PL237141B1 - Method of preparing 3-(furan-2"-yl)-1-(2'-hydroxyphenyl)propan-1-one - Google Patents
Method of preparing 3-(furan-2"-yl)-1-(2'-hydroxyphenyl)propan-1-one Download PDFInfo
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- PL237141B1 PL237141B1 PL426767A PL42676718A PL237141B1 PL 237141 B1 PL237141 B1 PL 237141B1 PL 426767 A PL426767 A PL 426767A PL 42676718 A PL42676718 A PL 42676718A PL 237141 B1 PL237141 B1 PL 237141B1
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- hydroxyphenyl
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- 238000000034 method Methods 0.000 title claims abstract description 12
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 title 1
- 241000235015 Yarrowia lipolytica Species 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- 230000008569 process Effects 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 4
- RLRWAEXMKRTNRV-UHFFFAOYSA-N 3-(furan-2-yl)-1-(2-hydroxyphenyl)propan-1-one Chemical compound OC1=CC=CC=C1C(=O)CCC1=CC=CO1 RLRWAEXMKRTNRV-UHFFFAOYSA-N 0.000 claims description 3
- 238000004587 chromatography analysis Methods 0.000 claims description 3
- 230000009466 transformation Effects 0.000 claims description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 4
- 230000009467 reduction Effects 0.000 abstract description 2
- 102000004190 Enzymes Human genes 0.000 abstract 1
- 108090000790 Enzymes Proteins 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 244000005700 microbiome Species 0.000 abstract 1
- JECYUBVRTQDVAT-UHFFFAOYSA-N 2-acetylphenol Chemical compound CC(=O)C1=CC=CC=C1O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229940002520 2'-hydroxyacetophenone Drugs 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGGZBXOADPVUPN-UHFFFAOYSA-N dihydrochalcone Chemical group C=1C=CC=CC=1C(=O)CCC1=CC=CC=C1 QGGZBXOADPVUPN-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- VGEREEWJJVICBM-UHFFFAOYSA-N phloretin Chemical compound C1=CC(O)=CC=C1CCC(=O)C1=C(O)C=C(O)C=C1O VGEREEWJJVICBM-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- ZWTDXYUDJYDHJR-UHFFFAOYSA-N (E)-1-(2,4-dihydroxyphenyl)-3-(2,4-dihydroxyphenyl)-2-propen-1-one Natural products OC1=CC(O)=CC=C1C=CC(=O)C1=CC=C(O)C=C1O ZWTDXYUDJYDHJR-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- JCPGMXJLFWGRMZ-UHFFFAOYSA-N 2-hydroxy-beta-phenylpropiophenone Natural products OC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 JCPGMXJLFWGRMZ-UHFFFAOYSA-N 0.000 description 1
- RTGXXLFEOHIIBM-UHFFFAOYSA-N 3-(furan-2-yl)-1-(2-hydroxyphenyl)prop-2-en-1-one Chemical compound OC1=CC=CC=C1C(=O)C=CC1=CC=CO1 RTGXXLFEOHIIBM-UHFFFAOYSA-N 0.000 description 1
- BJGDMOPWBQPTDI-UHFFFAOYSA-N 3-cyclohexa-2,4-dien-1-yl-1-(2-hydroxyphenyl)prop-2-en-1-one Chemical compound OC1=CC=CC=C1C(=O)C=CC1C=CC=CC1 BJGDMOPWBQPTDI-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- YQHMWTPYORBCMF-UHFFFAOYSA-N Naringenin chalcone Natural products C1=CC(O)=CC=C1C=CC(=O)C1=C(O)C=C(O)C=C1O YQHMWTPYORBCMF-UHFFFAOYSA-N 0.000 description 1
- 102000003425 Tyrosinase Human genes 0.000 description 1
- 108060008724 Tyrosinase Proteins 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000010352 biotechnological method Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- PXLWOFBAEVGBOA-UHFFFAOYSA-N dihydrochalcone Natural products OC1C(O)C(O)C(CO)OC1C1=C(O)C=CC(C(=O)CC(O)C=2C=CC(O)=CC=2)=C1O PXLWOFBAEVGBOA-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000004217 heart function Effects 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- JWHAUXFOSRPERK-UHFFFAOYSA-N propafenone Chemical compound CCCNCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 JWHAUXFOSRPERK-UHFFFAOYSA-N 0.000 description 1
