Process for preparation of MK-7 type of vitamin K2 is characterized by attaching hexaprenyl chain of “all-trans” configuration to monoprenyl derivative of menadiol following “1+6” synthetic strategy. According to the invention, a-sulfonyl carbanion generated in situ from the protected monoprenyl menadiol of the formula (II), wherein R.sub.1 represents C.sub.1-3-alkyl group, is reacted with hexaprenyl halide of the formula (VII), wherein X represents halogen atom, preferably bromine, both Z′ and Z′ represent H or one of Z′ and Z″ represents H and the other represents phenylsulfonyl group —SO.sub.2Ph in the alkylation reaction. The hexaprenyl halide of formula (VII) is obtained by coupling two triprenyl units in alkylation reaction, with or without separation of the intermediates. ##STR00001##

Process for preparation of MK-7 type of vitamin K2 is characterized by attaching hexaprenyl chain of “all-trans” configuration to monoprenyl derivative of menadiol following “1+6” synthetic strategy. According to the invention, a-sulfonyl carbanion generated in situ from the protected monoprenyl menadiol of the formula (II), wherein R.sub.1 represents C.sub.1-3-alkyl group, is reacted with hexaprenyl halide of the formula (VII), wherein X represents halogen atom, preferably bromine, both Z′ and Z′ represent H or one of Z′ and Z″ represents H and the other represents phenylsulfonyl group —SO.sub.2Ph in the alkylation reaction. The hexaprenyl halide of formula (VII) is obtained by coupling two triprenyl units in alkylation reaction, with or without separation of the intermediates. ##STR00001##

A process of converting a carbon-carbon multiple bond to a cyclopropane ring, comprising the addition of a N-alkyl-N-nitroso compound to a mixture of alkene precursor, aqueous base and Pd(II)-catalyst, with the N-alkyl-N-nitroso compound obtained directly from an alkyl amine derivative, NaNO.sub.2 and an acid via phase separation of the N-alkyl-N-nitroso compound from the aqueous phase.

A process of converting a carbon-carbon multiple bond to a cyclopropane ring, comprising the addition of a N-alkyl-N-nitroso compound to a mixture of alkene precursor, aqueous base and Pd(II)-catalyst, with the N-alkyl-N-nitroso compound obtained directly from an alkyl amine derivative, NaNO.sub.2 and an acid via phase separation of the N-alkyl-N-nitroso compound from the aqueous phase.

Compounds of formula (I) in the form of any one of its stereoisomers or a mixture thereof are provided, wherein the dotted lines represent a carbon-carbon single bond or a carbon-carbon double bond; and one R.sup.1 group represents a hydrogen atom and the second R.sup.1 group represents a methyl group. Also provided are their uses as perfuming ingredients to impart vetiver/rooty and powdery notes; e.g. in perfuming compositions or in consumer products. ##STR00001##

Compounds of formula (I) in the form of any one of its stereoisomers or a mixture thereof are provided, wherein the dotted lines represent a carbon-carbon single bond or a carbon-carbon double bond; and one R.sup.1 group represents a hydrogen atom and the second R.sup.1 group represents a methyl group. Also provided are their uses as perfuming ingredients to impart vetiver/rooty and powdery notes; e.g. in perfuming compositions or in consumer products. ##STR00001##

Provided is an application of a metal hydride/palladium compound system in the preparation of a 1,3-dicarbonyl compound in a cascade reaction of an electron-deficient alkene compound, said reaction comprising the following steps: under the protection of nitrogen, a palladium compound and a metal hydride are suspended and stirred in a solvent, then an electron-deficient alkene compound is added; the mixture reacts at 0° C. to 100° C. for 0.3 to 10 hours; a saturated ammonium chloride aqueous solution is added to stop the reaction, and then extraction, drying by evaporation and purification by column chromatography are performed to obtain the product of 1,3-dicarbonyl compound. The hydride and palladium compound catalysts used in the method are reagents easily obtained in a laboratory; compared with the commonly used methods of hydrogenation with hydrogen gas, the method can be easily operated, and has high safety, mild conditions and high reaction yield.

Provided is an application of a metal hydride/palladium compound system in the preparation of a 1,3-dicarbonyl compound in a cascade reaction of an electron-deficient alkene compound, said reaction comprising the following steps: under the protection of nitrogen, a palladium compound and a metal hydride are suspended and stirred in a solvent, then an electron-deficient alkene compound is added; the mixture reacts at 0° C. to 100° C. for 0.3 to 10 hours; a saturated ammonium chloride aqueous solution is added to stop the reaction, and then extraction, drying by evaporation and purification by column chromatography are performed to obtain the product of 1,3-dicarbonyl compound. The hydride and palladium compound catalysts used in the method are reagents easily obtained in a laboratory; compared with the commonly used methods of hydrogenation with hydrogen gas, the method can be easily operated, and has high safety, mild conditions and high reaction yield.

The present invention relates to bi- and tricyclic compounds of the general formula (I) (I) wherein the dashed lines independently of each other represent a single or a double bond, X represents a group of the formulae X.sub.1 to X.sub.3 wherein the asterisk denotes the point of attachment to the rest of the molecule, R.sup.1a and R.sup.1b, independently of each other, are selected from hydrogen or methyl, or R.sup.1a together with R.sup.1b with R form a methylene or ethylene group, R.sup.2, R.sup.3a, R.sup.3b, R.sup.4, R.sup.5a and R.sup.5b, independently of each other, are selected from hydrogen or methyl, R.sup.6 is selected from hydrogen, methyl or ethyl, and R.sup.7 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.

##STR00001##

The present invention relates to bi- and tricyclic compounds of the general formula (I) (I) wherein the dashed lines independently of each other represent a single or a double bond, X represents a group of the formulae X.sub.1 to X.sub.3 wherein the asterisk denotes the point of attachment to the rest of the molecule, R.sup.1a and R.sup.1b, independently of each other, are selected from hydrogen or methyl, or R.sup.1a together with R.sup.1b with R form a methylene or ethylene group, R.sup.2, R.sup.3a, R.sup.3b, R.sup.4, R.sup.5a and R.sup.5b, independently of each other, are selected from hydrogen or methyl, R.sup.6 is selected from hydrogen, methyl or ethyl, and R.sup.7 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.

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