PL236887B1 - Derivative of thiophene and method for obtaining it - Google Patents
Derivative of thiophene and method for obtaining it Download PDFInfo
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- PL236887B1 PL236887B1 PL422238A PL42223817A PL236887B1 PL 236887 B1 PL236887 B1 PL 236887B1 PL 422238 A PL422238 A PL 422238A PL 42223817 A PL42223817 A PL 42223817A PL 236887 B1 PL236887 B1 PL 236887B1
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- methylthiophen
- butan
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- 150000003577 thiophenes Chemical class 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims abstract description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000005886 esterification reaction Methods 0.000 claims abstract description 8
- JVFWKWMSTLLUGZ-UHFFFAOYSA-N 4-(3-methylthiophen-2-yl)butan-2-ol Chemical compound CC(O)CCC=1SC=CC=1C JVFWKWMSTLLUGZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- ZZWFNQZJQBZOMJ-UHFFFAOYSA-N C(C)(=O)OC(CCC=1SC=CC=1C)C Chemical compound C(C)(=O)OC(CCC=1SC=CC=1C)C ZZWFNQZJQBZOMJ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 230000032050 esterification Effects 0.000 claims abstract description 7
- WJOQKGDEHMJAJV-UHFFFAOYSA-N 4-(3-methylthiophen-2-yl)butan-2-one Chemical compound CC(=O)CCC=1SC=CC=1C WJOQKGDEHMJAJV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000012429 reaction media Substances 0.000 claims abstract description 5
- 238000006722 reduction reaction Methods 0.000 claims abstract description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 claims abstract description 4
- 239000012279 sodium borohydride Substances 0.000 claims abstract description 4
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000004587 chromatography analysis Methods 0.000 claims abstract description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- YOSDTJYMDAEEAZ-UHFFFAOYSA-N 2-acetyl-5-methylthiophene Chemical compound CC(=O)C1=CC=C(C)S1 YOSDTJYMDAEEAZ-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical compound CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- QENGPZGAWFQWCZ-UHFFFAOYSA-N Methylthiophene Natural products CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000006254 arylation reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Przedmiotem zgłoszenia jest nowa pochodna tiofenu, octan 4-(3-metylotiofen-2-ylo)-butan-2-olu o wzorze 1. Zgłoszenie obejmuje też sposób otrzymywania pochodnej tiofenu, octanu 4-(3-metylotiofen-2-ylo)-butan-2-olu o wzorze 1, który polega na tym, że 4-(3-metylotiofen-2-ylo)-butan-2-on poddaje się reakcji redukcji borowodorkiem sodu w środowisku metanolu, a otrzymany w tej reakcji 4-(3-metylotiofen-2-ylo)-butan-2-ol, po wyodrębnieniu ze środowiska reakcji, poddaje się reakcji estryfikacji bezwodnikiem octowym w obecności pirydyny w środowisku dichlorometanu, zaś produkt estryfikacji, po wyodrębnieniu ze środowiska reakcji, oczyszcza się chromatograficznie.The subject of the application is a new thiophene derivative, 4-(3-methylthiophen-2-yl)-butan-2-ol acetate of formula 1. The application also includes a method for obtaining a thiophene derivative, 4-(3-methylthiophen-2-yl)-acetate butan-2-ol of the formula 1, which consists in the fact that 4-(3-methylthiophen-2-yl)-butan-2-one is subjected to a reduction reaction with sodium borohydride in methanol, and the 4-( 3-Methylthiophen-2-yl)-butan-2-ol, after being isolated from the reaction medium, is subjected to esterification with acetic anhydride in the presence of pyridine in dichloromethane, and the esterification product, after being isolated from the reaction medium, is purified by chromatography.
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest nowy związek, pochodna tiofenu oraz sposób jej otrzymywania.The subject of the invention is a new compound, a thiophene derivative and the method of its preparation.
Tiofen stanowi fragment strukturalny licznych związków aktywnych sensorycznie, zarówno pochodzenia naturalnego jak i syntetycznego (Safety evolution of substituted thiophene used as flavoring ingredients., Food and Chemical Toxicology, 99, s 40-59, 2016).Thiophene is a structural fragment of numerous sensory active compounds, both of natural and synthetic origin (Safety evolution of substituted thiophene used as flavoring ingredients., Food and Chemical Toxicology, 99, pp. 40-59, 2016).