- 229960000203 propafenone Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000019605 sweet taste sensations Nutrition 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/04—Oxygen as only ring hetero atoms containing a five-membered hetero ring, e.g. griseofulvin, vitamin C
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- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
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Abstract
Zgłoszenie dotyczy sposobu wytwarzania 3-(furan-2"-ylo)-1-(2'-hydroksyfenylo)-propan-1-onu o wzorze 2. W wyniku działania układu enzymatycznego zawartego w komórkach szczepu Yarrowia lipolytica KCh 71, następuje regioselektywna redukcja podwójnego wiązania w substracie. Uzyskany w ten sposób produkt wydziela się z wodnej kultury mikroorganizmu, znanym sposobem, przez ekstrakcję rozpuszczalnikiem organicznym niemieszającym się z wodą (chloroform).The application concerns a method of producing 3-(furan-2"-yl)-1-(2'-hydroxyphenyl)-propan-1-one of the formula 2. As a result of the action of the enzyme system contained in the cells of the Yarrowia lipolytica KCh 71 strain, regioselective reduction of The product thus obtained is separated from the aqueous culture of the microorganism in a known manner by extraction with a water-immiscible organic solvent (chloroform).
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest sposób wytwarzania 3-(furan-2''-ylo)-1-(2'-hydroksyfenylo)-propan-1-onu.The present invention relates to a process for the preparation of 3- (furan-2 '' - yl) -1- (2'-hydroxyphenyl) propan-1-one.
Metoda, według wynalazku może znaleźć zastosowanie w przemyśle spożywczym jako środek słodzący i farmaceutycznym jako prekursor leków regulujących pracę serca.The method according to the invention may find application in the food industry as a sweetener and in pharmaceuticals as a precursor of drugs regulating the heart function.
Dihydrochalkony są syntezowane przez rośliny i charakteryzują się słodkim smakiem. Również syntetyczne związki posiadające ugrupowanie dihydrochalkonu wykazują wysokie wrażenie słodkości (Winnig M, Bufe B, Kratochwil NA, Slack JP, Meyerhof W. 2007 BMC Struct. Biol. 7, 66; Krammer G. Ley J, Riess T, Haug M, Paetz S, Kindel G, Schmidtmann R. Patent No.: US 20100233102; Sep, 16, 2010. Encyclopedia of Food Science, Food Technology and Nutrition. Academic Press, London 1993, Krutosikowa A., Uher M.: Naturalne i syntetyczne substancje o słodkim smaku. PWN, Warszawa 1990; 2'-Hydroksydihydrochalkon jest wykorzystywany jako blok budulcowy w syntezie propafenonu - substancji czynnej leków przeciwarytmicznych (Noe GR, Knollmuller M, Oberhauser B, Steinbauer G, Wagner E. 1986 Chemische Berichte, 119, 729-743; Ecker G, Chiba P, Hitzler M, Schmid D, Visser K, Cordes HP, Csollei J, Seydel JK, Schaper K-J. 1996 J. Med. Chem. 39, 4767-4774; Ecker G, Noe CR, Fleischhacker W. 1997 Monatsh. Chem. 128, 53-59). Znana jest również ich aktywność względem patogennych mikroorganizmów, w tym gram-dodatnich i gram-ujemnych bakterii oraz grzybów (Awouafack MD, Kusari S, Lamshoft M, Ngamga D, Tane P, Spiteller M. 2010 Planta Med. 76, 640-643). Dihydrochalkon (floretyna) jest aktywnym