CN101250170A - Method for synthesizing 4-(1', 3'-conjugated diene-2'-group)-2,5-dihydrofuran - Google Patents

Method for synthesizing 4-(1', 3'-conjugated diene-2'-group)-2,5-dihydrofuran Download PDF

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CN101250170A
CN101250170A CNA2008100605583A CN200810060558A CN101250170A CN 101250170 A CN101250170 A CN 101250170A CN A2008100605583 A CNA2008100605583 A CN A2008100605583A CN 200810060558 A CN200810060558 A CN 200810060558A CN 101250170 A CN101250170 A CN 101250170A
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dihydrofuran
replacement
enol
dmso
boron trifluoride
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CN101250170B (en
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麻生明
邓友前
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Zhejiang University ZJU
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Zhejiang University ZJU
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Abstract

The invention relates to a method for synthesizing 4-(1', 3'-conjugated diene-2'-group)-2, 5-dihydrofuran with high stereoselectivity, wherein in the catalysis of palladium iodide and the presence of one equivalent of boron trifluoride diethyl etherate, one molecule of 2, 3-allenol whose two elements are substituted and one molecule of 2, 3-allenol whose two elements are not substituted are reacted via cross coupling to synthesize 4-(1', 3'-conjugated diene-2'-group)-2, 5-dihydrofuran, the invention has simple operation, easily accessible materials and agents, high reaction stereoselectivity and the ability for leading a plurality of substituents at same time, and the product is easily to be separated and purified. The invention is suitable for synthesizing various substituted 4-(1', 3'-conjugated diene-2'-group)-2, 5-dihydrofuran.

Description

Synthetic 4-(1 ＇, 3 ＇-conjugated diolefine-2 ＇-yl)-2, the method for 5-dihydrofuran
Technical field
The present invention relates to a kind of highly-solid selectively ground and synthesize 4-(1 ', 3 '-conjugated diolefine-2 '-yl)-2, the method for 5-dihydrofuran.
Background technology
2,5-dihydrofuran and 1,3-conjugated diolefine structure all is an intermediate important in the organic synthesis, it also is modal structural unit in the natural product, have multiple important physical activity, at biological technical field, there is huge value of exploiting and utilizing aspects such as medicine and agricultural chemicals.Bibliographical information about containing 1,2 of 3-conjugated diolefine structure, the reaction yield of 5-dihydrofuran synthetic method lower (Ma, S. in the past; Gao, W.J.Org.Chem.2002,67,6104; Hashmi, A.S.K.; Carmen Blanco, M.; Fischer, D.; Bats, J.W.Eur.J.Org.Chem.2006,1387.), and structure substituting group more single (Deng, Y.; Yu, Y.; Ma, S.J.Org.Chem.2008,73,585).
Therefore (1 ', 3 '-conjugated diolefine-2 '-yl)-2, the 5-dihydrofuran is the very quantum jump that reacts in the past to the various 4-of effectively convenient synthetic highly-solid selectively and substituting group.
Summary of the invention
Purpose of the present invention just provide a kind of at palladium iodide catalysis and the effect of an equivalent boron trifluoride diethyl etherate under 2 of a part 2 of replacement is arranged, 2 of 3-connection enol and another molecules do not have 2 of replacement, intermolecular cross-coupling reaction takes place in 3-connection enol, highly-solid selectively ground synthesizes the various 4-of substituting group (1 ', 3 '-conjugated diolefine-2 '-yl)-2, the method for 5-dihydrofuran.
The present invention synthesizes 4-(1 ', 3 '-conjugated diolefine-2 '-yl)-2, the method of 5-dihydrofuran, promptly by under the effect of the catalysis of palladium iodide and an equivalent boron trifluoride diethyl etherate, 2 of a part have 2 of replacement, 2 of 3-connection enol and another molecules do not have 2 of replacement, intermolecular cross-coupling reaction takes place in 3-connection enol, and highly-solid selectively ground synthesizes the various 4-of substituting group (1 ', 3 '-conjugated diolefine-2 '-yl)-2, the 5-dihydrofuran, reaction formula is as follows:
Figure S2008100605583D00011
R 1=alkyl, phenyl, allyl group, ester group; R 2=alkyl, aryl; R 3=alkyl, phenyl the steps include:
(1) at room temperature, getting 2 of raw materials has 2 of replacement, 3-connection enol, palladium iodide, organic solvent dimethyl sulfoxide (DMSO), boron trifluoride diethyl etherate, 2 do not replace 2,3-joins enol; By 22 of replacement is arranged, 3-connection enol and palladium iodide, dimethyl sulfoxide (DMSO), 2 do not replace 2, the mol ratio that 3-joins between enol and the equivalent boron trifluoride diethyl etherate is respectively: 1: 0.05; 0.98～1.09mmol/5mL; 1: 1.1～1.3; 1: 0.98～1.09 ratio is reinforced, order is: past 2 do not have 2 of replacement, add the organic solvent dimethyl sulfoxide (DMSO) of half in 3-connection enol and the palladium iodide mixture successively, an equivalent boron trifluoride diethyl etherate, 2 have 2 of replacement, 3-connection enol and second half organic solvent dimethyl sulfoxide (DMSO);
(2), be as cold as room temperature and add shrend and go out extracted with diethyl ether 80 ℃ of heated and stirred reaction 0.5～1.5 hour;
(3) concentrate, rapid column chromatography, acquisition 4-(1 ', 3 '-conjugated diolefine-2 '-yl)-2, the 5-dihydrofuran.
Of the present invention 2 not do not replace 2,3-connection enol and 2 have 2 of replacement, the mol ratio of 3-connection enol is: 1.1-1.3/1 is preferably 1.1: 1.
Organic solvent of the present invention is the non-protonic solvent dimethyl sulfoxide (DMSO).2 have 2 of replacement, and 3-connection enol and dimethyl sulfoxide (DMSO) mol ratio are: 0.98-1.09mmol/5mL is preferably 1mmol/5mL.
Palladium iodide of the present invention and 2 have 2 of replacement, and the mol ratio of 3-connection enol is 0.05: 1.
