CN116239471A - Synthesis method of polysubstituted 1, 3-butadiene compound - Google Patents

Synthesis method of polysubstituted 1, 3-butadiene compound Download PDF

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CN116239471A
CN116239471A CN202310277046.7A CN202310277046A CN116239471A CN 116239471 A CN116239471 A CN 116239471A CN 202310277046 A CN202310277046 A CN 202310277046A CN 116239471 A CN116239471 A CN 116239471A
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polysubstituted
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司雯
宋然
吕健
冯威
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Qingdao University of Science and Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C07C67/32—Decarboxylation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

The invention discloses a method for synthesizing a polysubstituted 1, 3-butadiene compound, belonging to the field of organic synthesis. The structural formula of the polysubstituted 1, 3-butadiene compound is shown as formula I. The method involves decarboxylation hydrogen transfer of GMDVs compounds of formula (II) in the presence of palladium tetraphenylphosphine, phenols and R-BINAP under nitrogen protection. The method used in the invention has the following advantages compared with the traditional method: 1) The yield is high, the atom economy is good, and the stereoselectivity is excellent; 2) The substrate has good universality, and can be used for carrying out diversified synthesis on polysubstituted 1, 3-butadiene compounds; 3) The catalyst dosage is low, the raw materials do not need complex pre-functionalization process, the post-treatment is convenient, the product is easy to separate and purify, and the mass production is easy.

Description

Synthesis method of polysubstituted 1, 3-butadiene compound
Technical Field
The invention belongs to the field of organic synthesis, and mainly relates to a synthesis method of a polysubstituted 1, 3-butadiene compound.
Background
Polysubstituted 1, 3-butadienes are widely found in natural products and bioactive molecules that are closely related to human health, such as Vitamin A, JBIR-23/24 and Trichostatin A. In addition, polysubstituted 1, 3-butadiene-based compounds are also common synthetic blocks for adiponitrile, a key intermediate for water-resistant coatings and nylon-based products. Some important chemical transformations, such as cycloaddition or polyfunctionalization processes, are also often carried out by selecting 1, 3-butadiene as starting substrate.
Traditional methods for synthesizing polysubstituted 1, 3-butadiene compounds comprise elimination reaction and Wittig olefin synthesis reaction, but the Z/E configuration of double bonds cannot be well controlled by the two types of conversion, and subsequent separation is needed to obtain a single selective product. In recent years chemists have developed a range of stereoselective synthetic methods including hydrocarbon activation, cross-coupling, ene-alkyne metathesis reactions, etc., but often require pre-functionalization of the starting materials and are less atom economical. In view of the importance of polysubstituted 1, 3-butadiene compounds in chemical synthesis, biological research and industrial application, it is particularly important to develop a strategy with high efficiency, high stereoselectivity and good atomic economy.
Disclosure of Invention
The invention aims to overcome the problems of substrate limitation and low atom economy in the existing synthesis method of polysubstituted 1, 3-butadiene compounds, and provides a high-efficiency diversified synthesis method of polysubstituted 1, 3-butadiene compounds, which has the advantages of convenient and easily available substrate and economical reaction atoms.
In order to achieve the above object, the present invention provides a method for preparing a polysubstituted 1, 3-butadiene-based compound represented by formula (I), comprising: decarboxylation hydrogen transfer of GMDVs compound shown in formula (II) under nitrogen protection in the presence of tetraphenylphosphine palladium, phenols and R-BINAP.
Figure BDA0004136750000000021
Wherein R is 1 Is one of methyl, ethyl and tert-butyl; r is R 2 Methyl, benzyl, naphthyl, thienyl and substituted or unsubstitutedOne of the substituted phenyl groups; the substituent is one of halogen atom, methyl, methoxy or phenyl and is positioned at the 2, 3 and 4 positions of the benzene ring.
Preferably, the phenol is one of phenol, p-nitrophenol, p-methoxyphenol, p-methylphenol and o-methylphenol.
Preferably, the amount of the tetraphenylphosphine palladium is 1 to 10 parts by mole and the amount of the phenol is 50 to 150 parts by mole, relative to 100 parts by mole of the GMDVs-type compound; the amount of R-BINAP is 1 to 10 parts by mole.
Preferably, the decarboxylation hydrogen transfer reaction of the GMDVs compound is carried out at a temperature of 90-110 ℃ for 12-24 hours under stirring.
