CN110003147B - Preparation method of polysubstituted 3-benzylidene tetrahydrofuran compound - Google Patents
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Abstract
The invention provides a novel method for synthesizing a polysubstituted 3-benzylidene tetrahydrofuran compound by using cyclopropyl methanol and DMSO as raw materials under a milder reaction condition. The invention uses trifluoro methanesulfonic anhydride as catalyst under the reaction condition
As an oxidant and DMSO as a solvent, a polysubstituted 3-benzylidene tetrahydrofuran compound is synthesized by a one-pot method. The reaction utilizes cyclopropyl methanol and DMSO as substrates for the first time to synthesize the polysubstituted 3-benzylidene tetrahydrofuran compound, and the oxidant is
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of a polysubstituted 3-benzylidene tetrahydrofuran compound.
Background
The 3-benzylidene tetrahydrofuran is an important compound, is not only a core structural unit of a plurality of natural products, but also has biological activity, and has wide application in the aspects of medicine, pesticide, biochemistry, natural product synthesis, medicine synthesis, material chemistry and the like. 1 In addition, the 3-benzylidene tetrahydrofuran compound can also undergo substitution, oxidation, reduction, DA reaction, cycloaddition reaction and the like, and is an important intermediate for synthesizing heterocyclic compounds. It is therefore necessary to explore the synthesis of 3-benzylidene tetrahydrofuran compounds.
In recent years, the following methods have been exemplified for synthesizing 3-benzylidene tetrahydrofuran compounds:
(1) Beta-halogen alkynyl ether is used as a substrate:
in 1997, keiji Maruoka group reported that 2-iodoethyl-3-phenylpropynyl ether was subjected to intramolecular radical cycloaddition to produce 3-benzylidene tetrahydrofuran. 2 In this reaction, azoDiisobutyronitrile (AIBN) and tributylstannum hydrogen (Bu) 3 SnH) initiates cleavage of C-I bonds while new C-C bonds are formed. Wherein AIBN and Bu 3 SnH is the key of the reaction, and the configuration of the 3-benzylidene tetrahydrofuran derivative generated in the presence of the SnH and the benzylidene tetrahydrofuran derivative is Z/E, and the ratio of the SnH to the benzylidene tetrahydrofuran derivative is 50:50.
(2) 1, 6-eneyne is taken as a substrate:
in 2002, the Zhang Xumu subject group reported [ { Rh (cod) Cl } 2 ]Catalyzing the Alder-Ene reaction in the molecule of the eneyne to generate the 3-benzylidene tetrahydrofuran compound (formula 1). 3 Research has also found that in [ { Rh (cod) Cl }) 2 ]Under the combined action of BINAP, the yield of the 3-benzylidene tetrahydrofuran compound for generating chiral molecules is more than 99 percent. In addition, synthesis of other functionalized carbocyclic and heterocyclic compounds such as lactams and pyrrolidines is underway. In 2009, the Chirik group reported that iron catalyzes the reductive cyclization of 1, 6-eneyne to produce a 3-benzylidene tetrahydrofuran compound (equation 2). 4 The reaction starts from simple 1, 6-eneyne, forms diimine pyridine chelate through catalytic cyclization of iron-containing complex and single electron transfer and oxidation process, and then the formation of C-H bond and Fe-H bond in diimine pyridine chelate can be completed through oxidation addition/reduction elimination of hydrogen or sigma-bond exchange. Finally, the dihydro-cleavage forms the 3-benzylidene tetrahydrofuran derivative. In 2011, chung's group synthesized 3-benzylidene tetrahydrofuran compound (formula 3) using eneyne as a substrate. 5 During the reaction, the dinuclear complexes (dppp) are fragmented to form the monometal rhodium complexes. Subsequently, the alcohol is reacted with a catalyst monometallic rhodium complex and a complex unsaturated rhodium alkoxide compound is obtained. The alkoxide ligand then eliminates the beta-hydrogen and coordinates with the eneyne to produce a rhodium hydride compound. Finally, ethanol oxidizes the rhodium compound to produce the 3-benzylidene tetrahydrofuran derivative. In 2014, the Yang subject group found that the eneyne compound has intramolecular reductive cyclization under the catalysis of ferrous chloride, thereby constructing the chiral compound3-benzylidene tetrahydrofuran derivative (formula 4). 6 First, the lower-valence iron ions are generated under the combined action of ferrous chloride, magnesium bromide diethyl ether, ligand and diethyl zinc, and then the lower-valence iron ions and eneyne are oxidized and cyclized to form a metal cyclized compound. The cyclized compound breaks the metal bond under the action of diethyl zinc and reforms a compound containing two metal bonds. Finally, the 3-benzylidene tetrahydrofuran compound is formed by eliminating beta-hydrogen and decomposing protons.