Boron trifluoride diethyl etherate of the present invention and 2 have 2 of replacement, and the mol ratio of 3-connection enol is 0.98-1.09: 1, be preferably 1: 1.
The present invention relates to a kind ofly has 2 of replacement by 2 of a part, 2 of 3-connection enol and another molecules do not have 2 of replacement, 3-connection enol is under the effect of the catalysis of palladium iodide and an equivalent boron trifluoride diethyl etherate, intermolecular cross-coupling reaction takes place, highly-solid selectively ground synthesizes 4-(1 ', 3 '-conjugated diolefine-2 '-yl)-2, the method for 5-dihydrofuran.Simple to operate, raw material and reagent are easy to get, and reaction has the stereoselectivity of height, are applicable to 4-(1 ', 3 '-conjugated diolefine-2 '-yl)-2, the 5-dihydrofuran of synthetic various replacements.
The present invention has overcome the drawback of traditional method, has the following advantages: 1) reaction has the stereoselectivity of height; 2) easy to operate, the productive rate height; 3) the easily separated purifying of product.
Innovative point of the present invention has been to develop a kind of highly-solid selectively ground and has synthesized the various 4-of substituting group (1 ', 3 '-conjugated diolefine-2 '-yl)-2, the methodology of 5-dihydrofuran.
(1 ', 3 '-conjugated diolefine-2 '-yl)-2, the productive rate of 5-dihydrofuran is 38-81% to the corresponding 4-of gained of the present invention.
Embodiment
Following examples help to understand the present invention, but are not limited to content of the present invention.
Embodiment 1
Add under the room temperature palladium iodide (18.5mg, 0.051mmol), 2,3-divinyl-1-alcohol (77.9mg, 1.11mmol), dimethyl sulfoxide (DMSO) (2.5mL), boron trifluoride diethyl etherate (127 μ L, 1mmol), 4-normal-butyl-4,5-hexadiene-3-alcohol (154.7mg, 1mmol), and dimethyl sulfoxide (DMSO) (2.5mL), put 80 ℃ then and reacted completely in following 1.5 hours, be chilled to room temperature, add the 10mL shrend and go out, extracted with diethyl ether (3 * 25mL), saturated Na 2S 2O 3The aqueous solution, saturated aqueous common salt are respectively washed once, and anhydrous sodium sulfate drying filters, and concentrate, and rapid column chromatography gets product 2-ethyl-3-normal-butyl-4-(1 '-methylene radical-2 '-propenyl)-2, and 5-dihydrofuran 118.6mg, productive rate are 57%.Product is a colourless liquid.
1H?NMR(400MHz，CDCl 3)δ6.37(dd，J 1＝17.6Hz，J 2＝10.4Hz，1H)，5.23(s，1H)，5.17(d，J＝17.6Hz，1H)，5.10(d，J＝10.4Hz，1H)，4.98(s，1H)，4.92-4.84(m，1H)，4.67-4.55(m，2H)，2.24-2.12(m，1H)，1.88-1.70(m，2H)，1.59-1.46(m，1H)，1.44-1.16(m，4H)，0.93(t，J＝7.2Hz，3H)，0.85(t，J＝6.8Hz，3H)； 13C?NMR(100MHz，CDCl 3)δ?141.2，137.6，137.2，131.0，117.8，116.1，88.3，77.6，29.9，26.8，?25.3，22.6，13.8，?8.5；IR(neat，cm -1)：3089，?2960，2932，2873，2859，1825，1585，1456，1379，1355，1030，899；MS(m/z)：206(M +，2.85)，177(M +-C 2H 5，27.81)，57(100)；HRMS?calcd?for?C 14H 22O(M +)：206.1671；found：206.1666.
Embodiment 2
Press embodiment 1 described method, different is that used substrate and reagent are: and palladium iodide (18.2mg, 0.050mmol), 2, and 3-divinyl-1-alcohol (80.2mg, 1.15mmol), boron trifluoride diethyl etherate (127 μ L, 1mmol), 3-normal-butyl-3,4-pentadiene-2-alcohol (137.7mg, 0.98mmol), and dimethyl sulfoxide (DMSO) (5mL) product 2-methyl-3-normal-butyl-4-(1 '-methylene radical-2 '-propenyl)-2,5-dihydrofuran 115.6mg, productive rate are 61%.Product is a colourless liquid.
1H?NMR(400MHz，CDCl 3)δ6.37(dd，J 1＝17.6Hz，J 2＝10.4Hz，1H)，5.24(s，1H)，5.17(d，J＝17.6Hz，1H)，5.10(d，J＝10.4Hz，1H)，4.98-4.89(m，2H)，4.68-4.52(m，2H)，2.24-2.11(m，1H)，1.96-1.84(m，1H)，1.45-1.18(m，7H)，0.86(t，J＝6.8Hz，3H)； 13C?NMR(100MHz，CDCl 3)δ141.1，139.7，137.1，130.0，117.8，116.0，83.8，76.9，29.8，25.2，22.6，20.6，13.8；IR(neat，cm -1)：3089，2960，2930，2859，1585，1457，1366，1338，1063，1019，913；MS(m/z)：192(M +，3.99)，177(M +-CH 3，11.50)，43(100)；HRMS?calcd?for?C 13H 20O(M +)：192.1514；found：192.1509.
Embodiment 3
Press embodiment 1 described method, different is that used substrate and reagent are: and palladium iodide (18.2mg, 0.050mmol), 2, and 3-divinyl-1-alcohol (86.4mg, 1.23mmol), boron trifluoride diethyl etherate (127 μ L, 1mmol), 1-phenyl-2-normal-butyl-2,3-divinyl-1-alcohol (220.4mg, 1.09mmol), and dimethyl sulfoxide (DMSO) (5mL) product 2-phenyl-3-normal-butyl-4-(1 '-methylene radical-2 '-propenyl)-2,5-dihydrofuran 215.8mg, productive rate are 78%.Product is a colourless liquid.
