Adamantane derivatives and process for producing them

a technology of adamantane and derivatives, which is applied in the direction of organic compounds/hydrides/coordination complexes, organic chemistry, physical/chemical process catalysts, etc., can solve the problems of difficult introduction of hydroxyl groups (specifically, a plurality of hydroxyl groups) to adamantane by using these processes

Inactive Publication Date: 2007-07-24
DAICEL CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such excellent characteristics cannot be achieved by using conventional polymers.
However, introduction of a hydroxyl group (specifically, a plurality of hydroxyl groups) to adamantane by using these processes is difficult.

Method used

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  • Adamantane derivatives and process for producing them
  • Adamantane derivatives and process for producing them
  • Adamantane derivatives and process for producing them

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0227]Mixture of 10 mmole 1-acetylaminoadamantane (Aldrich chemical Company, Inc.), 1 mmole of N-hydroxyphthalimide (NHPI), 0.05 mmole of vanadium (III) acetylacetonato (V(AA)3) and 25 mL of acetic acid was stirred under an oxygen atmosphere and the conditions represented in Table 1 (temperature and time). The products in the reaction mixture were analyzed by gas chromatography, and, as a result, 1-acetylamino-3-adamantanol (compound 1), 1-acetylamino-3,5-adamantanediol (compound 2) and 1-acetylamino-4-adamantanone (compound 3) were obtained with conversions and yields represented in Table 1.

[0228]

TABLE 1TemperatureTimeConversionYield (%)(° C.)(hr)(%)Comp.1Comp.2Comp.3756896416860209266194Comp.1 (compound 1): 1-acetylamino-3-adamantanol Comp.2 (compound 2): 1-acetylamino-3,5-adamantanediol Comp.3 (compound 3): 1-acetylamino-4-adamantanone

example 2

[0229]A reactor was charged with 10 mmole of adamantane, 1 mmole of NHPI, 0.005 mmole of Co(AA)2 and 25 mL of acetic acid, then equipped with a gas bag of mixed gas (a mixed gas of 2 L of carbon monoxide and 0.5 L of oxygen). The resultant mixture was stirred for 6 hours at a temperature of 60° C. to give 1-carboxyadamantane and 1,3-dicarboxyadamantane.

[0230]A mixture of 10 mmole of 1-carboxyadamantane, 1 mmole of NHPI, 0.05 mmole of V(AA)3 and 25 mL of acetic acid was stirred under an oxygen atmosphere and the conditions represented in Table 2 (time and temperature). As a result, 1-carboxy-3-adamantanol (compound 1), 1-carboxy-3,5-adamantanediol (compound 2) and 1-carboxy-4-adamantanone (compound 3) were obtained with conversions and yields represented in Table 2.

[0231]

TABLE 2TemperatureTimeConversionYield (%)(° C.)(hr)(%)Comp.1Comp.2Comp.3751644483752785912475590641947589452295Comp.1 (compound 1): 1-carboxy-3-adamantanol Comp.2 (compound 2): 1-carboxy-3,5-adamantanediol Comp.3 (co...

example 3

[0232]In the presence of an acid catalyst (p-toluenesulfonic acid), 1-carboxyadamantane obtained in Example 2 was allowed to react with an excess amount of ethanol to give 1-ethoxycarbonyladamantane.

[0233]A mixture of 10 mmole of the 1-ethoxycarboxyadamantane, 1 mmole of NHPI, 0.05 mmole of V(AA)3 and 25 mL of acetic acid was stirred under an oxygen atmosphere and the conditions represented in Table 3 (temperature and time). As a result, 1-ethoxycarbonyl-3-adamantanol (compound 1), 1-ethoxycarbonyl-3,5-adamatanediol (compound 2) and 1-ethoxy-4-carbonyladamantanone (compound 3) were obtained with conversions and yields represented in Table 3.

[0234]

TABLE 3TemperatureTimeConversionYield (%)(° C.)(hr)(%)Comp.1Comp.2Comp.375695581687538668676066348646020925416775159927435Comp.1 (compound 1): 1-ethoxycarbonyl-3-adamantanol Comp.2 (compound 2): 1-ethoxycarbonyl-3,5-adamantanediol Comp.3 (compound 3): 1-ethoxycarbonyl-4-adamantanone

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Abstract

In the presence of an imide compound (e.g., N-hydroxyphthalimide) shown by the formula (2): wherein R1 and R2 independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a cycloalkyl group; or R1 and R2 may bond together to form a double bond or an aromatic or non-aromatic ring; Y is O or OH and n=1 to 3;or the imide compound and a co-catalyst (e.g., a transition metal compound), an adamantane derivative having a functional group such as a nitro group, an amino group, a hydroxyl group, a carboxyl group, a hydroxymethyl group and an isocyanato group is oxidized with oxygen. According to the above method, an adamantane derivative having a hydroxyl group together with a functional group such as a nitro group, an amino group, a hydroxyl group, a carboxyl group, a hydroxymethyl group and an isocyanato group is efficiently obtained.

Description

[0001]This application is the national phase under 35 U.S.C. §371 or prior PCT International Application No. PCT / JP98 / 00904 which has an International filing date of Mar. 5, 1998 which designated the United States of America, the entire contents of which are hereby incorporated by reference.TECHNICAL FIELD[0002]This invention relates to a novel adamantane derivative, which has a hydroxyl group together with a nitro group, an amino group, an acyloxy group, a carboxyl group, a hydroxymethyl group or the like, and to a process for producing the same.BACKGROUND ART[0003]The adamantane has a three-dimensionally symmetric structure and skeletons which insure mutual stabilization of each ring, and, as a result, endowed with distinctive functions. Various copolymers each having enhanced or improved functions or characteristics can be obtained by introducing a hydroxyl group into an adamantane and, if necessary, inducing them into an acrylic acid derivative or a carbonate. There have been pr...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C07C35/22C07C211/00C07C61/12C07D207/40C07D207/444B01J31/00C07C69/757C07C29/50C07C35/37C07C62/06C07C62/24C07C69/00C07C69/96C07C205/18C07C205/41C07C205/55C07C219/24C07C233/23C07C233/32C07C233/74C07C235/40C07C265/10C07C271/34
CPCC07C29/50C07C35/37C07C62/06C07C62/24C07C67/05C07C67/08C07C67/29C07C67/31C07C68/02C07C69/757C07C69/96C07C205/18C07C205/41C07C205/55C07C219/24C07C233/23C07C233/32C07C233/74C07C235/40C07C265/10C07C271/34C07C2603/74C07C69/753C07C69/157
Inventor ISHII, YASUTAKANAKANO, TATSUYAHIRAI, NARUHISA
Owner DAICEL CHEM IND LTD
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