(3) Allyl alcohol and vinyl ether are used as substrates:
in 2009, the Hosokawa group reported the use of the so-called Wacker catalyst PdX 2 ,CuX 2 (X＝OAc,OCOCF 3 Or Cl) and (S, S) -4,4' -benzyl bisoxazoline are used for catalyzing and inducing asymmetric coupling of cinnamyl alcohol and vinyl ether to obtain the reaction of 3-benzylidene tetrahydrofuran. 7 The activity of the catalytic system is increased during the reaction by adding catechol. Enantioselectivity to benzylidene tetrahydrofuran was determined from Pd (OAc) 2 And chiral ligands such as 5a, whereas reactivity is dependent on Cu (OAc) 2 And catechol.
(4) Epoxide is used as a substrate:
in 2001, the Alcaraz group reported the reaction of symmetrical glycidoxycarb compounds with thioylide to produce 3-benzylidene tetrahydrofuran derivatives. 8 In this reaction, sulfur ylide reacts with a glycidoxane compound as a nucleophile to form a betaine intermediate. Subsequently, betaine intermediates are subjected to intramolecular or intermolecular beta-elimination of dimethyl sulfide to give benzylidene tetrahydrofuran derivatives. Unfortunately, the above synthetic 3-benzylidene tetrahydrofuran derivatives are only one substrate of a broad range of reaction processes, and the synthesis is concernedCheng Yabian-base tetrahydrofuran derivatives are not systematically described.
(5) Alkene and ketone are used as substrates:
in 2013, the Bringley group of subjects reported a palladium catalyzed TMM with an aryl ketone [3+2]Cyclizing addition reaction to obtain 3-benzylidene tetrahydrofuran derivative. 9 In this reaction, the 3-benzylidene tetrahydrofuran derivative can be obtained by reacting the alpha, beta-unsaturated ketone as a substrate, and the substrate applicability of the reaction is proved to be good. The key factor in achieving this reaction is the use of C-1 symmetrical phosphoramides.
(6) Taking alkynol and diazodicarbonyl compound as substrates:
in 2014, the Hatakeyama group of topics reported Rh (II)/Zn (II) catalyzed propargyl alcohol and diazodicarbonyl compounds [4+1 ]]Cycloaddition reaction to produce 3-benzylidene tetrahydrofuran derivative. 10 In this reaction, rh 2 (esp) 2 Not participate in cyclization but in O-H insertion; znCl 2 In contrast, the cyclization reaction is promoted without participating in the O-H insertion reaction. The reaction substrate is well compatible and exhibits complete E-selectivity in the case of non-terminal alkynes.
(7) Taking alkynol and benzaldehyde as substrates:
in 1997, the Liu group reported the synthesis of 3-benzylidene tetrahydrofuran derivatives using propargyl tungsten compounds. 11 In this reaction, propargyl tungsten compound is reacted with benzaldehyde and boron trifluoride etherate in diethyl ether solution at-40℃to give pyrrolidinium ion. Along with itAfter that, the pyrrolidinium ion and NaBH 3 CN reacts in acetonitrile solution at-40 ℃ to obtain the 3-benzylidene tetrahydrofuran derivative.
Most of the above-mentioned synthetic 3-benzylidene tetrahydrofuran derivatives require noble metal catalysts such as gold, rhodium, etc.; or require complex ligands; or the reaction conditions are severe. Therefore, the cost for synthesizing the 3-benzylidene tetrahydrofuran derivative is high, and industrial application cannot be realized. There is a need to explore a simpler and more efficient method for synthesizing 3-benzylidene tetrahydrofuran derivatives.
The invention aims to solve the technical problems of harsh synthesis reaction conditions, complex reaction steps, high industrial cost and the like in the prior art, and provides a simple and efficient preparation method of a polysubstituted 3-benzylidene tetrahydrofuran derivative.
