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Optically active ester compounds and application in perfume compositions

A technology of compounds and compositions, applied in the field of optically active ester compounds, capable of solving problems such as unrevealed or proposed chiral centers

Active Publication Date: 2009-11-18
INTERNATIONAL FLAVORS & FRAGRANCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, no other chiral center at carbon 1' has been disclosed or suggested in the art

Method used

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  • Optically active ester compounds and application in perfume compositions
  • Optically active ester compounds and application in perfume compositions
  • Optically active ester compounds and application in perfume compositions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment I

[0049]

[0050] (3,3-Dimethylcyclohexyl) diethyl malonate Malonic acid

[0051] Ethanol (+ / -)(1RS, 1’RS)-1-(3’, 3’-

[0052] Dimethyl-1'-cyclohexyl)ethyl

[0053] ethyl ester

[0054] Preparation of (+ / -)-(1RS,1'RS)-1-(3',3'-dimethyl-1'-cyclohexyl)ethylethyl malonate:

[0055] Malonate (+ / -)-(1RS, 1'RS)-1-(3', 3'-dimethyl-1'-cyclohexyl)ethane was prepared according to the above method disclosed in U.S. Patent No. 6,774,260 ethyl ethyl ester (Formula II). 250 grams of (3,3-dimethylcyclohexyl) ethanol ( IFF) and 1000 g of diethyl malonate (obtained from Aldrich Chemical Company, Inc., Milwaukee, Wisconsin) was heated to 160° C. while distilling off ethanol . Vacuum distillation provided 405 g of product (Formula II).

[0056] The product has a boiling point of 138°C at 3.5 mm Hg. The NMR analysis of the product is as follows: 0.81-1.66ppm (m, 9H); 0.8...

Embodiment II

[0059]

[0060] (+)-(3S)-3,7-bis(+)(1S,1’R)1-(3,3-dimalonic acid

[0061] Methyl-octyl-1,6-dimethylcyclohexyl)ethanol (+)(1S,1’R)-1-(3’,3’-di

[0062] ene methyl-1'-cyclohexyl) ethyl ethyl

[0063] ester

[0064] Preparation of (+)-(1S,1'R)-1-(3',3'-dimethyl-1'-cyclohexyl)ethylethyl malonate:

[0065] First, according to the method described by Ansari, H.R. (Tetrahedron (1973) 29, 1559-1564), from (+)-(3S)-3,7-dimethyl-octa-1,6-diene (available from IFF purchased) to obtain the chiral alcohol (+)-(1S,1'R)-1-(3',3'-dimethylcyclohexyl)ethanol. Following the procedure detailed in Example I, the resulting chiral alcohol was reacted with diethyl malonate to form malonate (+)-(1S,1'R)-1-(3',3' -Dimethyl-1'-cyclohexyl) ethyl ethyl ester (formula III), whose [α] D 25 Optical rotation = +4.6 (c = 1).

[0066] Chiral GC analysis showed the product to be in an enantiomeric excess of 95% ee.

[0067] The compound i...

Embodiment III

[0069]

[0070] (3,3-Dimethylcyclohexyl 1-(3,3-Dimethylcyclohexyl)-(1S,1’RS)-1-(3’,3’-dimethyl

[0071] base) ethanol ethyl ketone (cyclohexyl) ethanol

[0072]

[0073] Malonate

[0074] (+)-(1S, 1’RS)-1-(3’, 3’-Two

[0075] Methyl-1'-cyclohexyl) ethyl ethyl

[0076] ester

[0077] Preparation of (+)-(1S,1'RS)-1-(3',3'-dimethyl-1'-cyclohexyl)ethylethyl malonate:

[0078] Oxidation of (3,3-dimethylcyclohexyl)ethanol to form 1-(3,3-dimethyl-cyclohexyl)-ethanone ( IFF), the compound was then hydrogenated using an asymmetric hydrogenation catalyst (R)Xyl-P-Phos RuCl2(R, R)-DPEN (as described by Chen et al. (Organic Chemistry (J.Org.Chem.) (2002) 67, 7908- 7910) to form (1S, 1'RS)-1-(3', 3'-dimethylcyclohexyl)ethanol. According to the method...

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Abstract

Optically active ester compounds of the formula: in particular, are useful fragrance materials.

Description

technical field [0001] The invention relates to an optically active ester compound and its introduction and application as a fragrance material. Background technique [0002] The study of molecular chirality has become one of the most important fields exploring the research of organic synthesis. The activity of many drugs, fragrances, food regulators and agrochemicals is often related to their chiral configuration. A wrong enantiomeric form of a compound may lack desired biological, physical or chemical properties. In the fragrance industry, there is a constant need to provide new chemicals that enable perfumers and others to create new fragrances for use in perfumes, colognes and personal care products. However, the difficult challenges of identifying chiral centers and developing cost-effective processes to synthesize enantiomers and / or target racemates, not to mention the unpredictability of active form discovery, often result in aroma The effect is stronger than that ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/38C11B9/00
CPCC11B9/0034C07C2101/14C07C69/38C07C2601/14
Inventor A·T·小莱沃斯C·史密斯R·A·维斯
Owner INTERNATIONAL FLAVORS & FRAGRANCES