Znana jest pochodna tiofenu, którą stanowi 2-acetylo-5-metylotiofen o wzorze AThe thiophene derivative 2-acetyl-5-methylthiophene of formula A is known
O wzór AAbout pattern A
Pochodną tę otrzymuje się w procesie dwuetapowym - przez metylowanie tiofenu jodkiem metylu i następnie arylowanie powstałego w reakcji metylowania 2-metylotiofenu chlorkiem acetylu w obecności bezwodnego chlorku glinowego.This derivative is obtained in a two-stage process - by methylation of thiophene with methyl iodide and then arylation of the 2-methylthiophene resulting from the methylation reaction with acetyl chloride in the presence of anhydrous aluminum chloride.
Przedmiotem wynalazku jest nowa pochodna tiofenu, którą stanowi racemiczny octan 4-(3-metylotiofen-2-ylo)-butan-2-olu o wzorze 1The subject of the invention is a new thiophene derivative, which is racemic 4- (3-methylthiophen-2-yl) -butan-2-ol acetate of the formula 1
ΎΎ
O wzór 1About formula 1
Nowa pochodna tiofenu o wzorze 1, stanowiąca mieszaninę dwóch enancjomerów, jest cieczą o barwie jasnosłomkowej, charakteryzującą się bardzo przyjemnym, owocowym zapachem przypominającym aromat pigłowca z nutą limonki. Dane spektralne nowego związku, octanu 4-(3-metylotiofen2-ylo)-butan-2-olu są następujące:The new thiophene derivative of formula 1, which is a mixture of two enantiomers, is a light straw-colored liquid characterized by a very pleasant, fruity aroma reminiscent of the aroma of pigwood with a hint of lime. The spectral data of the new compound, 4- (3-methylthiophen-2-yl) -butan-2-ol acetate are as follows:
H1-NMR (CDCh), 7.00 ppm (d 1 H-1), 6.77 ppm (d 1 H-2), 4.93 ppm (m 1 H-8), 2.76 ppm (m 2 H-6), 2.15 ppm (s 3 H-5), 2.05 ppm (s 3 H-11), 1.94 -1.78 ppm (m 2 H-7), 1.25 ppm (d 3 H-9);H 1 -NMR (CDCl 3), 7.00 ppm (d 1 H-1), 6.77 ppm (d 1 H-2), 4.93 ppm (m 1 H-8), 2.76 ppm (m 2 H-6), 2.15 ppm (s 3 H-5), 2.05 ppm (s 3 H-11), 1.94 -1.78 ppm (m 2 H-7), 1.25 ppm (d 3 H-9);
C13-NMR (CDCh), 170.55 ppm (s C-10), 137.10 ppm (s C-4), 132.67 ppm (s C-3), 129.87 ppm (s C-2), 121.09 ppm (s C-1), 70.21 ppm (s C-8), 37.41 ppm (s C-7), 23.79 ppm (s C-6), 21.25 ppm (C-11), 19.94 ppm (s C-9), 13.44 ppm (s C-5);C 13 -NMR (CDCl), 170.55 ppm (s C-10), 137.10 ppm (s C-4), 132.67 ppm (s C-3), 129.87 ppm (s C-2), 121.09 ppm (s C- 1), 70.21 ppm (s C-8), 37.41 ppm (s C-7), 23.79 ppm (s C-6), 21.25 ppm (C-11), 19.94 ppm (s C-9), 13.44 ppm ( s C-5);
IR (cm1), 2974.80, 2935.52, 1733.40, 1371.32, 1237.07;IR (cm 1 ), 2974.80, 2935.52, 1733.40, 1371.32, 1237.07;
GC-MS (m/z), 43(18), 45(6), 77(9), 110(11), 111(60), 125(10), 137(100), 152(63), 153(7), 212 (M+ 6).GC-MS (m / z), 43 (18), 45 (6), 77 (9), 110 (11), 111 (60), 125 (10), 137 (100), 152 (63), 153 (7), 212 (M + 6).
Nowy związek, ze względu na cenne walory zapachowe, trwałość zapachową i prostotę otrzymywania, stanowi potencjalny składnik kompozycji zapachowych różnego przeznaczenia.The new compound, due to its valuable aromatic qualities, fragrance stability and ease of preparation, is a potential component of fragrances for various purposes.
