Takasago International Corporation

Kaneka Corporation

Takaji Matsumoto

Takashi Miura

Toshiyuki Murayama

Hisanori Itoh

Makoto Harada

Masashi Otsuka

Tomoharu Sato

Wataru Kuriyama

Osamu Ogata

Kenji Inoue

Noboru Sayo

Takao Saito

Yoji Hori

Ryoji Noyori

Shigeru Mitsuhashi

Tsukasa Sotoguchi

Susumu Saito

Yasunori Ino

Motonobu Takenaka

Hirofumi Maeda

Izuru Nagasaki

Masaya Otake

A lactone compound is represented by general formula (A), and an ether compound is represented by general formula (B). In formula (A), R is a hydrogen atom or R1. When R is a hydrogen atom, R' is R1, the carbon bond (1) is a single bond or a double bond, and the carbon bond (2) is a single bond. When R is R1, R&#x2032; is a hydrogen atom or R1, both the carbon bonds (1) and (2) are a single bond, or one of them is a double bond and the other is a single bond. In formula (B), R&#x2033; is R1. R1 represents a specific alkyl group, a specific alkenyl group, a specific alkynyl group, or an aryl group. In formulas (A) and (B), n is 0 or 1. 

Lactone compound and novel ether compound

A cooling agent composition contains a 2,2,6-trimethylcyclohexanecarboxylic acid derivative represented by the following general formula (1). The symbol * represents an asymmetric carbon atom. X represents NH, N(ZAr), O or S, Z represents a single bond or an alkylene group having 1 to 3 carbon atoms which may have a substituent, Arrepresents an aryl group having 6 to 20 carbon atoms which may have a substituent or an aromatic heterocyclic group having 2 to 15 carbon atoms which may have a substituent. Y each independently represents a methylene group which may have a substituent, and n represents an integer of 0 to 3. Arrepresents an aryl group having 6 to 20 carbon atoms which may have a substituent or an aromatic heterocyclic group having 2 to 15 carbon atoms which may have a substituent. 

Cool-sensation imparter composition containing 2,2,6-trimethylcyclohexanecarboxylic acid derivative

A cooling agent composition includes a methyl menthol derivative represented by the following general formula (1). In the formula (1), a symbol * indicates an asymmetric carbon atom, X represents a hydrogen atom or a substituent, and Y represents an aryl group having 6 to 20 carbon atoms which may have a substituent. 

Methylmenthol derivative and cool-sensation imparter composition containing same

The purpose of the present invention is to provide a cooling agent composition containing a novel methyl menthol derivative having no undesirable feeling of stimulation, malodor, bitterness, or the like, it being possible to use the cooling agent composition as a cooling agent or sensory stimulation agent having exceptional persistence of a sense of coolness and refreshing feeling. The present invention pertains to a cooling agent composition containing a methyl menthol derivative represented by general formula (1A) or general formula (1B). 

Methyl menthol derivative and cooling agent composition containing same

Disclosed herein is a method for producing an alcohol and an amine from an amide under an atmosphere of hydrogen with the use of, as a catalyst, a ruthenium complex that is easily prepared, easy to handle, and relatively cheaply obtained. Specifically, the method is a method for producing an alcohol and/or an amine from an amide compound under an atmosphere of hydrogen with the use of as a catalyst, a ruthenium carbonyl complex represented by the following general formula (1): RuXY(CO)(L) (1) wherein X and Y may be the same or different from each other and each represents an anionic ligand and L represents a tridentate aminodiphosphine ligand containing two phosphino groups and a &#x2014;NH&#x2014; group.

Method for producing alcohol and/or amine from amide compound

The present invention relates to a ruthenium carbonyl complex that is represented by the following Formula (1):RuXY(CO)(L)&#x2003;&#x2003;(1) (in the Formula (1), X and Y, which may be the same or different from each other, represent an anionic ligand and L represents a tridentate aminodiphosphine ligand which has two phosphino groups and a &#x2014;NH&#x2014; group), its production method, and a method for production of alcohols by hydrogenation-reduction of ketones, esters, and lactones using the complex as a catalyst. The ruthenium carbonyl complex of the invention has a high catalytic activity and it can be easily prepared and handled.

Ruthenium carbonyl complex having tridentate ligand, its production method and use

Disclosed is a method for producing an alcohol from a lactone or a carboxylic acid ester, which enables to produce an alcohol from a lactone or a carboxylic acid ester under relatively mild conditions with high yield and high catalytic efficiency. This method also enables to produce an optically active alcohol from an optically active lactone or an optically active carboxylic acid ester. Specifically disclosed is a method for producing an alcohol by hydrogen reducing a lactone or a carboxylic acid ester in the presence of a catalyst containing ruthenium and a phosphine compound represented by the following general formula (1): wherein Rrepresents a spacer; R, R, R, R, Rand Rindependently represent a hydrogen atom, an alkyl group having 1-12 carbon atoms, an aryl group or a heterocyclic group; and R, R, R, R, Rand Rindependently represent an alkyl group having 1-12 carbon atoms, an aryl group or a heterocyclic group.

Method for producing alcohol by hydrogenating lactone and carboxylic acid ester in liquid phase

Process for producing optically active &ggr;-butyrolactone

Provided is a method for the production of 1-menthol, which comprises hydrogenation of piperitenone with a transition metal complex of a specified optically active phosphine to produce pulegone, hydrogenation of the obtained pulegone with a ruthenium-phosphine-amine complex in the presence of base to obtain pulegol, and further hydrogenation of the pulegol with a transition metal catalyst.

Method for producing 1-menthol

Process for the preparation of 4-substituted azetidinone derivatives

A process for producing cyclohexylazetidinone expressed by the formula(IV) comprises condensing the magnesium enolate compound expressed by the formula (II) with acyloxyazetidinone expressed by the formula (III), wherein Me is a methyl group; R.sup.1 is a hydroxyl-protecting group, R.sup.2 is an acyl group, and X is a halogen atom. ##STR1##

Process for producing cyclohexylazetidinone

A process for producing an optically active cyclohexanol derivative represented by formula (I): ##STR1## wherein R.sup.1 represents an alkyl group having 1 to 4 carbon atoms, a hydroxyl group, or a protected hydroxyl group, comprising asymmetrically hydrogenating a cyclohexanone derivative in the presence of a catalyst system composed of a transition metal compound (e.g., transition metal complex), a base (e.g., KOH), and a nitrogen compound (e.g., an amine compound).

Process for preparing optically active cyclohexanol derivatives

To prepare the compound (1'R,3S)-3-(1'-tri-substituted silyloxyethyl)azetidin-2-one, (2S,3R)-2-aminomethyl-3-hydroxybutyric acid is reacted with an alcohol in the presence of at least one compound chosen from the group consisting of thionyl chloride, hydrogen chloride and p-toluene sulfonic acid, thereby obtaining a salt of the corresponding ester. The salt is reacted with a tri-substituted silane in the presence of a metallic catalyst, thereby protecting the hydroxy group of the ester and then reacted with a base, thereby obtaining an ester of (2S,3R)-2-aminomethyl-3-(tri-substituted silyloxy)butyric acid. Subsequently, the ester is transformed into lactam in the presence of a Grignard reagent or a metal amide, thereby obtaining (1'R,3S)-3-(1'-tri-substituted silyloxyethyl)azetidin-2-one. This compound provides a useful base for preparing .beta.-lactam type antimicrobial agents such as carbapenem type agents.

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Kanagawa, Japan

Takaji Matsumoto