Preferably, column chromatography is performed with a mixed solvent of petroleum ether and ethyl acetate after the reaction.
Compared with the prior report, the preparation method for synthesizing the polysubstituted 1, 3-butadiene compound has the following remarkable advantages:
(1) The yield is high, the atom economy is good, and the stereoselectivity is excellent;
(2) The substrate has good universality, and can be used for carrying out diversified synthesis on polysubstituted 1, 3-butadiene compounds;
(3) The catalyst dosage is low, the raw materials do not need complex pre-functionalization process, the post-treatment is convenient, the product is easy to separate and purify, and the mass production is easy.
Drawings
FIG. 1 is an NMR chart of compound 2a prepared in example 1;
FIG. 2 is an NMR spectrum of compound 2b prepared in example 2;
FIG. 3 is an NMR spectrum of compound 2c prepared in example 3;
FIG. 4 is an NMR spectrum of compound 2d prepared in example 4;
FIG. 5 is an NMR spectrum of compound 2e prepared in example 5;
FIG. 6 is an NMR spectrum of compound 2f prepared in example 6;
FIG. 7 is an NMR spectrum of 2g of the compound prepared in example 7;
FIG. 8 is an NMR spectrum of compound 2h prepared in example 8;
Detailed Description
The method of the present invention is described herein by way of specific examples, but the present invention is not limited to the description of the embodiments, and any modification, equivalent substitution, improvement, etc. are intended to be included in the scope of the present invention.
The method for synthesizing the polysubstituted 1, 3-butadiene compound comprises the following steps: decarboxylation of GMDVs compounds was transferred under nitrogen in the presence of tetraphenylphosphine palladium, phenols and R-BINAP.
In the invention, the structure of the GMDVs compound is shown as a formula (II).
Figure BDA0004136750000000031
In formula (II), R 1 Is one of methyl, ethyl and tert-butyl; r is R 2 Is one of methyl, benzyl, naphthyl, thienyl and substituted or unsubstituted phenyl; the substituent is one of halogen atom, methyl, methoxy or phenyl and is positioned at the 2, 3 and 4 positions of the benzene ring.
In the method of the present invention, the amount of the tetraphenylphosphine palladium used is 1 to 10 parts by mole, more preferably 1 to 5 parts by mole, most preferably 5 parts by mole, relative to 100 parts by mole of the GMDVs-based compound; the amount of phenols used is 50 to 150 parts by mole, more preferably 50 to 100 parts by mole, most preferably 100 parts by mole; the amount of R-BINAP used is 1 to 10 parts by mole, more preferably 1 to 5 parts by mole, and most preferably 5 parts by mole.
In the method of the invention, the phenol is one of phenol, p-nitrophenol, p-methoxyphenol, p-methylphenol and o-methylphenol.
In the method of the present invention, preferably, the decarboxylation hydrogen transfer reaction of the GMDVs-type compound is carried out at a temperature of 90 to 110 ℃ with stirring for 12 to 24 hours.
In the method according to the present invention, in order to obtain a pure target product, the method preferably further comprises: performing column chromatography with mixed solution of petroleum ether and ethyl acetate after the reaction; in the mixed solvent of petroleum ether and ethyl acetate, the volume ratio of petroleum ether to ethyl acetate can be 30-80:1, preferably 40-60:1, and most preferably 50:1.
In one embodiment, the method of synthesizing a polysubstituted 1, 3-butadiene-based compound comprises:
(1) Adding tetraphenylphosphine palladium into a reactor according to the amount of 1-10mol% of GMDVs under the protection of nitrogen;
(2) Adding R-BINAP into the reactor of the step (1) according to the amount of 1-10mol% of GMDVs under the protection of nitrogen;
(3) Adding phenols into the reactor of the (1) according to the amount of 50-150mol% of GMDVs under the protection of nitrogen;
(4) Under the protection of nitrogen, adding GMDVs into the reactor of the step (1);
(5) Adding a reaction solvent into the reactor of the step (1) under the protection of nitrogen, wherein the solvent is one of diethyl ether, tetrahydrofuran, methyl tertiary butyl ether and 1, 4-dioxane;
(6) Under the protection of nitrogen, the reaction is stirred for 12 to 24 hours at the temperature of 90 to 110 ℃ to purify the target product.
