公开(公告)号：US3901921A

公开(公告)日：1975-08-26

申请号：US24734272

申请日：1972-04-25

Applicant: COMMERCIAL SOLVENTS CORP

Inventor： URRY WILBERT HERBERT ,  MULLENBACH GUY TOWNS

IPC: C07C45/00 ,  C07C45/51 ,  C07C57/03 ,  C07C309/73 ,  C07D313/00 ,  C07D321/00 ,  C07D7/26 ,  C07D9/00

CPC classification number: C07D321/00 ,  C07C45/004 ,  C07C45/512 ,  C07C45/515 ,  C07C57/03 ,  C07C309/73 ,  C07C403/02 ,  C07C2601/16 ,  C07D313/00 ,  C07C47/21

Abstract: Compounds of the formula

where X is an integer from 0 to 12, are synthesized employing a process involving lactone ring closure of compounds of the formula

D R A W I N G

公开(公告)号：US3903115A

公开(公告)日：1975-09-02

申请号：US44586074

申请日：1974-02-26

Applicant: COMMERCIAL SOLVENTS CORP

Inventor： URRY WILBERT H ,  MULLENBACH GUY TOWNS

IPC: A23K1/16 ,  C07C57/03 ,  C07D9/00

CPC classification number: C07C57/03 ,  A23K20/126 ,  C07C17/093 ,  C07C45/512 ,  C07C45/515 ,  C07C403/02 ,  C07C2601/16 ,  C07C21/14 ,  C07C47/21

Abstract: This invention provides a new synthesis for norzearalane II and related compounds which related compounds and norzearalane II are represented by the formula

where X is an integer having a value from 1 to 13 inclusive. The anabolic agent norzearalane II, in which X 9 in the foregoing formula, is prepared by a total chemical synthesis involving the reaction of 10-undecenal with malonic acid to produce trans-2,12-tridecadienoic acid; treating the acid so formed with diazomethane to yield methyl trans-2,12tridecadienoate; reacting the methyl ester with ethyl acetoacetate and sodium ethoxide to form the sodium salt of ethyl 6-(9-decenyl)- Beta -dihydroresorcylate; brominating the dihydroresorcylate to prepare ethyl 3-bromo-6-(9-decenyl)- Beta dihydroresorcylate; de-hydrobrominating the foregoing bromo derivative to give ethyl 6-(9-decenyl)- Beta -resorcylate; reacting the resorcylate ester with benzyl chloride to produce ethyl 6-(9-decenyl)- Beta -resorcylate dibenzyl ether; subjecting the benzylated ester to the action of diborane, water and hydrogen peroxide to form ethyl 2,4-bis(benzyloxy)-6-(10hydroxydecyl)-benzoate; treating the foregoing benzoate with sodium ethoxide to prepare norzearalane II dibenzyl ether, and also to prepare as a by-product the dimeric dilactone of 2,4bis(benzyloxy)-6-(10-hydroxydecyl)-benzoic acid; hydrogenating norzearalane II dibenzyl ether to form norzearalane II.

Abstract translation: 本发明提供了新月桂酸二异氰酸酯和相关化合物的新合成物，其中相关化合物和犹比达烷II由式OH O | PARALLEL C ANGLE O | CH 2 | ANGLE HO（CH 2）X表示，其中X是具有从1到 13包含

公开(公告)号：US3901922A

公开(公告)日：1975-08-26

申请号：US45540974

申请日：1974-03-27

Applicant: COMMERCIAL SOLVENTS CORP

Inventor： URRY WILBERT HERBERT ,  MULLENBACH GUY TOWNS

IPC: C07C47/21 ,  C07C51/353 ,  C07D9/00

CPC classification number: C07C45/512 ,  C07C47/21 ,  C07C51/353 ,  C07C403/02 ,  C07C2601/16 ,  C07C57/03

Abstract: 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

公开(公告)号：US3862980A

公开(公告)日：1975-01-28

申请号：US24741472

申请日：1972-04-25

Applicant: COMMERCIAL SOLVENTS CORP

Inventor： URRY WILBERT HERBERT ,  MULLENBACH GUY TOWNS

IPC: C07C51/38 ,  C07C69/92 ,  C07D313/00 ,  C07C69/78

CPC classification number: C07C403/02 ,  C07C45/512 ,  C07C51/38 ,  C07C67/00 ,  C07C67/03 ,  C07C67/307 ,  C07C67/31 ,  C07C69/92 ,  C07C2601/16 ,  C07D313/00 ,  C07C47/21 ,  C07C57/03 ,  C07C69/587 ,  C07C69/738 ,  C07C69/73

Abstract: 4-Penten-2-yl 6-(4-pentenyl)- Beta -resorcylate dibenzyl ether useful in preparing zearalone is disclosed. Zearalone is useful in promoting the growth rate of meat producing animals.

Abstract translation: 公开了可用于制备zearalone的4-戊烯-2-基6-（4-戊烯基）-β-间苯二甲酸二苄基醚。 Zearalone有助于促进肉类生产动物的生长速度。