesizing a trifluoromethyl substituted 2-methyldihydrofurochroman skeleton compound according to any one of claims 1 to 3, characterized in that: the method specifically comprises the following steps:
adding 0.1mmol of 2-methyl dihydrofurochroman derivative and 50mg of molecular sieve into 1mL of toluene, and then adding 0.15mmol of trifluoroketonic acid ester and 20 mol% of S-binaphthol phosphate into the toluene; controlling the temperature of the system to be 25 ℃ at room temperature, continuously stirring, and carrying out sample application tracking reaction by a thin layer chromatography plate until the reaction of the raw materials is complete;
after the reaction is finished, separating a reaction product in the solution by using a silica gel column, and performing rotary evaporation and concentration to obtain a product.
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