Cyclohexane tricarboxylic acid derivative and method for the pre

Details Cyclohexane tricarboxylic acid derivative and method for the pre Cyclohexane tricarboxylic acid derivative and method for the pre

1996-02-13

1998-03-03

Burn, Brian M.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

562509, C07C 6974

Patent

active

057236500

ABSTRACT:
Disclosed is a novel compound having activity as an ionophore for ion transport, which is a monoester or monoamide of 1,3,5-trimethyl-1,3,5-cyclohexane tricarboxylic acid, i.e. Kemp's triacid or the stereoisomer thereof, the group R in the ester group --COOR or in the amide group --CONHR being an aralkyl group or aryloxyalkyl group having 7 to 20 carbon atoms. The monoester and monoamide derivatives can be synthesized from anhydride of Kemp's triacid by subjecting the anhydride to a ring-opening esterification or amidation reaction with an alcohol or amine. On the other hand, both of the stereoisomers can be obtained by the dehydrohalogenation reaction of 1,3,5-trimethyl-1,3,5-cyclohexane tricarboxylic acid anhydride acid halide with an alcohol or amine followed by the ring-opening hydrolysis reaction on the anhydride group.

REFERENCES:
Curran et al., J. Org. Chem., 1994, vol. 59, pp. 3522-3529.
Ikeura et al., Chemistry Letters, 1990, pp. 169-172.
Menger et al., J. Am. Chem. Soc., 1988, vo. 110, pp. 6794-6796 & Supplemental Material Page.

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