The invention is described in further detail below by way of examples:
example 1
The reaction equation is as follows:
Figure BDA0004136750000000041
tetratriphenylphosphine palladium (2.5 mmol), R-BINAP (2.5 mmol), p-nitrophenol (50 mmol) and compound 1a (50 mmol) were added to the reactor under nitrogen, then 500mL of diethyl ether was added, and the mixture was stirred at 100℃for 18 hours to complete the reaction. And (3) performing column chromatography by using a mixed solvent of petroleum ether and ethyl acetate in a volume ratio of 50:1 to obtain pure 2a. The yield of 2a was 90%, E/z=50:1.
2a 1 The H NMR data are as follows: 1 H NMR(500MHz,CDCl 3 ):δ7.52(s,1H),7.24(t,J＝7.5Hz,1H),7.16(dd,J＝16.6,7.9Hz,2H),7.06(d,J＝7.4Hz,1H),5.25(s,1H),5.19(s,1H),3.72(s,3H),2.17(s,3H),1.31(s,3H)ppm.
2a 13 The C NMR data are as follows: 13 C NMR(125MHz,CDCl 3 ):δ168.42,142.96,141.11,136.86,135.73,131.02,130.09,129.52,127.95,125.24,125.21,52.29,20.59,19.81ppm.
example 2
The reaction equation is as follows:
Figure BDA0004136750000000051
tetratriphenylphosphine palladium (2.5 mmol), R-BINAP (2.5 mmol), phenol (50 mmol) and compound 1b (50 mmol) were added to the reactor under nitrogen, and then 500mL of tetrahydrofuran was added thereto, followed by stirring at 100℃for 18 hours, and the reaction was completed. And (3) performing column chromatography by using a mixed solvent with the volume ratio of petroleum ether to ethyl acetate being 50:1 to obtain pure 2b.2b was produced in 76% yield, E/z=7:1.
2b 1 The H NMR data are as follows: 1 H NMR(500MHz,CDCl 3 ):δ7.49(s,1H),7.36(d,J＝6.5Hz,0.28H),7.28(dd,J＝20.0,11.7Hz,2H),7.19(s,1H),7.12(d,J＝6.5Hz,0.28H),7.08(d,J＝7.3Hz,1H),6.53(s,0.14H),5.27(s,1H),5.23(s,1H),5.20(s,0.14H),5.17(s,0.14H),3.83(s,0.42H),3.74(s,3H),1.92(s,0.42H),1.40(s,3H)ppm.
2b 13 The C NMR data are as follows: 13 C NMR(125MHz,CDCl 3 ):δ167.95,143.54,140.50,137.81,133.61,130.36,130.12,128.94,128.33,127.82,125.73,52.37,21.30ppm.
example 3
The reaction equation is as follows:
Figure BDA0004136750000000061
tetratriphenylphosphine palladium (2.5 mmol), R-BINAP (2.5 mmol), p-methoxyphenol (50 mmol) and compound 1c (50 mmol) were added to the reactor under nitrogen, then 500mL of 1, 4-dioxane was added, and the mixture was stirred at 100℃for 18 hours, followed by completion of the reaction. And (3) performing column chromatography by using a mixed solvent with the volume ratio of petroleum ether to ethyl acetate being 50:1 to obtain pure 2c. The yield of 2c was 98%, E/z=4:1.
2c 1 The H NMR data are as follows: 1 H NMR(500MHz,CDCl 3 ):δ7.46(s,1H),7.30(d,J＝8.6Hz,0.46H),7.11(d,J＝8.4Hz,2H),6.87(d,J＝8.4Hz,2.46H),6.46(s,0.23H),5.25(s,1H),5.19(s,1H),5.15(s,0.23H),5.10(s,0.23H),3.82(s,3H),3.81(s,1.38H),3.74(s,3H),1.92(s,0.69H),1.41(s,3H)ppm.
2c 13 The C NMR data are as follows: 13 C NMR(125MHz,CDCl 3 ):δ167.78,158.14,141.68,140.14,130.48,130.30,130.20,127.12,126.40,123.61,118.65,113.11,112.19,54.17,51.23,20.23,19.11ppm.
example 4
The reaction equation is as follows:
Figure BDA0004136750000000062
tetratriphenylphosphine palladium (2.5 mmol), R-BINAP (2.5 mmol), p-methylphenol (50 mmol) and compound 1d (50 mmol) were added to the reactor under nitrogen, then methyl tert-butyl ether 500mL was added and stirred at 100deg.C for 18 hours to complete the reaction. And (3) performing column chromatography by using a mixed solvent of petroleum ether and ethyl acetate in a volume ratio of 50:1 to obtain pure 2d. The yield of 2d was 70%, E/z=10:1.