inhibitorem tyrozynazy grzybowej (Zhang L-Q, Yang X-W, Zhang Y-B, Zhai Y-Y, Xu W, Zhao B, Liu D-L, Yu H-J. 2012 Food Chem. 132, 936-942).Dihydrochalcones are synthesized by plants and have a sweet taste. Also, synthetic compounds having a dihydrochalcone group show a high sweetness impression (Winnig M, Bufe B, Kratochwil NA, Slack JP, Meyerhof W. 2007 BMC Struct. Biol. 7, 66; Krammer G. Ley J, Riess T, Haug M, Paetz S , Kindel G, Schmidtmann R. Patent No .: US 20100233102; Sep, 16, 2010. Encyclopedia of Food Science, Food Technology and Nutrition. Academic Press, London 1993, Krutosikowa A., Uher M .: Natural and synthetic sweet substances taste, PWN, Warsaw 1990; 2'-Hydroxydihydrochalcone is used as a building block in the synthesis of propafenone - the active substance of antiarrhythmic drugs (Noe GR, Knollmuller M, Oberhauser B, Steinbauer G, Wagner E. 1986 Chemische Berichte, 119, 729-743; Ecker G, Chiba P, Hitzler M, Schmid D, Visser K, Cordes HP, Csollei J, Seydel JK, Schaper KJ. 1996 J. Med. Chem. 39, 4767-4774; Ecker G, Noe CR, Fleischhacker W. 1997 Monatsh. Chem. 128, 53-59). Their activity against pathogenic microorganisms is also known, including g ram-positive and gram-negative bacteria and fungi (Awouafack MD, Kusari S, Lamshoft M, Ngamga D, Tane P, Spiteller M. 2010 Planta Med. 76, 640-643). Dihydrochalcone (phloretin) is an active inhibitor of fungal tyrosinase (Zhang L-Q, Yang X-W, Zhang Y-B, Zhai Y-Y, Xu W, Zhao B, Liu D-L, Yu H-J. 2012 Food Chem. 132, 936-942).
Szczep Yarrowia lipolytica KCh 71 był wcześniej ujawniony w literaturze (Janeczko T, Gładkowski W, Kostrzewa-Susłow E. 2013 J. Mol. Cat. B-Enzym. 98, 55-61; Janeczko T, Dymarska M, Siepka M, Gniłka R, Leśniak A, Popłoński J, Kostrzewa-Susłow E. 2014 J. Mol. Cat. B-Enzym. 109, 47-52; Janeczko T, Kostrzewa-Susłow E. 2014 Tetrahedron: Asymmetry, 25, 1264-1269).The Yarrowia lipolytica KCh 71 strain was previously disclosed in the literature (Janeczko T, Gładkowski W, Kostrzewa-Susłow E. 2013 J. Mol. Cat. B-Enzym. 98, 55-61; Janeczko T, Dymarska M, Siepka M, Gśmieka R) , Leśniak A, Popłoński J, Kostrzewa-Susłow E. 2014 J. Mol. Cat. B-Enzym. 109, 47-52; Janeczko T, Kostrzewa-Susłow E. 2014 Tetrahedron: Asymmetry, 25, 1264-1269).
Znany jest sposób uzyskania 3-(furan-2''-ylo)-1-(2'-hydroksyfenylo)-propan-1-onu z konwersją 75% w wyniku syntezy chemicznej 2'-hydroksyacetofenonu i alkoholu furfurylowego z NaOH w obecności katalizatora irydowego (Hunter J., Rice S., Lowe R., Pask C.M., Warriner S., Sridharan V. Iridium catalyzed alkylation of 2'-hydroxyacetophenone with alcohols under thermal or microwave conditions. Tetrahedron: Letters 58 (2017) 4400-4402). W literaturze nie ma doniesień dotyczących zastosowania metod biotechnologicznych do uzyskania 3-(furan-2''-ylo)-1-(2'-hydroksyfenylo)-propan-1-onu.There is a known method of obtaining 3- (furan-2 '' - yl) -1- (2'-hydroxyphenyl) -propan-1-one with 75% conversion as a result of chemical synthesis of 2'-hydroxyacetophenone and furfuryl alcohol from NaOH in the presence of a catalyst iridowego (Hunter J., Rice S., Lowe R., Pask CM, Warriner S., Sridharan V. Iridium catalyzed alkylation of 2'-hydroxyacetophenone with alcohols under thermal or microwave conditions. Tetrahedron: Letters 58 (2017) 4400-4402 ). There are no reports in the literature on the use of biotechnological methods to obtain 3- (furan-2 '' - yl) -1- (2'-hydroxyphenyl) -propan-1-one.
