US2001044407A1PendingUtilityA1

1,2-substituted 2,3-dihydro-1H-5,9-dioxacyclohepta [ f ] inden -7- ones and 7-substituted benzo [ b ] [ 1,4 ] dioxepin -3-ones

48
Priority: Mar 23, 2000Filed: Mar 23, 2001Published: Nov 22, 2001
Est. expiryMar 23, 2020(expired)· nominal 20-yr term from priority
Inventors:Philip Kraft
C11B 9/0084C07D 321/10
48
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Claims

Abstract

The invention relates to 1,2-substituted 2,3-dihydro-1H-5,9-dioxacyclohepta[f]inden-7-ones and 7-substituted benzo[b][1,4]dioxepin-3-ones and to the use of these compounds in fragrance compositions.

Claims

exact text as granted — not AI-modified
What is claimed is:  
     
         1 . A compound of formula I:  
       
         
           
           
               
               
           
         
       
       wherein 
 R 1  is H, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH(CH 3 ) 2 , CH 2 CH 2 CH 2 CH 3 ;  
 R 2  is H, or CH 3 ; and  
 R 3  is H, CH 3 , or CH 2 CH 3 ,  
 and the dashed line is a double bond or a ring closure forming an indane ring system where, in the case of a double bond R 1 ═R 2 ═H, and in all other cases, the total number of carbon atoms of all residues in formula I is given by C 8 >R 1 +R 2 +R 3 >C 1 .  
 
     
     
         2 . A compound according to    claim 1    wherein, when an indane ring system is formed, R 1  or R 2 ═CH 3 .  
     
     
         3 . A compound according to    claim 2    selected from the group consisting of 7-allylbenzo[b][1,4]dioxepin-3-one, 1-methyl-2,3-dihydro-1H-5,9-dioxacyclohepta[f]inden-7-one, 7-(3-methylbutyl)benzo[b][1,4]dioxepin-3-one, 1,1-dimethyl-2,3-dihydro-1H-5,9-dioxacyclohepta[f]inden-7-one, 7-(2-methylbutyl)benzo[b][1,4]dioxepin-3-one, 7-pentylbenzo[b][1,4]dioxepin-3-one, 1,2-dimethyl-2,3-dihydro-1H-5,9-dioxacyclohepta[f]inden-7-one, 7-hexylbenzo[b][1,4]dioxepin-3-one, 7-(3-methyl-pentyl)benzo[b][1,4]dioxepin-3-one, 7-(2-ethylbutyl)-benzo[b][1,4]dioxepin-3-one, and 7-heptylbenzo[b][1,4]-dioxepin-3-one.  
     
     
         4 . A compound as claimed in    claim 3    selected from the group consisting of 7-allylbenzo[b][1,4]dioxepin-3-one, 1-methyl-2,3-dihydro-1H-5,9-dioxacyclohepta[f]inden-7-one, 7-(3-methylbutyl)benzo[b][1,4]dioxepin-3-one, 1,1-dimethyl-2,3-dihydro-1H-5,9-dioxacyclohepta[f]inden-7-one, 7-(2-methylbutyl)benzo[b][1,4]dioxepin-3-one, 7-pentylbenzo[b][1,4]dioxepin-3-one, 1,2-dimethyl-2,3-dihydro-1H-5,9-dioxacyclohepta[f]inden-7-one, and 7-hexylbenzo[b][1,4]dioxepin-3-one].  
     
     
         5 . A compound according to    claim 4    selected from the group consisting of 7-allylbenzo[b][1,4]dioxepin-3-one, and 7-(3-methylbutyl)benzo[b][1,4]dioxepine-3-one.  
     
     
         6 . A fragrance composition comprising at least one compound of formula I:  
       
         
           
           
               
               
           
         
       
       wherein 
 R 1  is H, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH(CH 3 )  2 , CH 2 CH 2 CH 2 CH 3 ;  
 R 2  is H, or CH 3 ; and  
 R 3  is H, CH 3 , or CH 2 CH 3 ,  
 and the dashed line is a double bond or a ring closure forming an indane ring system where, in the case of a double bond R 1 ═R 2 ═H, and in all other cases, the total number of carbon atoms of all residues in formula I is given by C 8 >R 1 +R 2 +R 3 >C 1 .  
 