Sposób otrzymywania nowej pochodnej tiofenu, octanu 4-(3-metylotiofen-2-ylo)-butan-2-olu o wzorze 1, z wykorzystaniem reakcji redukcji ketonu wodorkiem w środowisku alkoholu oraz reakcji estryfikacji alkoholu bezwodnikiem octowym w środowisku zasadowym, według wynalazku polega na tym, że 4-(3-metylotiofen-2-ylo)-butan-2-on poddaje się reakcji redukcji borowodorkiem sodu w środowisku metanolu w temperaturze 0-5°C w czasie 2 godzin, stosując 0,13 g borowodorku i 5 ml metanolu na 1 g 4-(3-metylotiofen-2-ylo)-butan-2-onu, a otrzymany w tej reakcji 4-(3-metylotiofen-2-ylo)-butan-2-ol, po wyodrębnieniu ze środowiska reakcji, poddaje się reakcji estryfikacji bezwodnikiem octowym w obecności pirydyny w środowisku dichlorometanu w temperaturze 40°C w czasie 1,5 godziny, stosując 1,24 g bezwodnika octowego, 1,2 ml pirydyny, 3 ml dichlorometanu na 1 g 4-(3-metylotiofen-2-ylo)butan-2-olu.The method of obtaining a new thiophene derivative, 4- (3-methylthiophen-2-yl) -butan-2-ol acetate of the formula 1, using the ketone reduction reaction with a hydride in an alcohol environment and the esterification of alcohol with acetic anhydride in an alkaline environment, according to the invention is in that 4- (3-methylthiophen-2-yl) -butan-2-one is reduced with sodium borohydride in methanol at 0-5 ° C for 2 hours using 0.13 g of borohydride and 5 ml of methanol per 1 g of 4- (3-methylthiophen-2-yl) -butan-2-one, and the 4- (3-methylthiophen-2-yl) -butan-2-ol obtained in this reaction, after separation from the medium reaction, subjected to esterification with acetic anhydride in the presence of pyridine in a medium of dichloromethane at the temperature of 40 ° C for 1.5 hours, using 1.24 g of acetic anhydride, 1.2 ml of pyridine, 3 ml of dichloromethane per 1 g of 4- (3 -methylthiophen-2-yl) butan-2-ol.
PL 236 887 Β1PL 236 887 Β1
Produkt estryfikacji, po wyodrębnieniu ze środowiska reakcji, oczyszcza się chromatograficznie.The esterification product, after isolation from the reaction medium, is purified by chromatography.
Przedmiot wynalazku ilustruje poniższy przykład.The following example illustrates the subject of the invention.
PrzykładExample
W zlewce sporządzono roztwór 11,02 g (0,066 mola) 4-(3-metylotiofen-2-ylo)-butan-2-onu w 50 ml alkoholu metylowego, po czym roztwór ten umieszczono w łaźni lodowej i podczas mieszania dodano do niego 1,46 g (0,038 mola) borowodorku sodu. Następnie odparowano na wyparce rotacyjnej alkohol metylowy, pozostałość zakwaszono kwasem solnym do pH ok. 2 i ekstrahowano heksanem (2 porcjami x 50 ml), a następnie przemyto wodą do odczynu obojętnego. Po odparowaniu rozpuszczalnika na wyparce próżniowej otrzymano 9,0 g 4-(3-metylotiofen-2-ylo)-butan-2-olu o czystości chromatograficznej 99%, co stanowiło 81% wydajności teoretycznej. Strukturę związku potwierdziły widma: H1-NMR (CDCb), 7.04 - 6.82 ppm (dd 2 H-1,2), 3.86 ppm (m 1 H-8), 2.85 ppm (m 2 CH2-łańcuch), 2.21 ppm (s 3 H-5), 1.82 ppm (m 2 CH2-łańcuch), 1.28 ppm (dd 3 H-9);A solution of 11.02 g (0.066 mol) of 4- (3-methylthiophen-2-yl) -butan-2-one in 50 ml of methyl alcohol was prepared in a beaker, then this solution was placed in an ice bath and 1 was added with stirring. , 46 g (0.038 mol) of sodium borohydride. Then the methyl alcohol