2d 1 The H NMR data are as follows: 1 H NMR(500MHz,CDCl 3 ):δ7.56(d,J＝7.5Hz,2H),7.50(d,J＝8.1Hz,2.2H),7.44(s,1H),7.37(t,J＝7.6Hz,2.5H),7.28(d,J＝7.4Hz,1H),7.21-7.18(m,2.2H),6.54(s,0.1H),5.21(s,1H),5.14(s,1.1H),5.09(s,0.1H),3.79(s,0.3H),3.69(s,3H),1.88(s,0.3H),1.37(s,3H)ppm.
2d 13 The C NMR data are as follows: 13 C NMR(125MHz,CDCl 3 ):δ168.53,143.01,140.98,140.69,140.42,135.00,131.51,130.51,128.76,127.36,127.06,126.37,125.00,52.32,21.33ppm.
example 5
The reaction equation is as follows:
Figure BDA0004136750000000071
tetratriphenylphosphine palladium (2.5 mmol), R-BINAP (2.5 mmol), o-methylphenol (50 mmol) and compound 1e (50 mmol) were added to the reactor under nitrogen, then 500mL of diethyl ether was added and stirred at 100deg.C for 18 hours to complete the reaction. And (3) performing column chromatography by using a mixed solvent with the volume ratio of petroleum ether to ethyl acetate being 50:1 to obtain pure 2e.2E was 99% yield, E/z=3:1.
2e 1 The H NMR data are as follows: 1 H NMR(500MHz,CDCl 3 ):δ7.48(s,1H),7.29–7.27(m,1H),7.20-7.17(m,0.53H),7.15(d,J＝5.1Hz,0.23H),7.11(s,1H),6.98(d,J＝4.7Hz,1H),6.94(d,J＝5.1Hz,0.23H),6.57(s,0.33H),5.27(s,1H),5.22(s,1H),5.16(s,0.33H),5.12(s,0.33H),3.84(s,1H),3.75(s,3H),1.91(s,1H),1.47(s,3H)ppm.
2e 13 The C NMR data are as follows: 13 C NMR(125MHz,CDCl 3 ):δ169.81,168.24,143.71,141.00,140.60,138.04,135.35,133.48,131.64,129.59,129.20,128.50,127.41,127.17,126.69,126.52,126.24,125.13,124.92,124.74,124.46,122.57,121.87,120.09,117.01,52.28,52.13,20.58,20.05ppm.
example 6
The reaction equation is as follows:
Figure BDA0004136750000000081
tetratriphenylphosphine palladium (2.5 mmol), R-BINAP (2.5 mmol), p-nitrophenol (50 mmol) and compound 1f (50 mmol) were added to the reactor under nitrogen, then 500mL of diethyl ether was added, and the mixture was stirred at 100℃for 18 hours to complete the reaction. And (3) performing column chromatography by using a mixed solvent with the volume ratio of petroleum ether to ethyl acetate being 50:1 to obtain pure 2f. The yield of 2f was 76%, E/z=50:1.
2f 1 The H NMR data are as follows: 1 H NMR(500MHz,DMSO-d6):δ7.86(dd,J＝12.3,5.1Hz,2H),7.76(s,1H),7.72(d,J＝8.7Hz,1H),7.50-7.43(m,3H),7.30(d,J＝6.9Hz,1H),5.31(s,1H),5.16(s,1H),3.66(s,3H),1.13(s,3H)ppm.
2f 13 The C NMR data are as follows: 13 C NMR(125MHz,CDCl 3 ):δ167.73,143.48,140.13,132.76,132.16,131.74,128.73,127.29,127.18,126.73,125.26,124.78,124.45,123.94,51.32,19.39ppm.
example 7
The reaction equation is as follows:
Figure BDA0004136750000000082
tetratriphenylphosphine palladium (2.5 mmol), R-BINAP (2.5 mmol), p-nitrophenol (50 mmol) and 1g (50 mmol) of the compound were charged into a reactor under nitrogen, 500mL of diethyl ether was added thereto, and the mixture was stirred at 100℃for 18 hours to complete the reaction. Column chromatography with a 50:1 volume ratio of petroleum ether to ethyl acetate in a mixed solvent gave pure 2g. The yield of 2g was 96%, E/z=13:1.