1H?NMR(400MHz，CDCl 3)δ7.43-7.29(m，5H)，6?.45(dd，J 1＝17.6Hz，J 2＝10.4Hz，1H)，5.82-5.75(m，1H)，5.33(s，1H)，5.29(d，J＝17.6Hz，1H)，5.18(d，J＝10.4Hz，1H)，5.11(s，1H)，4.93(ddd，J 1＝11.6Hz，J 2＝5.2Hz，J 3＝2.0Hz，1H)，4.82(dd，J 1＝11.6Hz，J 2＝2.0Hz，1H)，2.22-2.07(m，1H)，1.72-1.58(m，1H)，1.42-1.10(m，4H)，0.82(t，J＝6.8Hz，3H)； 13C?NMR(100MHz，CDCl 3)δ141.7，140.8，138.7，137.1，131.1，128.5，127.9，127.0，118.2，116.3，90.7，78.3，29.8，25.2，22.5，13.7；IR(neat，cm -1)：3086，3029，2957，2931，2858，1585，1492，1455，1050，1027，904；MS(m/z)：254(M +，2.02)，197(M +-C 4H 9，87.71)，105(100)；HRMS?calcd?for?C 18H 22O(M +)：254.1671；found：254.1661.
Embodiment 4
Press embodiment 1 described method, different is that used substrate and reagent are: and palladium iodide (18.0mg, 0.050mmol), 2, and 3-divinyl-1-alcohol (79.4mg, 1.13mmol), boron trifluoride diethyl etherate (127 μ L, 1mmol), 3-phenyl-1,2-octadiene-4-alcohol (203.0mg, 1.00mmol), and dimethyl sulfoxide (DMSO) (5mL) product 2-normal-butyl-3-phenyl-4-(1 '-methylene radical-2 '-propenyl)-2,5-dihydrofuran 179.7mg, productive rate are 70%.Product is a colourless liquid.
1H?NMR(400MHz，CDCl 3)δ7.26-7.10(m，5H)，6.23(dd，J 1＝17.6Hz，J 2＝10.4Hz，1H)，5.40-5.30(m，1H)，5.18(s，1H)，5.14(d，J＝17.6Hz，1H)，4.98(d，J＝10.4Hz，1H)，4.97(s，1H)，4.85(dd，J 1＝12.8Hz，J 2＝5.6Hz，1H)，4.63(dd，J 1＝12.8Hz，J 2＝2.8Hz，1H)，1.66-1.54(m，1H)，1.52-1.39(m，1H)，1.38-1.28(m，2H)，1.26-1.10(m，2H)，0.77(t，J＝7.2Hz，3H)； 13C?NMR(100MHz，CDCl 3)δ141.2，137.2，136.5，133.8，132.7，128.1，127.7，127.3，118.4，116.4，88.7，78.9，34.2，27.0，22.7，14.0；IR(neat，cm -1)：3087，3057，3029，2956，2931，2858，1811，1585，1496，1466，1350，1054，904；MS(m/z)：254(M +，16.43)，197(M +-C 4H 9，60.11)，169(M +-C 4H 9CO，87.80)，91(100)；HRMS?calcd?for?C 18H 22O(M +)：254.1671；found：254.1674.
Embodiment 5
Press embodiment 1 described method, different is that used substrate and reagent are: and palladium iodide (18.0mg, 0.050mmol), 2, and 3-divinyl-1-alcohol (81.6mg, 1.17mmol), boron trifluoride diethyl etherate (127 μ L, 1mmol), 3-allyl group-3,4-pentadiene-2-alcohol (124.7mg, 1.01mmol), and dimethyl sulfoxide (DMSO) (5mL) product 2-methyl-3-allyl group-4-(1 '-methylene radical-2 '-propenyl)-2,5-dihydrofuran 86.8mg, productive rate are 49%.Product is a colourless liquid.
1H?NMR(400MHz，CDCl 3)δ6.36(dd，J 1＝17.6Hz，J 2＝10.8Hz，1H)，5.73-5.60(m，1H)，5.24(s，1H)，5.17(d，J＝17.6Hz，1H)，5.10(d，J＝10.8Hz，1H)，5.05-4.96(m，3H)，4.95-4.85(m，1H)，4.67(ddd，J 1＝11.6Hz，J 2＝4.8Hz，J 3＝2.4Hz，1H)，4.63-4.54(m，1H)，2.94(dd，J 1＝15.6Hz，J 2＝6.0Hz，1H)，2.65(dd，J 1＝15.6Hz，J 2＝7.2Hz，1H)，1.28(d，J＝6.4Hz，3H)； 13C?NMR(100MHz，CDCl 3)δ140.6，137.1，137.0，134.8，131.3，117.9，116.2，83.8，76.7，30.1，20.5；IR(neat，cm -1)：3087，3006，2972，2925，2841，1830，1637，1584，1429，1367，1342，1300，1247，1070，1018，990，913，871；MS(m/z)：176(M +，2.66)，161( +-CH 3，17.13)，43(100)；HRMS?calcd?for?C 12H 16O(M +)：176.1201；found：176.1199.
Embodiment 6
Press embodiment 1 described method, different is that used substrate and reagent are: and palladium iodide (18.0mg, 0.050mmol), 2, and 3-divinyl-1-alcohol (84.1mg, 1.20mmol), boron trifluoride diethyl etherate (127 μ L, 1mmol), 1-p-methylphenyl-2-ester group-2,3-divinyl-1-alcohol (218.1mg, 1.00mmol), and dimethyl sulfoxide (DMSO) (5mL) product 2-p-methylphenyl-3-ester group-4-(1 '-methylene radical-2 '-propenyl)-2,5-dihydrofuran 147.4mg, productive rate are 55%.Product is a colourless liquid.