was evaporated on a rotary evaporator, the residue was acidified with hydrochloric acid to a pH of about 2 and extracted with hexane (2 portions x 50 ml), and then washed with water until neutral. After evaporating the solvent in a vacuum evaporator, 9.0 g of 4- (3-methylthiophen-2-yl) -butan-2-ol were obtained with a chromatographic purity of 99%, which was 81% of theory. The structure of the compound was confirmed by the spectra: H 1 -NMR (CDCb), 7.04 - 6.82 ppm (dd 2 H-1.2), 3.86 ppm (m 1 H-8), 2.85 ppm (m 2 CH 2 -chain), 2.21 ppm (s 3 H-5), 1.82 ppm (m 2 CH 2 -chain), 1.28 ppm (dd 3 H-9);
C13-NMR (CDCb), 137.70 ppm (s C-4), 132.40 ppm (s C-3), 129.77 ppm (s C-2), 120.77 ppm (s C-1), 66.99 ppm (s C-8), 40.39 ppm (s C-7), 23.98 ppm (s C-6), 23.32 ppm (s C-9), 13.37 ppm (s C-5);C 13 -NMR (CDCb), 137.70 ppm (s C-4), 132.40 ppm (s C-3), 129.77 ppm (s C-2), 120.77 ppm (s C-1), 66.99 ppm (s C- 8), 40.39 ppm (s C-7), 23.98 ppm (s C-6), 23.32 ppm (s C-9), 13.37 ppm (s C-5);
IR (cm1), 3349.26, 2965.86, 2925.02, 2859.43, 1450.65, 1374.05, 1328.02;IR (cm 1 ), 3349.26, 2965.86, 2925.02, 2859.43, 1450.65, 1374.05, 1328.02;
GC-MS (m/z), 45(19), 77(12), 97(26), 111(100), 112(31), 137(81), 152(14), 170 (M+ 29).GC-MS (m / z), 45 (19), 77 (12), 97 (26), 111 (100), 112 (31), 137 (81), 152 (14), 170 (M + 29) .
W kolbie umieszczono 2 g (0,012 mola) 4-(3-metylotiofen-2-ylo)-butan-2-olu, 2,45 g (0,024 mola) bezwodnika octowego, 2,4 ml pirydyny, 5 ml dichlorometanu i całość ogrzewano do wrzenia przez 1,5 godziny. Po tym czasie dodano 10 ml wody i całość ogrzewano przez 30 minut w temperaturze 70°C, a następnie ekstrahowano produkt dichlorometanem (3 porcjami po 15 ml). Połączone warstwy organiczne przemyto kwasem solnym do całkowitego zaniku zapachu pirydyny. Po przemyciu wodą, osuszeniu i odparowaniu rozpuszczalnika otrzymano 2,12 g octanu 4-(3-metylotiofen-2-ylo)-butan-2-olu o czystości chromatograficznej 99% z wydajnością 83%. Strukturę związku potwierdziły jego dane spektralne.2 g (0.012 mol) of 4- (3-methylthiophen-2-yl) -butan-2-ol, 2.45 g (0.024 mol) acetic anhydride, 2.4 ml of pyridine, 5 ml of dichloromethane were placed in the flask and the mixture was heated. to boil for 1.5 hours. After this time, 10 ml of water was added and the mixture was heated for 30 minutes at 70 ° C and then the product was extracted with dichloromethane (3 portions of 15 ml). The combined organic layers were washed with hydrochloric acid until the pyridine odor disappeared completely. After washing with water, drying and evaporating the solvent, 2.12 g of 4- (3-methylthiophen-2-yl) -butan-2-ol acetate were obtained with a chromatographic purity of 99% in a yield of 83%. The structure of the compound was confirmed by its spectral data.
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| PL422238A PL236887B1 (en) | 2017-07-17 | 2017-07-17 | Derivative of thiophene and method for obtaining it |
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| EP1458705B1 (en) * | 2001-12-19 | 2009-07-22 | Flexitral, Inc. | Thiophene derivatives and their use as fragrants |
| PL228846B1 (en) * | 2015-06-22 | 2018-05-30 | Politechnika Lodzka | Derivative of thiophene and method for obtaining it |
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