Istota wynalazku polega na tym, że do podłoża odpowiedniego dla drożdży wprowadza się szczep Yarrowia lipolytica KCh 71. Po upływie co najmniej 48 godzin do hodowli wprowadza się substrat, którym jest 3-(furan-2-ylo)-1-(2'-hydroksyfenylo)-prop-2-en-1-on o wzorze 1, rozpuszczony w rozpuszczalniku organicznym mieszającym się z wodą. Transformację prowadzi się w temperaturze od 20 do 30 stopni Celsjusza, przy ciągłym wstrząsaniu, co najmniej 1 godzinę. Kolejno produkt ekstrahuje się rozpuszczalnikiem organicznym niemieszającym się z wodą i oczyszcza chromatograficznie.The essence of the invention consists in introducing the Yarrowia lipolytica KCh 71 strain into a medium suitable for yeast. After at least 48 hours, a substrate, which is 3- (furan-2-yl) -1- (2'-), is introduced into the culture. hydroxyphenyl) -prop-2-en-1-one of formula 1, dissolved in a water-miscible organic solvent. The transformation is carried out at a temperature of 20 to 30 degrees Celsius with continuous shaking for at least 1 hour. Subsequently, the product is extracted with a water-immiscible organic solvent and purified by chromatography.
Korzystnie jest, gdy stosunek masy dodawanego substratu do objętości hodowli wynosi 0,2 g : 1 L.Preferably, the ratio of the mass of the added substrate to the culture volume is 0.2 g: 1 L.
Korzystnie także jest, gdy proces prowadzi się w temperaturze 25 stopni Celsjusza.It is also preferred that the process is carried out at a temperature of 25 degrees Celsius.
W wyniku regioselektywnej redukcji podwójnego wiązania otrzymuje się 3-(furah-2-ylo)-1-(2'-hydroksyfenylo)-propan-1-on, a reakcję prowadzi się w wodnej kulturze szczepu Yarrowia lipolytica KCh 71.The regioselective reduction of the double bond yields 3- (furah-2-yl) -1- (2'-hydroxyphenyl) -propan-1-one, and the reaction is carried out in an aqueous culture of the strain Yarrowia lipolytica KCh 71.
Zasadniczą zaletą wynalazku jest otrzymanie 3-(furan-2-ylo)-1-(2'-hydroksyfenylo)-propan-1-onu, z wydajnością izolowaną na poziomie 30% (konwersją według GC = 98%), w temperaturze pokojowej i przy pH naturalnym dla szczepu.The main advantage of the invention is the preparation of 3- (furan-2-yl) -1- (2'-hydroxyphenyl) -propan-1-one, with an isolated yield of 30% (conversion according to GC = 98%), at room temperature and at the natural pH of the strain.
Wynalazek jest bliżej objaśniony na przykładzie wykonania.The invention is explained in more detail using an exemplary embodiment.
P r z y k ł a d. Do kolby Erlenmajera o pojemności 2000 cm3, w której znajduje się 500 cm3 sterylnej pożywki zawierającej 5 g aminobaku i 15 g glukozy, wprowadza się szczep Yarrowia lipolytica KCh 71. Po 72 godzinach jego wzrostu dodaje się 100 mg 3-(furan-2-ylo)-1-(2'-hydroksyfenylo)-prop-2-en-1-on o wzorze 1, rozpuszczonego w 1 cm3 tetrahydrofuranu (THF). Transformację prowadzi się w 25 stopniach Celsjusza przy ciągłym wstrząsaniu przez 24 godziny. Następnie mieszaninę poreakcyjną ekstrahuje się trzykrotnie chloroformem, osusza bezwodnym siarczanem magnezu i odparowuje rozpuszczalnik. Otrzymany ekstrakt oczyszcza się chromatograficznie, używając jako eluentu mieszaniny heksan i aceton 9:1.Example: The Yarrowia lipolytica KCh 71 strain is introduced into an Erlenmajer flask with a capacity of 2000 cm 3 , containing 500 cm 3 of sterile medium containing 5 g of aminobac and 15 g of glucose. After 72 hours of its growth, 100 mg is added 3- (furan-2-yl) -1- (2'-hydroxyphenyl) prop-2-en-1-one of formula 1, dissolved in 1 cm 3 of tetrahydrofuran (THF). The transformation is carried out at 25 degrees Celsius with continuous shaking for 24 hours. The reaction mixture was then extracted three times with chloroform, dried with anhydrous magnesium sulfate, and the solvent was evaporated. The extract obtained is purified by chromatography using a 9: 1 mixture of hexane and acetone as the eluent.