1H?NMR(400MHz，CDCl 3)δ7.29(d，J＝8.0Hz，2H)，7.18(d，J＝8.0Hz，2H)，6.48(dd，J 1＝17.6Hz，J 2＝10.8Hz，1H)，6.09(dd，J 1＝6.0Hz，J 2＝2.8Hz，1H)，5.40(s，1H)，5.26(d，J＝17.6Hz，1H)，5.21(d，J＝10.8Hz，1H)，5.20(s，1H)，5.05(dd，J 1＝14.8Hz，J 2＝6.0Hz，1H)，4.87(dd，J 1＝14.8Hz，J 2＝2.8Hz，1H)，3.56(s，3H)，2.36(s，3H)； 13C?NMR(100MHz，CDCl 3)δ162.8，148.4，139.6，137.90，137.87，135.9，130.2，129.0，126.9，117.8，116.0，88.9，79.1，51.3，21.1；IR(neat，cm -1)：3091，2950，2846，1724，1668，1620，1585，1514，1436，1358，1301，1251，1151，1097，1060，1021，907，810；MS(m/z)：270(M +，24.28)，238(M +-CH 3OH，9.62)，211(M +-CO 2CH 3，50.38)，119(100)；HRMS?calcd?for?C 17H 18O 3(M +)：270.1256；found：270.1254.
Embodiment 7
Press embodiment 1 described method, different is that used substrate and reagent are: and palladium iodide (18.1mg, 0.050mmol), 2, and 3-divinyl-1-alcohol (77.3mg, 1.10mmol), boron trifluoride diethyl etherate (127 μ L, 1mmol), 1-p-nitrophenyl-2-normal-butyl-2,3-divinyl-1-alcohol (247.1mg, 1.0mmol), and dimethyl sulfoxide (DMSO) (5mL) product 2-p-nitrophenyl-3-normal-butyl-4-(1 '-methylene radical-2 '-propenyl)-2,5-dihydrofuran 208.6mg, productive rate are 70%.Product is a colourless liquid.
1H?NMR(300MHz，CDCl 3)δ8.23(d，J＝8.7Hz，2H)，7.49(d，J＝8.7Hz，2H)，6.41(dd，J 1＝17.4Hz，J 2＝10.5Hz，1H)，5.88-5.77(m，1H)，5.32(s，1H)，5.18(d，J＝17.4Hz，1H)，5.15(d，J＝10.5Hz，1H)，5.08(s，1H)，4.93(ddd，J 1＝12.0Hz，J 2＝5.7Hz，J 3＝2.4Hz，1H)，4.83(dd，J 1＝12.0Hz，J 2＝2.4Hz，1H)，2.20-2.00(m，1H)，1.65-1.46(m，1H)，1.45-1.05(m，4H)，0.80(t，J＝7.2Hz，3H)； 13C?NMR(75MHz，CDCl 3)δ149.4，147.6，140.2，137.8，136.9，132.1，127.6，123.8，118.6，116.3，89.5，78.7，29.8，25.0，22.4，13.7；IR(neat，cm -1)：2957，2931，2858，1606，1525，1466，1348，1272，1228，1107，1053，1014，908，853，826，750；MS(m/z)：299(M +，1.68)，242(M +-C 4H 9，100)；HRMS?calcd?for?C 18H 21NO 3(M +)：299.1521；found：299.1511.
Embodiment 8
Press embodiment 1 described method, different is that used substrate and reagent are: palladium iodide (7.3mg, 0.020mmol), 3-ethyl-4,5-hexadiene-3-alcohol (68.4mg, 0.54mmol), boron trifluoride diethyl etherate (51 μ L, 0.4mmol), 1-p-nitrophenyl-2-normal-butyl-2,3-divinyl-1-alcohol (96.6mg, 0.39mmol), and dimethyl sulfoxide (DMSO) (2mL) product 2-p-nitrophenyl-3-normal-butyl-4-(1 '-methylene radical-3 '-ethyl-2 '-pentenyl)-2,5-dihydrofuran 69.0mg, productive rate are 50%.Product is a colourless liquid.
1H?NMR(300MHz，CDCl 3)δ8.21(d，J＝8.4Hz，2H)，7.45(d，J＝8.4Hz，2H)，5.81-5.72(bs，2H)，5.08-4.75(m，4H)，2.50-2.34(m，1H)，2.20(q，J＝7.5Hz，2H)，2.10(q，J＝7.5Hz，2H)，1.70-1.50(m，1H)，1.40-1.06(m，4H)，1.03(t，J＝7.5Hz，3H)，0.98(t，J＝7.5Hz，3H)，0.80(t，J＝7.2Hz，3H)； 13C?NMR(75MHz，CDCl 3)δ149.4，147.6，146.5，138.5，137.3，132.9，127.8，123.7，122.6，116.6，90.5，78.0，30.5，28.6，25.3，23.9，22.7，13.7，13.2，12.3；IR(neat，cm -1)：2963，2932，2858，1642，1603，1525，1461，1347，1263，1107，1051，1014，962，897，857，830，751；MS(m/z)：355(M +，3.40)，326(M +-C 2H 5，100)；HRMS?calcd?for?C 22H 29NO 3(M +)：355.2147；found：355.2153.
Embodiment 9
Press embodiment 1 described method, different is that used substrate and reagent are: palladium iodide (7.3mg, 0.020mmol), 1-(1 ', 2 '-propadiene base) hexalin (75.3mg, 0.55mmol), boron trifluoride diethyl etherate (51 μ L, 0.4mmol), 1-p-nitrophenyl-2-normal-butyl-2,3-divinyl-1-alcohol (99.9mg, 0.40mmol), and dimethyl sulfoxide (DMSO) (2mL) product 2-p-nitrophenyl-3-normal-butyl-4-(1 '-cyclohexylidene methyl ethylene)-2,5-dihydrofuran 85.3mg, productive rate are 57%.Product is a colourless liquid.
