专利号:US-3901922-A 优先权日:1972-04-25 标题 :Synthesis of zearalanone and related compounds and intermediates useful in their synthesis 发明人:URRY WILBERT HERBERT; MULLENBACH GUY TOWNS 权利人:COMMERCIAL SOLVENTS CORP 摘要:WHEREIN X is an integer having a value from 2 to 6 inclusive and Y is an integer having a value from 2 to 8 inclusive. It also provides for new methods of making compounds useful in the synthesis of zearalanone and related compounds. The new compounds useful as intermediates are 2,7-octadienoic acid; methyl 2,7-octadienoate; sodium ethyl 6-(4-pentenyl)- Beta -dihydroesorcylate; ethyl 6-(4-pentenyl)- Beta dihydroresorcylate; sodium methyl 6-(4-pentenyl)- Beta dihydroresorcylate; methyl 6-(4-pentenyl)- Beta dihydroresorcylate; methyl 3-bromo-6-(4-pentenyl)- Beta dihydroresorcylate; methyl 6-(4-pentenyl)- Beta -resorcylate; ethyl 6-(4-pentenyl)- Beta -resorcylate; ethyl 6-(4-pentenyl)Beta -resorcylate dibenzyl ether; tetrahydropyran-2-yl 4-penten2-yl ether; ethyl 6-(6-oxo-10-tetrahydropyran-2-xyloxyundecyl)Beta -resorcylate dibenzyl ether; and 6-(10-hydroxy-6oxounderyl)- Beta -resorcylic acid dibenzyl ether. Methods for preparing these intermediates are also disclosed. This invention provides a new synthesis for zearalanone and for related compounds having more or fewer carbon atoms in the nonaromatic ring than does zearalanone, which related compounds and zearalanone are represented by the formula
专利号:US-3852307-A 优先权日:1972-04-25 标 题 :Synthesis of zearalanone and related compounds 发明人:URRY W; MULLENBACH G 权利人:COMMERCIAL SOLVENTS CORP 摘要:WHEREIN X is an integer having a value from 0 to 6 inclusive and Y is an integer having a value from 3 to 8 inclusive. It also provides for new methods of making compounds useful in the synthesis of zearalanone and related compounds. The compounds 6-acetoxyhexanoic acid; 2-(5-hexenoyl)cyclohexanone; 7-keto-11-dodecenoic acid; 2-hydroxyethyl 7-keto11-dodecenoate ethylene ketal; N,N-dimethyl 7-keto-11dodecenamide ethylene ketal; 7-keto-11-dodecenal ethylene ketal; 9-keto-2,13-tetradecadienic acid ethylene ketal; 2-hydroxyethyl 9-keto-2,13-tetradecadienoate ethylene ketal; the sodium salt of ethyl 6-(6-keto-10-undecenyl)- Beta -dihydroresorcylate ethylene ketal; ethyl 3-bromo-6-(6-keto-10-undecenyl)- Beta dihydroresorcylate ethylene ketal; ethyl 6-(6-keto-10-undecenyl)Beta -resorcylate ehtylene ketal; ethyl 6-(6-keto-10-undecenyl)Beta -resorcylate ethylene ketal dibenzyl ether; ethyl 6-(6keto-10-hydroxyundecyl)- Beta -resorcylate ethylene ketal dibenzyl ether; and 6-(10-hydroxy-6-keto-undecyl)- Beta resorcylic acid dibenzyl ether are disclosed. Methods for preparing these compounds are also disclosed. This invention provides a new synthesis for zearalanone and for related compounds having more or fewer carbon atoms in the nonaromatic ring than does zearalanone, which related compounds and zearalanone are represented by the formula
专利号:US-3810918-A 优先权日:1972-04-25 标题:Synthesis of zearalanone 发明人:URRY W; MULLENBACH G 权利人:COMMERCIAL SOLVENT CORP 摘要:4,5-(-COO-CH(-CH3)-(CH2)X-CO-(CH2)Y-)RESORCINOL THIS INVENTION PROVIDES A NEW SYNTHESIS FOR ZEARALANONE AND FOR RELATED COMPOUNDS HAVING MORE OR FEWER CARBON ATOMS IN THE NON-AROMATIC RING THAN DOES ZEARLANONE, WHICH RELATED COMPOUNDS AND ZEARALANONE ARE REPRESENTED BY THE FORMULA WHEREIN X IS AN INTEGER HAVING A VALUE FROM 2 TO 6 INCLUSIVE AND Y IS AN INTEGER HAVING A VALUE FROM 2 TO 8 INCLUSIVE. IT ALSO PROVIDES FOR NEW METHODS FOR MAKING COMPOUNDS USEFUL IN THE SYNTHESIS OF ZEARALANONE AND RELATED COMPOUNDS. THE NEW COMPOUNDS USEFUL AS INTERMEDIATES ARE 2,7-OCTADIENOIC ACID; METHYL 2,7-OCTADIENOATE; SODIUM ETHYL 6-(4-PENTENYL-B-DIHYDRORESORCYLATE; ETHYL 6-(4-PENTENYL)-B-DIHYDRORESORCYLATE; SODIUM METHYL 6-(4-PENTENYL)-B-DIHYDRORESORCYLATE; METHYL 6-(4-PENTENYL)-B-DIHYDRORESORCYLATE; METHYL 3-BROMO-6(4-PENTENYL)-B-DIHYDRORESORCYLATE; METHYL6-(4-PENTENYL9-B-RESORCYLATE; ETHYL 6-(4-PENTENYL)-B-RESORCYLATE; ETHYL 6-(4-PENTENYL)-B-R-RESORCYLATE DIBENZYL ESTER; TETRAHYDROJPYRAN-2-YL 4-YL 4-PENTEN-2-YL ETHER; ETHYL 6-(6-OXO-10-TETRAHYDROPYRAN-2-XYLOXYUNDECYL)-BRESORCYLATE DIBENZYL ETHER; AND 6-(10-HYDROXY-6-OXOUNDECYL)-B-RESORCYLIC ACID DIBENZYL ETHER. METHODS FOR PREPARING THESE INTERMEDIATES ARE ALSO DISCLOSED.
