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Bi- and tricyclic compounds for use as aroma chemicals

A technology of compounds, mixtures, applied to bicyclic and tricyclic ketones, to prepare polymerizable compounds, to prepare said compounds, with the aim, in the field of fragrances, to be able to solve substances, organoleptic properties that do not know whether odor and/or taste are actually found Changes, difficulty finding new flavors and seasonings, etc.

Pending Publication Date: 2021-08-20
BASF SE +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, it is extremely difficult to purposefully seek substances with specific sensory properties such as specific odors because even small changes in chemical structure lead to significant changes in sensory properties such as odor and taste
So, in most cases, the search for new flavors and seasonings is difficult and laborious, and it is not even known whether a substance with the desired smell and / or taste has actually been found

Method used

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  • Bi- and tricyclic compounds for use as aroma chemicals
  • Bi- and tricyclic compounds for use as aroma chemicals
  • Bi- and tricyclic compounds for use as aroma chemicals

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0363] abbreviation

[0364] GC: gas chromatography

[0365] MTBE: methyl tert-butyl ether

[0366] EtOAc: ethyl acetate

[0367] analyze:

[0368] Through GC, 1 H-NMR (CDCl 3 ,500MHz) and / or 13 C-NMR (125MHz, CDCl 3 ) to determine the purity and identity of the product.

[0369] 1. Preparation Example

[0370] 1.1 Preparation of 1-((2R)-2,6,7-trimethyl-1,3,4,5,8,8a-hexahydronaphthalene-4a(2H)-yl)ethan-1-one:

[0371] In a 500 mL three-necked round bottom flask equipped with a thermometer and a 250 mL dropping funnel, combine 15 g (108.5 mmol) of 1-[(4R)-4-methylcyclohexen-1-yl]ethanone with AlCl 3 (1.5g) and toluene (200mL). A solution of 2,3-dimethyl-1,3-butadiene (18.2 g, 221.6 mmol) in toluene (100 mL) was added slowly via the dropping funnel over 4 hours. The reaction was stirred at room temperature for an additional 48 hours. Water (100 mL) was added to the reaction mixture to quench the reaction, and acetic acid (50%) was added until all gel-like materi...

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Abstract

The present invention relates to bi-and tricyclic compounds of the general formula (I), wherein the dashed lines independently of each other represent a single or a double bond, X represents a group of the formulae X1 to X3 wherein the asterisk denotes the point of attachment to the rest of the molecule, R1a and R1b, independently of each other, are selected from hydrogen or methyl, or R1a together with R1b form a methylene or ethylene group, R2, R3a, R3b, R4, R5a and R5b, independently of each other, are selected from hydrogen or methyl, R6 is selected from hydrogen, methyl or ethyl, and R7 is methyl or ethyl, to a method of preparing said compounds, to the use of a bi- or tricyclic compounds or of mixtures of two or more bi- and tricyclic compounds or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof as aroma chemicals; to the use of a bi- or tricyclic compound for modifying the scent character of a fragranced composition; to an aroma chemical composition containing a bi- or tricyclic compound or a mixture of two or more bi- and tricyclic compounds or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof; and to a method of preparing a fragranced composition or for modifying the scent character of a fragranced composition, comprising incorporating a bi- or tricyclic compound or a mixture of two or more bi- and tricyclic compounds or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof into said composition.

Description

[0001] The present invention relates to bicyclic and tricyclic compounds of formula (I) described herein, especially to bicyclic and tricyclic ketones; to processes for the preparation of said compounds; to bicyclic or tricyclic compounds, or to two or more bicyclic and tricyclic ketones; Use of mixtures of tricyclic compounds, or stereoisomers thereof, or mixtures of two or more stereoisomers thereof as aroma chemicals; use of said bicyclic or tricyclic compounds for improving aromatic compositions Use of aroma characteristics; relates to aroma chemical compositions containing bicyclic or tricyclic compounds, or mixtures of two or more bicyclic and tricyclic compounds, or stereoisomers thereof, or two or more of their Mixtures of stereoisomers; and methods relating to the preparation of fragrance compositions or improving the aroma profile of fragrance compositions comprising said bicyclic or tricyclic compounds, or mixtures of two or more bicyclic and tricyclic compounds, or A...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/313C07C49/553
CPCC07C49/313C07C49/553C07C2602/28C07C2603/68C07C49/323
Inventor R·派尔泽Y·杨P·弗雷
Owner BASF SE
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