1H?NMR(300MHz，CDCl 3)δ8.21(d，J＝8.7Hz，2H)，7.45(d，J＝8.7Hz，2H)，5.80-5.72(m，2H)，5.08-5.01(m，2H)，4.99(ddd，J 1＝11.7Hz，J 2＝5.1Hz，J 3＝1.8Hz，1H)，4.83(dd，J 1＝11.7Hz，J 2＝3.0Hz，1H)，2.50-2.34(m，1H)，2.33-2.22(m，2H)，2.20-2.08(m，2H)，1.70-1.43(m，7H)，1.42-1.04(m，4H)，0.81(t，J＝7.2Hz，3H)； 13C?NMR(75MHz，CDCl 3)δ149.5，147.6，143.6，138.0，137.1，133.2，127.8，123.7，121.5，117.1，90.4，78.1，37.3，30.5，29.6，28.3，27.8，26.6，25.2，22.7，13.7；IR(neat，cm -1)：2955，2928，2855，1645，1607，1525，1447，1347，1264，1232，1107，1051，1014，898，855，829，750；MS(m/z)：367(M +，32.61)，41(100)；HRMS?calcd?for?C 23H 29NO 3(M +)：367.2147；found：367.2135.
Embodiment 10
Press embodiment 1 described method, different is that used substrate and reagent are: and palladium iodide (7.3mg, 0.020mmol), 1-phenyl-3, and 4-pentadiene-2-alcohol (84.6mg, 0.53mmol), boron trifluoride diethyl etherate (51 μ L, 0.4mmol), 3-normal-butyl-3,4-pentadiene-2-alcohol (55.9mg, 0.40mmol), and dimethyl sulfoxide (DMSO) (2mL) product 2-methyl-3-normal-butyl-4-(1 '-methylene radical-4 '-phenyl-2 '-butenyl)-2,5-dihydrofuran 61.5mg, productive rate are 55%.Product is a colourless liquid.
1H?NMR(300MHz，CDCl 3)δ7.24-7.04(m，5H)，6.06(d，J＝15.6Hz，1H)，5.72(dt，J 1＝15.6Hz，J 2＝6.9Hz，1H)，5.09(s，1H)，4.90-4.78(m，1H)，4.82(s，1H)，4.62-4.45(m，2H)，3.35(d，J＝6.9Hz，2H)，2.20-2.01(m，1H)，1.90-1.70(m，1H)，1.40-1.05(m，7H)，0.76(t，J＝6.6Hz，3H)； 13CNMR(75MHz，CDCl 3)δ140.6，139.9，139.3，131.7，131.4，130.7，128.5，128.4，126.1，116.1，83.9，77.0，38.9，29.9，25.3，22.7，20.6，13.8；IR(neat，cm -1)：2959，2929，2859，1641，1602，1495，1453，1367，1338，1060，1017，968，890，852，748，699；MS(m/z)：282(M +，1.49)，267(M +-CH 3，6.61)，239(M +-C 3H 7，58.14)，91(100)；HRMS?calcd?for?C 20H 26O(M +)：282.1984；found：282.1989.
Embodiment 11
Press embodiment 1 described method, different is that used substrate and reagent are: and palladium iodide (7.4mg, 0.020mmol), 1-phenyl-3, and 4-pentadiene-2-alcohol (72.9mg, 0.46mmol), boron trifluoride diethyl etherate (51 μ L, 0.4mmol), 1-phenyl-2-normal-butyl-2,3-divinyl-1-alcohol (80.0mg, 0.40mmol), and dimethyl sulfoxide (DMSO) (2mL) product 2-phenyl-3-normal-butyl-4-(1 '-methylene radical-4 '-phenyl-2 '-butenyl)-2,5-dihydrofuran 84.7mg, productive rate are 62%.Product is a colourless liquid.
1H?NMR(300MHz，CDCl 3)δ7.40-7.12(m，10H)，6.17(d，J＝15.6Hz，1H)，5.89(dt，J 1＝15.6Hz，J 2＝6.6Hz，1H)，5.78-5.66(m，1H)，5.22(s，1H)，4.98(s，1H)，4.88(ddd，J 1＝11.7Hz，J 2＝5.4Hz，J 3＝2.1Hz，1H)，4.78(dd，J 1＝11.7Hz，J 2＝2.1Hz，1H)，3.51(d，J＝6.6Hz，2H)，2.20-2.02(m，1H)，1.66-1.50(m，1H)，1.40-1.00(m，4H)，0.76(t，J＝6.6Hz，3H)； 13C?NMR(75MHz，CDCl 3)δ141.7，140.3，139.9，138.3，131.9，131.7，131.6，128.5，128.4，128.0，127.0，126.1，116.5，90.7，78.4，38.8，29.8，25.3，22.5，13.8；IR(neat，cm -1)：2956，2930，2858，1641，1602，1494，1454，1046，1028，969，894，753，699；MS(m/z)：344(M +，0.92)，105(100)；HRMS?calcd?forC 25H 28O(M +)：344.2140；found：344.2131.
Embodiment 12
Press embodiment 1 described method, different is that used substrate and reagent are: and palladium iodide (7.2mg, 0.020mmol), 1, and 2-decadiene-4-alcohol (68.0mg, 0.44mmol), boron trifluoride diethyl etherate (51 μ L, 0.4mmol), 1-p-nitrophenyl-2-normal-butyl-2,3-divinyl-1-alcohol (99.9mg, 0.40mmol), and dimethyl sulfoxide (DMSO) (2mL) product 2-p-nitrophenyl-3-normal-butyl-4-(1 '-methylene radical-2 '-nonene base)-2,5-dihydrofuran 106.9mg, productive rate are 69%.Product is a colourless liquid.
1H?NMR(300MHz，CDCl 3)δ8.23(d，J＝8.4Hz，2H)，7.48(d，J＝8.4Hz，2H)，6.09(d，J＝15.6Hz，1H)，5.86-5.76(m，1H)，5.65(dt，J 1＝15.6Hz，J 2＝6.9Hz，1H)，5.18(s，1H)，4.97-4.75(m，3H)，2.20-2.00(m，3H)，1.64-1.46(m，1H)，1.45-1.08(m，12H)，0.87(t，J＝6.9Hz，3H)，0.80(t，J＝6.6Hz，3H)； 13C?NMR(75MHz，CDCl 3)δ?149.5，147.6，140.0，137.1，133.8，133.1，130.1，127.6，123.8，115.9，89.5，78.9，32.5，31.6，29.9，29.1，28.8，25.0，22.6，22.5，14.0，13.7；IR(neat，cm -1)：2957，2928，2856，1792，1642，1607，1525，1466，1347，1272，1228，1107，1051，1014，967，893，855，829，751；MS(m/z)：383(M +，4.17)，354(M +-C 2H 5，3.80)，326(M +-C 4H 9，29.17)，233(100)；HRMS?calcd?for?C 24H 33NO 3(M +)：383.2460；found：383.2453.