     
     
         7 . A fragrance composition according to    claim 6    wherein the compound of formula I is selected from the group consisting of 7-allylbenzo[b][1,4]dioxepin-3-one, 1-methyl-2,3-dihydro-1H-5,9-dioxacyclohepta[f]inden-7-one, 7-(3-methylbutyl)benzo[b][1,4]dioxepin-3-one, 1,1-dimethyl-2,3-dihydro-1H-5,9-dioxacyclohepta[f]inden-7-one, 7-(2-methylbutyl)benzo[b][1,4]dioxepin-3-one, 7-pentylbenzo[b][1,4]dioxepin-3-one, 1,2-dimethyl-2,3-dihydro-1H-5,9-dioxacyclohepta[f]inden-7-one, 7-hexylbenzo[b][1,4]dioxepin-3-one, 7-(3-methyl-pentyl)benzo[b][1,4]dioxepin-3-one, 7-(2-ethylbutyl)-benzo[b][1,4]dioxepin-3-one, 7-heptylbenzo[b][1,4]-dioxepin-3-one, and mixtures thereof.  
     
     
         8 . A fragrance composition according to    claim 7    wherein the compound of formula I is selected from the group consisting of 7-allylbenzo[b][1,4]dioxepin-3-one, 1-methyl-2,3-dihydro-1H-5,9-dioxacyclohepta[f]inden-7-one, 7-(3-methylbutyl)benzo[b][1,4]dioxepin-3-one, 1,1-dimethyl-2,3-dihydro-1H-5,9-dioxacyclohepta[f]inden-7-one, 7-(2-methylbutyl)benzo[b][1,4]dioxepin-3-one, 7-pentylbenzo[b][1,4]dioxepin-3-one, 1,2-dimethyl-2,3-dihydro-1H-5,9-dioxacyclohepta[f]inden-7-one, 7-hexylbenzo[b][1,4]dioxepin-3-one], and mixtures thereof.  
     
     
         9 . A fragrance composition according to    claim 8    wherein the compound of formula I is selected from the group consisting of 7-allylbenzo[b][1,4]dioxepin-3-one, 7-(3-methylbutyl)benzo[b][1,4]dioxepine-3-one, and mixtures thereof.  
     
     
         10 . A method for providing a fragrance comprising: 
 applying to a substrate a fragrance composition comprising at least one compound of formula I:                          wherein    R 1  is H, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH(CH 3 ) 2 , CH 2 CH 2 CH 2 CH 3 ;    R 2  is H, or CH 3 ; and    R 3  is H, CH 3 , or CH 2 CH 3 ,    and the dashed line is a double bond or a ring closure forming an indane ring system where, in the case of a double bond R 1 ═R 2 ═H, and in all other cases, the total number of carbon atoms of all residues in formula I is given by C 8 >R 1 +R 2 +R 3 >C 1 .    
     
     
         11 . A method according to    claim 10    wherein the compound of formula I is selected from the group consisting of 7-allylbenzo[b][1,4]dioxepin-3-one, 1-methyl-2,3-dihydro-1H-5,9-dioxacyclohepta[f]inden-7-one, 7-(3-methylbutyl)benzo[b][1,4]dioxepin-3-one, 1,1-dimethyl-2,3-dihydro-1H-5,9-dioxacyclohepta[f]inden-7-one, 7-(2-methylbutyl)benzo[b][1,4]dioxepin-3-one, 7-pentylbenzo[b][1,4]dioxepin-3-one, 1,2-dimethyl-2,3-dihydro-1H-5,9-dioxacyclohepta[f]inden-7-one, 7-hexylbenzo[b][1,4]dioxepin-3-one, 7-(3-methyl-pentyl)benzo[b][1,4]dioxepin-3-one, 7-(2-ethylbutyl)-benzo[b][1,4]dioxepin-3-one, 7-heptylbenzo[b][1,4]-dioxepin-3-one, and mixtures thereof.  
     
     
         12 . A method according to    claim 11    wherein the compound of formula I is selected from the group consisting of 7-allylbenzo[b][1,4]dioxepin-3-one, 1-methyl-2,3-dihydro-1H-5,9-dioxacyclohepta[f]inden-7-one, 7-(3-methylbutyl)benzo[b][1,4]dioxepin-3-one, 1,1-dimethyl-2,3-dihydro-1H-5,9-dioxacyclohepta[f]inden-7-one, 7-(2-methylbutyl)benzo[b][1,4]dioxepin-3-one, 7-pentylbenzo[b][1,4]dioxepin-3-one, 1,2-dimethyl-2,3-dihydro-1H-5,9-dioxacyclohepta[f]inden-7-one, 7-hexylbenzo[b][1,4]dioxepin-3-one], and mixtures thereof.  
     
     
         13 . A method according to    claim 12    wherein the compound of formula I is selected from the group consisting of 7-allylbenzo[b][1,4]dioxepin-3-one, 7-(3-methylbutyl)benzo[b][1,4]dioxepine-3-one, and mixtures thereof.

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