公开(公告)号：US3852307A

公开(公告)日：1974-12-03

申请号：US24734372

申请日：1972-04-25

Applicant: COMMERCIAL SOLVENTS CORP

Inventor： URRY W ,  MULLENBACH G

IPC: C07C51/295 ,  C07C57/03 ,  C07C57/66 ,  C07D313/00 ,  C07D317/30 ,  C07D9/00 ,  C07D7/20

CPC classification number: C07C403/16 ,  C07C51/295 ,  C07C57/03 ,  C07C57/66 ,  C07C2601/14 ,  C07D313/00 ,  C07D317/30 ,  C07C59/76

Abstract: 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

Abstract translation: 本发明提供了一种新的Zearalanone合成物，以及在非芳族环中具有或多于少于碳原子的相关化合物的合成相对于Zearalanone，该相关化合物和泽西拉酮由式WHEREIN X表示为0至6的整数 Y为包含3〜8的整数。 它还提供了制备化合物的新方法，可用于合成泽西拉酮及其相关化合物。

公开(公告)号：US3836544A

公开(公告)日：1974-09-17

申请号：US24728272

申请日：1972-04-25

Applicant: COMMERCIAL SOLVENTS CORP

Inventor： URRY W ,  MULLENBACH G

IPC: A23K1/16 ,  C07C17/093 ,  C07C51/353 ,  C07C57/03 ,  C07D313/00 ,  C07D315/00 ,  C07D321/00 ,  C07D9/00

CPC classification number: C07D321/00 ,  A23K20/126 ,  C07C17/093 ,  C07C45/512 ,  C07C45/515 ,  C07C51/353 ,  C07C57/03 ,  C07C403/02 ,  C07C2601/16 ,  C07D313/00 ,  C07C21/14 ,  C07C47/21 ,  C07C57/00

Abstract: THIS INVENTION PROVIDES A NEW SYNTHESIS FOR NORZEARALANE II AND RELATED COMPOUNDS WHICH RELATED COMPOUNDS AND NORZEARALANE II ARE REPRESENTED BY THE FORMULA

1,5-DI(HO-),2,3-(-CO-O-CH2-(CH2)X-)-BENZENE

WHERE X IS AN INTEGER HAVING A VALUE FROM 1 TO 13 INCLUSIVE. THE ANABOLIC AGENT NORZEARALANE II, IN WHICH X=9 IN THEFOREGOING 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 DIAZOMSTHANE TO YIELD METHYL TRANS-2,12-TRIDECADIENOATE; REACTING THE METHYL ESTER WITH ETHYL ACETOACETATE AND SODIUM ETHOXIDE TO FORM THE SODIUM SALT OF ETHYL 6-(9-DECENYL)-B-DIHYDRORESORCYLATE; BROMINATING THE DIHYDRORESORCYLATE TO PREPARE ETHYL 3-BROMO- 6 - (9-DECENYL)-B-DIHYDRORESOCRYLATE; DE-HYDROBROMINATING THE FOREGOING BROMO DERIVATIVE TO GIVE ETHYL 6-(9-DECENYL)-B-RESORCYLATE; REACTING THE RESORCYLATE ESTER WITH BENZYL CHLORIDE TO PRODUCE ETHYL 6-(9-DECENYL)-BRESORCYLATE DIBENZYL ETHER; SUBJECTING THE BENZYLATED ESTER TO THE ACTION OF DIBORANE, WATER AND HYDROGEN PEROXIDE TO FORM ETHYL 2,4-BIS (BENZYLOXY)-6-(10-HYDROXYDECYL)BENZOATE; TREATING THE FOREGOING BENZOATE WITH SODIUM ETHOXIDE TO PREPARE NORZEARALANE II DIBENZYL ETHER, ONE ALSO TO PREPARE AS A BY-PRODUCT THE DIMERIC DILACTONE OF 2,4-BIS(BENZYLOXY)-6-(10-HYDROXYDECYL)-BENZOIC ACID; HYDROGENATING NORZEARALANE II DIBENZYL ETHER TO FORM NORZEARALANE II. IN GENERAL, A HOMOLOGUE OF NORZEARALANE II AND/OR OF THE CORRESPONDING DIMERIC DILACTONE IS PREPARED BY SUBSTITUTING FOOR 10-UNDECENAL IN THE FOREGOING SEQUENCE OF REACTIONS AN UNSATURATED ALDEHYDE HAVING THE FORMULA

CH2=CH-(CH2)X-1-CHO

WHERE X IS AN INTEGER WHICH MAY HAVE THE VALUE 1,2,3,4, 5, 6, 7, 8, 9, 10, 11, 12 OR 13 SPECIFICALLY ZEARALANE II (WHERE X=10) IS PREPARED STARTING WITH 11-DODECENAL AND THE DIMERIC DILACTONE FROM 6-(5-HYDROXYPENTYL-B-RESORCYCLIC ACID DIBENZYL ETHER IS PREPARED WHEN THE STARTING ALDEHYDE IS 5-HEXENAL (WHERE X= 4) THE INVENTION ALSO COVERS PHYSIOLOGICALLY ACTIVE COMPOUNDS RELATED TO THE ZEARALANES II AND KNOW AS DIMERIC DILACTONES HAVING THE FORMULA,

1,5-DI(RO-),2,3-(-CO-O-CH2-(CH2)X-(3,5-DI(RO-)-1,6-PHENYL

ENE)-CO-O-CH2-(CH2)X-)-BENZENE

X IS AN INTEGER WHICH MAY HAVE THE VALUE 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 OR 13 AND WHERE R IS EITHE HYDROGEN OR A BENZYL RADICAL (C6H5CH2-). MORE PARTICULARLY, THIS INVENTION RELATES TO NOVEL INTERMEDIATES PRODUCED IN THE SYNTHESIS OF THE ABOVE COMPOUNDS AND TO PROCESSES FOR MAKING THESE INTERMEDIATES.

公开(公告)号：US3764614A

公开(公告)日：1973-10-09

申请号：US3764614D

申请日：1970-02-16

Applicant: COMMERCIAL SOLVENTS CORP

Inventor： WEHRMEISTER H ,  URRY W

IPC: A23K1/16 ,  A23K1/18 ,  C07D313/00 ,  C07D9/00

CPC classification number: C07D313/00 ,  A23K20/126 ,  A23K50/30

Abstract: New compounds are provided and have the formula

WHERE B is

R and R'' can be hydrogen, alkyl, acyl or aralkyl radicals; and X and Y are hydrogen or chlorine and at least one of X and Y is chlorine. These compounds exhibit antibacterial activity and can be used in animal feed compositions.

Abstract translation: 提供新的化合物，其结构式为WHERE B是R，R'可以是氢，烷基，酰基或芳烷基; X和Y是氢或氯，X和Y中的至少一个是氯。 这些化合物表现出抗菌活性并可用于动物饲料组合物。