Embodiment 13
Press embodiment 1 described method, different is that used substrate and reagent are: palladium iodide (7.3mg, 0.020mmol), 1-phenyl-3,4-pentadiene-2-alcohol (72.4mg, 0.45mmol), boron trifluoride diethyl etherate (51 μ L, 0.4mmol), 1-p-nitrophenyl-2-normal-butyl-2,3-divinyl-1-alcohol (98.9mg, 0.40mmol), and dimethyl sulfoxide (DMSO) (2mL) product 2-p-nitrophenyl-3-normal-butyl-4-(1 '-methylene radical-4 '-phenyl-2 '-butenyl)-2,5-dihydrofuran 126.3mg, productive rate are 81%.Product is a colourless liquid.
1H?NMR(300MHz，CDCl 3)δ8.19(d，J＝8.4Hz，2H)，7.44(d，J＝8.4Hz，2H)，7.30(t，J＝7.5Hz，2H)，7.22(d，J＝7.5Hz，1H)，7.16(d，J＝7.5Hz，2H)，6.17(d，J＝15.6Hz，1H)，5.88-5.73(m，2H)，5.24(s，1H)，4.98(s，1H)，4.98-4.76(m，2H)，3.45(d，J＝6.9Hz，2H)，2.20-2.00(m，1H)，1.60-1.44(m，1H)，1.40-1.00(m，4H)，0.77(t，J＝6.6Hz，3H)； 13C?NMR(75MHz，CDCl 3)δ149.3，147.6，139.7，137.4，132.8，131.9，131.3，128.5，128.4，127.6，126.2，123.8，116.9，89.5，78.8，38.8，29.8，25.1，22.5，13.7；IR(neat，cm -1)：3027，2957，2930，2857，1943，1801，1641，1601，1525，1494，1348，1107，1050，1014，968，898，855，828，750，699；MS(m/z)：389(M +，2.08)，332(M +-C 4H 9，19.22)，91(100)；HRMS?calcd?for?C 25H 27NO 3(M +)：389.1991；found：389.1997.
Embodiment 14
Press embodiment 1 described method, different is that used substrate and reagent are: palladium iodide (7.1mg, 0.020mmol), 1-phenyl-2,3-divinyl-1-alcohol (66.2mg, 0.45mmol), boron trifluoride diethyl etherate (51 μ L, 0.4mmol), 1-p-nitrophenyl-2-normal-butyl-2,3-divinyl-1-alcohol (96.3mg, 0.39mmol), and dimethyl sulfoxide (DMSO) (2mL) product 2-p-nitrophenyl-3-normal-butyl-4-(1 '-methylene radical-3 '-phenyl-2 '-propenyl)-2,5-dihydrofuran 54.9mg, productive rate are 38%.Product is a colourless liquid.
1H?NMR(300?MHz，CDCl 3)δ8.27(d，J＝8.4Hz，2H)，7.54(d，J＝8.4Hz，2H)，7.46-7.20(m，5H)，6.85(d，J＝16.2Hz，1H)，6.50(d，J＝16.2Hz，1H)，5.95-5.85(m，1H)，5.45(s，1H)，5.14(s，1H)，5.05-4.85(m，2H)，2.24-2.08(m，1H)，1.70-1.52(m，1H)，1.48-1.08(m，4H)，0.79(t，J＝7.2Hz，3H)； 13C?NMR(75MHz，CDCl 3)δ149.4，147.7，139.9，138.0，136.6，132.5，131.1，128.8，128.7，128.0，127.6，126.5，123.9，118.7，89.5，78.9，29.8，25.1，22.5，13.7；IR(neat，cm -1)：3080，3058，3026，2957，2930，2858，1801，1599，1522，1494，1449，1347，1272，1107，1050，1014，965，899，855，828，753，694；MS(m/z)：375(M +，5.91)，105(100)；HRMS?calcd?for?C 24H 25NO 3(M +)：375.1834；found：375.1830.
Embodiment 15
Press embodiment 1 described method, different is that used substrate and reagent are: palladium iodide (7.3mg, 0.020mmol), 1-phenyl-3,4-pentadiene-2-alcohol (73.2mg, 0.46mmol), boron trifluoride diethyl etherate (51 μ L, 0.4mmol), 1-Chloro-O-Phenyl-2-normal-butyl-2,3-divinyl-1-alcohol (93.6mg, 0.40mmol), and dimethyl sulfoxide (DMSO) (2mL) product 2-Chloro-O-Phenyl-3-normal-butyl-4-(1 '-methylene radical-4 '-phenyl-2 '-butenyl)-2,5-dihydrofuran 97.3mg, productive rate are 65%.Product is a colourless liquid.
1H?NMR(300MHz，CDCl 3)δ7.40-7.08(m，9H)，6.32-6.22(m，1H)，6.18(d，J＝15.6Hz，1H)，5.89(dt，J 1＝15.6Hz，J 2＝6.9Hz，1H)，5.22(s，1H)，4.98(s，1H)，4.87(ddd，J 1＝12.0Hz，J 2＝5.4Hz，J 3＝3.1Hz，1H)，4.83(dd，J 1＝12.0Hz，J 2＝3.0Hz，1H)，3.45(d，J＝6.9Hz，2H)，2.22-2.06(m，1H)，1.70-1.53(m，1H)，1.40-1.00(m?4H)，0.75(t，J＝6.9Hz，3H)； 13C?NMR(75MHz，CDCl 3)δ140.2，139.8，139.0，137.9，133.2，132.6，131.8，131.5，129.5，129.0，128.4，127.1，126.1，116.6，86.6，78.4，38.8，30.1，25.3，22.6，13.7；IR(neat，cm -1)：3084，3062，3026，2956，2930，2858，1801，1641，1593，1573，1494，1471，1453，1442，1379，1277，1260，1230，1195，1035，968，895；MS(m/z)：380(M +( 37Cl)，27.76)，378(M +( 35Cl)，68.06)，323(M +( 37Cl)-C 4H 9，2.36)，321(M +( 35Cl)-C 4H 9，7.09)，287(100)；HRMS?calcd?for?C 25H 27OCl(M +)：378.1750( 35Cl)；found：378.1749( 35Cl).