专利号:US-3839363-A 优先权日:1972-04-25 标 题:Synthesis of zearalanone and related compounds and intermediates useful in the synthesis thereof 发明人:SHAH D; HURD R 权利人:COMMERCIAL SOLVENTS CORP 摘要:1. A COMPOUND OF THE FORMULA 1-(O=),3-(C6H5-CH2-O-(CH2)N0-),4-(CH3-OOC-),- 6,8-DI(R''-O-)ISOCHROMAN WHEREIN NO IS AN INTEGER HAVING THE VALUE 1,2,3,4,5 OR 6 AND R'' IS SELECTED FROM THE GROUP CONSISTING OF BENZYL, METHYL, ETHYL, BUTYL, CYCLOPENTYL, AND CYCLOHEXYL.
专利号:US-3704249-A 优先权日:1969-05-01 标题:Synthesis of the biologically active diastereoisomer of (-) zearalanol 发明人:CZAJA ROBERT F; GRENDA VICTOR J; CHAMBERLIN EARL M 权利人:MERCK & CO INC 摘要:THE ACTIVE GROWTH FACTOR DIASTEREOISOMER OF 6-(6,10DIHYDROXY - UNDECYL) - B - RESORCYLIC ACID - U - LACTONE OR (-) ZEARALANOL IS PREPARED BY STEREOSPECIFIC REDUCTION OF THE CARBONYL MOIETY OF ZEARALANONE, ZEARALENONE, AND DIETHER DERIVATIVES THEREOF.
专利号:US-3957825-A 优先权日:1972-04-25 标 题 :Process for synthesizing zearalanone and related compounds 发明人:URRY WILBERT HERBERT; MULLENBACH GUY TOWNS 权利人:COMMERCIAL SOLVENTS CORP 摘要:This invention provides a new synthesis for zearalanone and for related compounds having more or fewer carbon atoms in the non-aromatic ring than does zearalanone, which related compounds and zearalanone are represented by the formula ##SPC1## n Wherein X is an integer having a value from 2 to 6 inclusive and Y is an integer having a value from 2 to 8 inclusive. It also provides for new methods of making compounds useful in the synthesis of zearalanone and related compounds. n The new compounds useful as intermediates are 2,7-octadienoic acid; methyl 2,7-octadienoate; sodium ethyl 6-(4-pentenyl)-β-dihydroresorcylate; ethyl 6-(4-pentenyl)-β-dihydroresorcylate; sodium methyl 6-(4-pentenyl)-β-dihydroresorcylate; methyl 6-(4-pentenyl)-β-dihydroresorcylate; methyl 3-bromo-6-(4-pentenyl)-β-dihydroresorcylate; methyl 6-(4-pentenyl)-β-resorcylate; ethyl 6-(4-pentenyl)-β-resorcylate; ethyl 6-(4-pentenyl)-β-resorcylate dibenzyl ether; and 4-penten-2-yl 6-(4-pentenyl)-β-resorcylate dibenzyl ether.
1: Faisal Z, Vörös V, Fliszár-Nyúl E, Lemli B, Kunsági-Máté S, Poór M. Interactions of zearalanone, α-zearalanol, β-zearalanol, zearalenone-14-sulfate, and zearalenone-14-glucoside with serum albumin. Mycotoxin Res. 2020 Nov;36(4):389-397. doi: 10.1007/s12550-020-00404-w. Epub 2020 Aug 1. 2: Wu Z, Jiang X, Yang Y, Shi R, Ruan G, Huang Y. Amphiphilic polymers facilitated solid-phase extraction coupled with ultra-performance liquid chromatography-tandem mass spectrometry for direct extraction and analysis of zearalenone and zearalanone in corn juice samples. J Sep Sci. 2023 Jul;46(14):e2300112. doi: 10.1002/jssc.202300112. Epub 2023 May 9. 89(18):13800-13805. doi: 10.1021/acs.joc.4c01793. Epub 2024 Sep 10. 7:583-595. doi: 10.1016/j.toxrep.2020.04.010.
合成参考文献
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