In order to solve the technical problems, the invention adopts the following technical scheme: sequentially adding a compound (1.0 equiv) with a general formula I, a solvent II,
(1.5equiv)、Tf 2 O (10 mol%) and air were placed in an oil bath at 170℃and reacted for 7.0h. Thin layer chromatography was used to monitor the progress of the reaction until it was complete. The organic layer was dried over anhydrous sodium sulfate, filtered, distilled under reduced pressure, and the concentrated solution was purified by column chromatography on silica gel with petroleum ether/ethyl acetate=40/1 mobile phase to give the compound and III according to the following reaction equation:
in the equation: r is R 1 Selected from phenyl, substituted phenyl, heterocyclic aromatic hydrocarbons, R 2 Selected from phenyl, alkyl.
The above description describes a process for the preparation of polysubstituted 3-benzylidene tetrahydrofuran compounds, characterized in that cyclopropyl methanol and DMSO are used as substrates for
As oxidant and trifluoro methanesulfonic anhydride as catalyst to perform oxidation serial cyclization reaction.
Compared with the prior art, the invention has the following advantages:
(1) The raw materials used in the invention are simple to prepare, low in cost and easy to obtain, and the 3-benzylidene tetrahydrofuran compound is synthesized by a one-pot method.
(2) The DMSO used in the invention is not only a substrate in the reaction process, but also a solvent in the reaction.
(3) The invention does not need expensive metal catalyst, and is safe to operate.
The technical scheme of the invention is further described in detail through examples.
Detailed Description
Example 1: the preparation method of the embodiment comprises the following steps:
into a 500mL round bottom flask was successively added compound Ia (100.6 g), DMSO (300 mL),
(834.7)、Tf 2 O (19.2 g) and air were placed in an oil bath at 170℃and the progress of the reaction was monitored by thin layer chromatography until the reaction was complete. The mixture was extracted with diethyl/brine, the organic layer was dried over anhydrous sodium sulfate, filtered, distilled under reduced pressure, and the concentrated solution was purified by silica gel column chromatography using a mobile phase of petroleum ether/ethyl acetate=40/1 to give compound IIIa in a yield of 72%. The reaction equation is as follows:
the structure, nuclear magnetism, and high resolution mass spectrum data of the product obtained in example 1 were as follows:
Yellow oil(72％yield),Z/E＝54:46. 1 H NMR(400MHz,CDCl 3 ,ppm):δ＝7.37-7.31(m,6H),7.22-7.21(m,2H),7.13-7.11(d,J＝7.4Hz,2H),6.45-6.44(t,J＝2.4Hz,Z isomer,1H),6.37-6.36(t,J＝2.2Hz,E isomer,1H),4.58(d,J＝1.8Hz,Z isomer,2H),4.45(d,J＝1.7Hz,E isomer,2H),4.02-3.99(t,J＝6.8Hz,E isomer,2H),3.91-3.88(t,J＝6.9Hz,Z isomer,2H),2.84-2.80(m,E isomer,2H),2.79-2.75(m,Z isomer,2H)； 13 C NMR(100MHz,CDCl 3 ,ppm):δ＝141.5,140.9,137.6,137.4,128.5,128.4,127.9,127.8,126.5,126.4,120.9,119.5,72.8,69.6,69.2,67.3,34.9,31.2；HRMS calcd for C 11 H 13 O[M+H] + 161.0961；found:161.0960.
examples 2 to 7 all the same reaction conditions except for the compounds of the general formula Ia used, specifically:
compound I (2-7) (100.6 g), DMSO (300 mL), a solution of the compound in DMSO (300 mL) and a solution of the compound in the compound were sequentially added to a 500mL round-bottomed flask,
(1.5equiv)、Tf 2 O (10 mol%) and air were placed in an oil bath at 170℃and the progress of the reaction was monitored by thin layer chromatography until the reaction was complete. Extracting with diethyl/saline solution, drying the organic layer with anhydrous sodium sulfate, filtering, distilling under reduced pressure, separating and purifying the concentrated solution by silica gel column chromatography with petroleum ether/ethyl acetate=40/1 mobile phase to obtain compound III (2-7) with a yield of 43% -73%. The reaction equation is as follows:
the structure, nuclear magnetism, and high resolution mass spectrum data of the product obtained in example 2 were as follows:
Yellow oil(70％yield),Z/E＝49:51. 1 H NMR(400MHz,CDCl 3 ,ppm):δ＝7.31-7.29(d,J＝7.2Hz,1H),7.20-7.11(m,6H),7.03-7.01(d,J＝7.2Hz,1H),6.54-6.53(t,J＝2.0Hz,Z isomer,1H),6.46-6.45(t,J＝2.0Hz,E isomer,1H),4.47-4.46(d,J＝1.6Hz,Z isomer,2H),4.45-4.44(d,J＝1.2Hz,E isomer,2H),3.96-3.93(t,J＝6.8Hz,E isomer,2H),3.93-3.89(t,J＝5.2Hz,Z isomer,2H),2.79-2.75(m,E isomer,2H),2.72-2.68(m,Z isomer,2H),2.30(s,Z isomer,3H),2.91(s,E isomer,3H)； 13 C NMR(100MHz,CDCl 3 ,ppm):δ＝141.5,141.3,136.5,136.4,136.0,135.7,130.0,129.9,127.7,127.4,126.8,126.7,125.8,125.6,119.0,117.6,72.3,69.3,69.0,67.4,34.2,30.8,20.0,19.9.HRMS calcd for C 12 H 15 O[M+H] + 175.1118；found:175.1116.