Embodiment 16
Press embodiment 1 described method, different is that used substrate and reagent are: and palladium iodide (7.1mg, 0.020mmol), 1, and 2-decadiene-4-alcohol (69.7mg, 0.45mmol), boron trifluoride diethyl etherate (51 μ L, 0.4mmol), 4-ester group-4,5-hexadiene-3-alcohol (61.0mg, 0.39mmol), and dimethyl sulfoxide (DMSO) (2mL) product 2-ethyl-3-ester group-4-(1 '-methylene radical-2 '-nonene base)-2,5-dihydrofuran 59.0mg, productive rate are 52%.Product is a colourless liquid.
1H?NMR(400MHz，CDCl 3)δ6.04(d，J＝15.6Hz，1H)，5.54(dt，J 1＝15.6Hz，J 2＝8.4Hz，1H)，5.16-5.06(m，1H)，5.10(s，1H)，4.86(s，1H)，4.73(dd，J 1＝15.2Hz，J 2＝6.0Hz，1H)，4.64(dd，J 1＝15.2Hz，J 2＝3.6Hz，1H)，3.62(s，3H)，2.03(q，J＝7.2Hz，2H)，1.90-1.77(m，1H)，1.76-1.62(m，1H)，138-1.14(m，8H)，0.91(t，J＝7.6Hz，3H)，0.83(t，J＝7.6Hz，3H)； 13C?NMR(100MHz，CDCl 3)δ163.3，149.6，139.8.133.3，129.0，128.9，114.4，87.9，78.8，51.1，32.4，31.5，28.9，28.6，27.4，22.4，13.9，8.7，IR(neat，cm -1)：2958，2927，2855，1716，1665，1592，1458，1437，1280，1249，1154，1192，1154，1065，1035，965，889；MS(m/z)：292(M +，48.94)，263(100)；HRMS?calcd?forC 18H 28O 3(M +)：292.2033；found：292.2038.
Embodiment 17
Press embodiment 1 described method, different is that used substrate and reagent are: and palladium iodide (7.2mg, 0.020mmol), 1-phenyl-3, and 4-pentadiene-2-alcohol (77.1mg, 0.48mmol), boron trifluoride diethyl etherate (51 μ L, 0.4mmol), 4-ester group-4,5-hexadiene-3-alcohol (61.0mg, 0.39mmol), and dimethyl sulfoxide (DMSO) (2mL) product 2-ethyl-3-ester group-4-(1 '-methylene radical-4 '-phenyl-2 '-butenyl)-2,5-dihydrofuran 62.6mg, productive rate are 52%.Product is a colourless liquid.
1H?NMR(300MHz，CDCl 3)δ7.25-7.00(m，5H)，6.09(d，J＝15.9Hz，1H)，5.67(dt，J 1＝15.9Hz，J 2＝6.9Hz，1H)，5.14(s，1H)，5.12-5.02(m，1H)，4.90(s，1H)，4.71(dd，J 1＝15.0Hz，J 2＝2.7Hz，1H)，4.72(dd，J 1＝15.0Hz，J 2＝3.6Hz，1H)，3.54(s，3H)，3.36(d，J＝6.9Hz，2H)，1.88-1.72(m，1H)，1.71-1.55(m，1H)，0.86(t，J＝7.2Hz，3H)； 13C?NMR(75MHz，CDCl 3)δ163.3，149.4，139.7，139.5，131.3，130.5，129.1，128.5，128.4，126.1，115.7，88.0，78.8，51.3，38.8，27.5，8.8；IR(neat，cm -1)：3086，3062?3027，2964，2933，2848，1713，1666，1602，1495，1454，1436，1363，1251，1193，1152，1065，1032，967，896，749，700；MS(m/z)：298(M +，4.43)，91(100)；HRMS?calcd?forC 19H 22O 3(M +)：298.1569；found：298.1561.
Embodiment 18
Press embodiment 1 described method, different is that used substrate and reagent are: and palladium iodide (7.4mg, 0.020mmol), 1-phenyl-3, and 4-pentadiene-2-alcohol (78.9mg, 0.49mmol), boron trifluoride diethyl etherate (51 μ L, 0.4mmol), 3-ester group-1,2-nonadiene-4-alcohol (81.5mg, 0.41mmol), and dimethyl sulfoxide (DMSO) (2mL) product 2-amyl group-3-ester group-4-(1 '-methylene radical-4 '-phenyl-2 '-butenyl)-2,5-dihydrofuran 74.4mg, productive rate are 53%.Product is a colourless liquid.
1H?NMR(300MHz，CDCl 3)δ7.23-7.00(m，5H)，6.08(d，J＝15.6Hz，1H)，5.67(dt，J 1＝15.6Hz，J 2＝6.9Hz，1H)，5.14(s，1H)，5.14-5.02(m，1H)，4.89(s，1H)，4.70(dd，J 1＝15.0Hz，J 2＝2.7Hz，1H)，4.60(dd，J 1＝15.0Hz，J 2＝3.0Hz，1H)，3.53(s，3H)，3.35(d，J＝6.9Hz，2H)，1.81-1.65(m，1H)，1.64-1.50(m，1H)，1.40-1.27(m，2H)，1.26-1.10(m，4H)，0.86-0.70(m，3H)； 13C?NMR(75MHz，CDCl 3)δ163.3，149.0，139.6，139.5，131.3，130.4，129.6，128.44，128.3?6，126.1，115.6，87.2，78.6，51.2，38.8，34.6，31.7，24.6，22.5，14.0；IR(neat，cm -1)：3086，3062，3027，2955，2928，2858，1716，1666，1602，1495，1454，1436，1361，1252，1194，1152，1106，1071，102a?966，894，789，749，699；MS(m/z)：340(M +，11.64)，269(M +-C 5H 11，65?20)，91(100)；HRMS?calcd?for?C 22H 28O 3(M +)：340.203；found：340.2045.