2g of 1 The H NMR data are as follows: 1 C NMR(500MHz,CDCl 3 ):δ7.34(s,1H),7.29-7.24(m,2.24H),7.16(dd,J＝13.7,7.3Hz,3.16H),6.08(s,0.08H),5.19-5.16(m,1H),5.12(s,1H),4.99(s,0.08H),4.95(s,0.08H),3.90(s,2H),3.80(s,0.16H),3.70-3.67(m,3H),3.63(s,0.24H),1.95(s,3H),1.83(s,0.24H)ppm.
2g of 13 The C NMR data are as follows: 13 C NMR(125MHz,CDCl 3 ):δ166.75,165.28,139.34,139.22,134.58,131.83,129.68,128.11,126.60,125.92,125.54,125.35,124.18,122.13,117.46,80.13,78.91,26.12,26.04,19.38,18.86ppm.
example 8
The reaction equation is as follows:
Figure BDA0004136750000000091
tetratriphenylphosphine palladium (2.5 mmol), R-BINAP (2.5 mmol), p-nitrophenol (50 mmol) and compound 1h (50 mmol) were added to the reactor under nitrogen, then 500mL of diethyl ether was added and stirred at 100deg.C for 18 hours to complete the reaction. And (3) performing column chromatography by using a mixed solvent with the volume ratio of petroleum ether to ethyl acetate being 50:1 to obtain pure 2h. The yield of 2h was 89%, E/z=4:1.
2h 1 The H NMR data are as follows: 1 H NMR(500MHz,CDCl 3 ):δ7.40(d,J＝7.6Hz,0.6H),7.36(s,1H),7.33(d,J＝7.8Hz,0.8H),7.30(d,J＝7.1Hz,3H),7.18(dd,J＝7.3,1.4Hz,2H),6.43(s,0.28H),5.21(s,1H),5.17(s,1H),5.15(s,0.28H),5.10(s,0.28H),2.00(s,0.84H),1.54(s,2.52H),1.46(s,9H),1.38(s,3H)ppm.
2h 13 The C NMR data are as follows: 13 C NMR(125MHz,CDCl 3 ):δ167.70,141.48,139.39,138.94,128.76,127.36,126.89,124.90,118.95,50.97,31.89,21.52ppm.
from the above examples, it can be seen that the method for synthesizing polysubstituted 1, 3-butadiene-based compounds according to the present invention can obtain diverse target products with high efficiency and high stereoselectivity.

Claims (5)

1. A synthetic method of polysubstituted 1, 3-butadiene compounds shown in formula I comprises the following steps: decarboxylation hydrogen transfer of GMDVs compound shown in formula (II) under the protection of nitrogen in the presence of tetraphenylphosphine palladium, phenols, R-BINAP and solvent,
Figure FDA0004136749990000011
wherein R is 1 Is one of methyl, ethyl and tert-butyl; r is R 2 Is one of methyl, benzyl, naphthyl, thienyl and substituted or unsubstituted phenyl, wherein the substituent is one of halogen atom, methyl, methoxy or phenyl and is positioned at the 2, 3 and 4 positions of the benzene ring.
2. The method according to claim 1, wherein the phenol is one of phenol, p-nitrophenol, p-methoxyphenol, p-methylphenol, and o-methylphenol.
3. The production method according to claim 1, wherein the amount of the tetraphenylphosphine palladium is 1 to 10mol parts and the amount of the phenol is 50 to 150mol parts, relative to 100 mol parts of the GMDVs-based compound; the amount of R-BINAP is 1 to 10 parts by mole.
4. The production process according to claim 1, wherein the decarboxylation hydrogen transfer reaction of the GMDVs-type compound is carried out at a temperature of 90 to 110 ℃ with stirring for 12 to 24 hours.
5. The preparation method according to claim 1, wherein column chromatography is performed with a mixed solvent of petroleum ether and ethyl acetate after the reaction.
CN202310277046.7A 2023-03-21 2023-03-21 Synthesis method of polysubstituted 1, 3-butadiene compound Pending CN116239471A (en)

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