the structure, nuclear magnetism, and high resolution mass spectrum data of the product obtained in example 3 were as follows:
Yellow oil(70％yield),Z/E＝51:49. 1 H NMR(400MHz,CDCl 3 ,ppm):δ＝7.25-7.23(m,2H),7.18-7.16(m,4H),7.05-7.03(d,J＝8.4Hz,2H),6.42-6.41(t,J＝2.4Hz,Z isomer,1H),6.33-6.32(t,J＝2.0Hz,E isomer,1H),4.57-4.56(d,J＝1.6Hz,Z isomer,2H),4.44-4.43(d,J＝1.6Hz,E isomer,2H),4.01-3.97(t,J＝6.8Hz,E isomer,2H),3.90-3.86(t,J＝6.8Hz,Z isomer,2H),2.82-2.78(m,E isomer,2H),2.76-2.73(m,Z isomer,2H),2.67-2.60(m,Z and E isomer,4H),1.25-1.21(m,Z and E isomer,6H)； 13 C NMR(100MHz,CDCl 3 ,ppm):δ＝142.6,142.5,140.4,139.9,135.0,134.9,127.9,127.9,127.7,125.6,120.7,119.3,72.8,69.6,69.2,67.3,34.8,31.2,28.5,28.5,15.5,15.4；HRMS calcd for C 13 H 17 O[M+H] + 189.1274；found:189.1273.
the structure, nuclear magnetism, and high resolution mass spectrum data of the product obtained in example 4 were as follows:
Yellow oil(65％yield),Z/E＝52:48. 1 H NMR(400MHz,CDCl 3 ,ppm):δ＝7.35-7.33(m,1H),7.24-7.19(m,2H),7.03-7.01(m,1H),6.97-6.91(m,2H),6.89-6.86(m,2H),6.71-6.70(t,J＝2.4Hz,Z isomer,1H),6.63-6.62(t,J＝2.0Hz,E isomer,1H),4.51(t,J＝0.8Hz,Z isomer,2H),4.49-4.48(d,J＝1.6Hz,E isomer,2H),3.97-3.95(t,J＝6.8Hz,E isomer,2H),3.92-3.88(t,J＝6.8Hz,Z isomer,2H),3.84(d,J＝0.8Hz,Z and E isomer,6H),2.80-2.75(m,Z and E isomer,4H)； 13 C NMR(100MHz,CDCl 3 ,ppm):δ＝156.6,156.3,141.3,141.0,128.3,128.3,127.9,127.9,126.5,126.4,120.3,120.2,115.3,113.9,110.4,110.4,72.6,69.5,69.1,67.4,55.4,55.4,34.6,31.1；HRMS calcd for C 12 H 15 O 2 [M+H] + 191.1067；found:191.1068.