Embodiment 19
Press embodiment 1 described method, different is that used substrate and reagent are: and palladium iodide (7.2mg, 0.020mmol), 1-phenyl-3, and 4-pentadiene-2-alcohol (70.8mg, 0.44mmol), boron trifluoride diethyl etherate (51 μ L, 0.4mmol), 3-phenyl-1,2-octadiene-4-alcohol (80.6mg, 0.40mmol), and dimethyl sulfoxide (DMSO) (2mL) product 2-normal-butyl-3-phenyl-4-(1 '-methylene radical-4 '-phenyl-2 '-butenyl)-2,5-dihydrofuran 70.9mg, productive rate are 48%.Product is a colourless liquid.
1H?NMR(300?MHz，CDCl 3)4.630-7.00(m，8H)，6.87(d，J＝6.6Hz，2H)，5.95(d，J＝15.9Hz，1H)，5.73(dt，J 1＝15.9Hz，J 2＝6.9Hz，1H)，5.35-5.25(m，1H)，5.11(s，1H)，4.89(s，1H)，4.85(dd，J 1＝12.9Hz，J 2＝5.7Hz，1H)，4.64(dd，J 1＝12.9Hz，J 2＝3.3Hz，1H)，3.2(d，J＝6.9Hz，2H)，1.66-1.50(m，1H)，1.50-1.36(m，1H)，1.35-1.23(m，2H)，1.22-1.06(m，2H)，0.73(t，J＝6.9Hz，3H)； 13C?NMR(75MHz，CDCl 3)δ140.6，139.8，136.8，133.9，133.1，131.6，131.0，128.4，128.3，128.1，127.7，127.3，125.9，116.6，88.7，79.0，38.6，34.2，27.0，22.7，14.0；IR(neat，cm -1)：3084，3060，3027，2956，2930，2858，1943，1865，1801，1685，1602，1495，1453，1378，1350，1296，1051，968，893；MS(m/z)：344(M +，7.60)，91(100)；HRMS?calcd?for?C 25H 28O(M +)：344.2140；found：344.2133.

Claims (4)

1. synthetic 4-(1 ', 3 '-conjugated diolefine-2 '-yl)-2, the method of 5-dihydrofuran is characterized in that by 2 of a part 2 of replacement being arranged, and 2 of 3-connection enol and another molecules do not have 2 of replacement, 3-connection enol is under the effect of the catalysis of palladium iodide and an equivalent boron trifluoride diethyl etherate, intermolecular cross-coupling reaction takes place, and synthetic 4-(1 ', 3 '-conjugated diolefine-2 '-yl)-2, the 5-dihydrofuran, reaction formula is as follows:
R 1=alkyl, phenyl, allyl group, ester group; R 2=alkyl, aryl; R 3=alkyl, phenyl the steps include:
(1) at room temperature, get 2 of raw materials 2 of replacement is arranged, 3-connection enol, palladium iodide, organic solvent dimethyl sulfoxide (DMSO), boron trifluoride diethyl etherate, 2 do not replace 2,3-joins enol, by 22 of replacement is arranged, 3-connection enol and palladium iodide, dimethyl sulfoxide (DMSO), 2 do not replace 2, the mol ratio that 3-joins between enol and the equivalent boron trifluoride diethyl etherate is respectively: 1: 0.05; 0.98～1.09mmol/5mL; 1: 1.1～1.3; 1: 0.98～1.09 ratio is reinforced, order is: past 2 do not have 2 of replacement, add the organic solvent dimethyl sulfoxide (DMSO) of half in 3-connection enol and the palladium iodide mixture successively, an equivalent boron trifluoride diethyl etherate, 2 have 2 of replacement, 3-connection enol and second half organic solvent dimethyl sulfoxide (DMSO);
(2), be as cold as room temperature and add shrend and go out extracted with diethyl ether 80 ℃ of heated and stirred reaction 0.5～1.5 hour;
(3) concentrate, rapid column chromatography, acquisition 4-(1 ', 3 '-conjugated diolefine-2 '-yl)-2, the 5-dihydrofuran.
2. synthetic 4-according to claim 1 (1 ', 3 '-conjugated diolefine-2 '-yl)-2, the method for 5-dihydrofuran, it is characterized in that 2 do not replace 2,3-connection enol and 2 have 2 of replacement, the mol ratio of 3-connection enol is: 1.1: 1.
3. (1 ', 3 '-conjugated diolefine-2 '-yl)-2, the method for 5-dihydrofuran is characterized in that 2 have 2 of replacement to synthetic 4-according to claim 1, and the mol ratio of 3-connection enol and dimethyl sulfoxide (DMSO) is: 1mmol/5mL.
4. (1 ', 3 '-conjugated diolefine-2 '-yl)-2, the method for 5-dihydrofuran is characterized in that 2 have 2 of replacement to synthetic 4-according to claim 7, and the mol ratio of 3-connection enol and boron trifluoride diethyl etherate is: 1: 1.
CN2008100605583A 2008-03-27 2008-03-27 Method for synthesizing 4-(1', 3'-conjugated diene-2'-group)-2,5-dihydrofuran Expired - Fee Related CN101250170B (en)

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CN103588739A (en) * 2011-03-25 2014-02-19 上海长恒生物医药科技有限公司 Nitrofurans compounds, preparation method and application of nitrofurans compounds
CN108794437A (en) * 2018-09-10 2018-11-13 河南师范大学 A kind of synthetic method of 2- (3- furyls) acetamides
CN108794437B (en) * 2018-09-10 2022-11-15 河南师范大学 Synthetic method of 2- (3-furyl) acetamide compound

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