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Chalcone derivatives and process for producing the same
| Details |
Inventors: Takagaki, Hidetsugu; Nakanishi, Shigenori; Abe, Masayoshi; Ohki, Hiromi; Sano, Yoshiyuki;
Assignee: Dainippon Ink and Chemicals, Inc. (Tokyo, JP)
Primary Examiner: Chan; Nicky
Assistant Examiner:
Attorney, Agent or Firm: Oblon, Spivak, McClelland, Maier & Neustadt
Chalcone derivatives having at least one tetrahydropyranyloxy group is disclosed. Typically, the compounds are represented by general formula (I) ##STR1## wherein X and X' each represent a tetrahydropyranyl group, R and R', which are then same or different, each represent an alkyl group or a hydrogen atom, n and n' each are an integer of from 0 to 5, m and m' each are integers of from 0 to 5, provided that n+n' is 1 or more, and that n+m is an integer of from 0 to 5 and n'+m' is an integer of from 0 to 5. Also, disclosed are processes for producing the chalcone derivatives starting from acetophenone or its derivative and benzaldehyde or its derivative at least one of which has at least one tetrahydropyranyloxy group. Further, disclosed is 2,3,4,2',4'-pentahydroxychalcone. |
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DETAILED DESCRIPTION OF THE INVENTION The novel chalcone derivatives having at least one tetrahydropyranyloxy group which the present invention provides, for example, those compounds in which at least one hydroxyl group in the hydroxychalcone is substituted with a tetrahydropyranyloxy group, include compounds represented by general formula (I) below. ##STR3## wherein X and X' each represent a tetrahydropyranyl group, R and R', which are the same or different, each represent an alkyl group or a hydrogen atom, n and n' each are an integer of from 0 to 5, m and m' each are integers of from 0 to 5, provided that n+n' is 1 or more, and that n+m is an integer of from 0 to 5 and n'+m' is an integer of from 0 to 5. Preferred examples of the chalcone compounds are those in which n, n', m, and m' each are an integer of from 1 to 3, provided that n+m and n'+m' each are an integer of from 1 to 3. In this case, combinations of n and n' being an integer of from 1 to 3 and m and m' each being 0 may also be possible. As specific compounds included in the above-described preferred examples, there can be cited, for example, the following compounds. ##STR4## Also, compounds can be used which have a hydroxyl group at the 2-position of acetophenone skeleton and are represented by general formula (II) below. ##STR5## wherein X and X' each represent a tetrahydropyranyl group, R and R', which are the same or different, each represent an alkyl group or a hydrogen atom, n is an integer of from 0 to 2, n' is an integer of from 0 to 3, m is an integer of from 0 to 2, and m' is an integer of from 0 to 3, provided that n+n' is 1 or more, and that n+m is an integer of from 0 to 3 and n'+m' is an integer of from 1 to 3. Specific compounds embraced by general formula (II) include the following compounds. ##STR6## In the present invention, in order to produce chalcone derivatives having at least one tetrahydropyranyloxy group in the chalcone skeleton, acetophenone having at least one tetrahydropyranyloxy group or its derivative is reacted by Claisen condensation with benzaldehyde or its derivative, or alternatively acetophenone or its derivative is reacted by Claisen condensation with benzaldehyde having at least one tetrahydropyranyloxy group or its derivative
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