Na tej drodze otrzymuje się 3-(furan-2-ylo)-1-(2'-hydroksyfenylo)-propan-1-on (konwersja według GC na poziomie 90%).In this way, 3- (furan-2-yl) -1- (2'-hydroxyphenyl) propan-1-one is obtained (GC conversion 90%).
PL 237 141 B1PL 237 141 B1
Uzyskany produkt charakteryzuje się następującymi danymi spektralnymi:The obtained product is characterized by the following spectral data:
1H NMR (600 MHz) (CDCI3) δ (ppm): 3.07-3.12 (m, 2H, H-3), 3.34-3,41 (m, 2H, H-2), 6.06 (dq, 1H, J = 3.2, 0.8 Hz, H-5''), 6.29 (dd, 1H, J = 3.1, 1.9 Hz, H-4), 6.90 (ddd, 1H, J = 8.2, 7.1, 1.2 Hz, H-5'), 7.02 (dd, 1H, J = 8.4, 0.9 Hz, H-3'), 7.32 (dd, 1H, J = 1.8, 0.8 Hz, H-3''), 7.49 (ddd, 1H, J = 8.5, 7.2, 1.6 Hz, H-4'), 7.92 (dd, 1H, J = 8.0, 1.6 Hz, H-6'), 12.23 (s, 1H, - O H). 1 H NMR (600 MHz) (CDCl 3) δ (ppm): 3.07-3.12 (m, 2H, H-3), 3.34-3.41 (m, 2H, H-2), 6.06 (dq, 1H, J = 3.2, 0.8 Hz, H-5 "), 6.29 (dd, 1H, J = 3.1, 1.9 Hz, H-4), 6.90 (ddd, 1H, J = 8.2, 7.1, 1.2 Hz, H-5 ' ), 7.02 (dd, 1H, J = 8.4, 0.9 Hz, H-3 '), 7.32 (dd, 1H, J = 1.8, 0.8 Hz, H-3''), 7.49 (ddd, 1H, J = 8.5 , 7.2, 1.6 Hz, H-4 '), 7.92 (dd, 1H, J = 8.0,1.6 Hz, H-6'), 12.23 (s, 1H, - OH).
13C NMR (151 MHz, CDCI3) δ = 22.50 (C-3), 36.73 (C-2), 105.69 (C-5''), 110.44 (C-4), 118.72 (C-3'), 119.12 (C-5'), 119.40 (C-1'). 129.94 (C-6'), 136.56: (C-4'), 141.41 (C-3), 154.33 (C-1), 162.56 (C-2'), 204.90 (C-1). 13 C NMR (151 MHz, CDCl 3) δ = 22.50 (C-3), 36.73 (C-2), 105.69 (C-5 "), 110.44 (C-4), 118.72 (C-3 '), 119.12 (C-5 '), 119.40 (C-1'). 129.94 (C-6 '), 136.56: (C-4'), 141.41 (C-3), 154.33 (C-1), 162.56 (C-2 '), 204.90 (C-1).
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| PL426767A1 PL426767A1 (en) | 2020-02-24 |
| PL237141B1 true PL237141B1 (en) | 2021-03-22 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL426767A PL237141B1 (en) | 2018-08-23 | 2018-08-23 | Method of preparing 3-(furan-2"-yl)-1-(2'-hydroxyphenyl)propan-1-one |
Country Status (1)
| Country | Link |
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| PL (1) | PL237141B1 (en) |
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| Publication number | Publication date |
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| PL426767A1 (en) | 2020-02-24 |
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