the structure, nuclear magnetism, and high resolution mass spectrum data of the product obtained in example 5 were as follows:
Yellow oil(41％yield),Z/E＝44:56. 1 H NMR(400MHz,CDCl 3 ,ppm):δ＝7.28-7.25(m,2H),7.09-7.00(m,6H),6.40-6.39(t,J＝2.4Hz,Z isomer,1H),6.32-6.31(d,J＝2.0Hz,E isomer,1H),4.53(d,J＝1.6Hz,Z isomer,2H),4.44-4.43(d,J＝2.0Hz,E isomer,2H),4.02-3.98(t,J＝6.8Hz,E isomer,2H),3.91-3.87(t,J＝7.2Hz,Z isomer,2H),2.78-2.73(m,Z and E isomer,4H)； 13 C NMR(100MHz,CDCl 3 ,ppm):δ＝161.3(d,J＝245.0Hz,1C),161.3(d,J＝245.0Hz,1C),141.1,140.5,133.7(d,J＝3.0Hz,1C),133.6(d,J＝3.0Hz,1C),129.4(d,J＝8.0Hz,1C),129.3-129.2(d,J＝8.0Hz,1C),119.8,118.3,115.3(d,J＝21.0Hz,1C),115.2(d,J＝21.0Hz,1C),72.7,69.4,69.1,67.3,34.7,31.1；HRMS calcd for C 11 H 12 FO[M+H] + 179.1867；found:179.1869.
the structure, nuclear magnetism, and high resolution mass spectrum data of the product obtained in example 6 were as follows:
Yellow oil(45％yield),Z/E＝53:47. 1 H NMR(400MHz,CDCl 3 ,ppm):δ＝7.47-7.41(m,4H),7.19-7.17(d,J＝8.4Hz,E isomer,2H),6.99-6.97(d,J＝8.4Hz,2H),6.39-6.37(t,J＝2.4Hz,Z isomer,1H),6.30-6.29(t,J＝2.0Hz,E isomer,1H),4.53(d,J＝1.6Hz,Z isomer,2H),4.44-4.43(d,J＝1.6Hz,E isomer,2H),4.03-3.99(t,J＝6.8Hz,E isomer,2H),3.92-3.89(t,J＝6.8Hz,Z isomer,2H),2.79-2.74(m,Z and E isomer,4H)； 13 C NMR(100MHz,CDCl 3 ,ppm):δ＝142.5,142.0,136.4,136.3,131.6,131.5,129.5,129.3,120.3,119.9,118.4,72.9,69.5,69.2,67.3,34.9,31.2；HRMS calcd for C 11 H 12 BrO[M+H] + 239.0066；found:239.0063.
the structure, nuclear magnetism, and high resolution mass spectrum data of the product obtained in example 7 were as follows:
Yellow oil(73％yield),Z/E＝49:51. 1 H NMR(400MHz,CDCl 3 ,ppm):δ＝7.36-7.30(m,4H),7.27-7.22(m,4H),7.17-7.15(m,2H),4.43-4.42(d,J＝1.6Hz,Z isomer,2H),4.24-4.23(m,E isomer,2H),3.97-3.94(t,J＝6.8Hz,E isomer,2H),3.87-3.84(t,J＝6.8Hz,Z isomer,2H),2.64-2.61(m,E isomer,2H),2.55-2.51(m,Z isomer,2H),2.06-2.04(m,E isomer,3H),1.96-1.95(m,Z isomer,3H)； 13 C NMR(100MHz,CDCl 3 ,ppm):δ＝143.5,143.3,135.8,135.7,128.2,128.1,127.3,127.0,126.8,126.5,126.4,126.0,70.6,70.4,69.2,68.3,32.1,31.5,21.3,20.4；HRMS calcd for C 12 H 15 O[M+H] + 175.1117；found:175.1115.
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Claims (1)
1. a process for the preparation of a polysubstituted 3-benzylidene tetrahydrofuran compound comprising the steps of: sequentially adding 1.0equiv of the general formula compound I, the compound II and 2.0 equiv into a reactor
10mol% of trifluoromethanesulfonic anhydride is placed in an oil bath at 170 ℃ under the air condition for reaction for 7.0h, the reaction progress is monitored by thin layer chromatography until the reaction is complete, ethyl acetate/saline solution is used for extraction, an organic layer is dried by anhydrous sodium sulfate, filtration and reduced pressure distillation, a concentrated solution is separated and purified by silica gel column chromatography by taking petroleum ether/ethyl acetate=40/1 as a mobile phase, and the compound III is obtained, wherein the reaction equation is as follows:
in the equation: r is R 1 Selected from hydrogen, methyl, ethyl, methoxy, fluoro, bromo; r is R 2 Selected from hydrogen, methyl;
the compound II is DMSO, which is both a substrate and a solvent in the reaction, the
As an oxidizing agent, the trifluoromethanesulfonic anhydride acts as a catalyst. />
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