1,3-cyclohexanedione derivatives and 1,3-cyclopentanedione derivatives as buffering molecules in non-aqueous solutions

Patent metadata

Field	Value
Publication number	US-12448345-B2
Application number	US-202017769124-A
Country	US
Kind code	B2
Filing date	Oct 15, 2020
Priority date	Oct 16, 2019
Publication date	Oct 21, 2025
Grant date	Oct 21, 2025

Abstract

This invention relates to 1,3-cyclohexanedione derivatives and 1,3-cyclopentanedione derivatives that have buffering function in non-aqueous solutions and to the use thereof for tuning the conditions to control chemical events in non-aqueous solutions. One aspect of the invention is a method for buffering a non-aqueous solution, including adding a buffering molecule to the non-aqueous solution, in which the non-aqueous solution contains an organic solvent, the buffering molecule is a 1,3-cyclohexanedione derivative or a 1,3-cyclopentanedione derivative, and the buffering molecule is optionally conjugated to a solid support.

First claim

The invention claimed is:

1. In a method of buffering a non-aqueous solution comprising an organic solvent comprising adding a buffering molecule, the improvement wherein said buffering molecule is a compound presented by Formula I:

wherein R 1 to R 5 each are hydrogen oralkyl, cycloalkyl, aryl, heterocycloalkyl, heteroaryl, or acyl, which is optionally substituted with one or more substituents selected from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, nitro, cyano, halogen, hydroxy, acyl, carboxyl, carboxyamide, carboxylic acid ester, haloalkyl, halo-alkoxy, aryl, heterocycloalkyl, and heteroaryl, or Formula II:

wherein R 1 to R 3 each are hydrogen or alkyl, cycloalkyl, aryl, heterocycloalkyl, heteroaryl, or acyl, which is optionally substituted with one or more substituents selected from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, nitro, cyano, halogen, hydroxy, acyl, carboxyl, carboxyamide, carboxylic acid ester, haloalkyl, halo-alkoxy, aryl, heterocycloalkyl, and heteroaryl.

2. A method for controlling structural change of a compound in a non-aqueous solution, wherein an acid or a base is capable of causing structural change of the compound, and
the method comprises preparing a non-aqueous solution comprising the compound and a buffering molecule represented by Formula I:

wherein R 1 to R 5 each are hydrogen alkyl, cycloalkyl, aryl, heterocycloalkyl, heteroaryl, or acyl, which is optionally substituted with one or more substituents selected from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, nitro, cyano, halogen, hydroxy, acyl, carboxyl, carboxyamide, carboxylic acid ester, haloalkyl, halo-alkoxy, aryl, heterocycloalkyl, and heteroaryl, or Formula II:

wherein R 1 to R 3 each are hydrogen or alkyl, cycloalkyl, aryl, heterocycloalkyl, heteroaryl, or acyl, which is optionally substituted with one or more substituents selected from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, nitro, cyano, halogen, hydroxy, acyl, carboxyl, carboxyamide, carboxylic acid ester, haloalkyl, halo-alkoxy, aryl, heterocycloalkyl, and heteroaryl.

3. The method according to claim 2 , wherein the method is for suppressing the structural change of the compound in the non-aqueous solution.

4. The method according to claim 3 , wherein an acid or a base is capable of causing isomerization of the compound, and the method is for suppressing the isomerization of the compound in the non-aqueous solution.

5. The method according to claim 3 , wherein an acid or a base is capable of causing decomposition of the compound, and the method is for suppressing the decomposition of the compound in the non-aqueous solution.

6. The method according to claim 2 , wherein the structural change is for converting the compound to a product having another structure.

7. The method according to claim 6 , wherein the product is produced by reacting two or more molecules of the compound with each other.

8. A non-aqueous solution comprising:
a compound in which an acid or a base is capable of causing structural change of the compound, and
a buffering molecule represented by Formula I:

wherein R 1 to R 5 each are hydrogen or alkyl, cycloalkyl, aryl, heterocycloalkyl, heteroaryl, or acyl, which is optionally substituted with one or more substituents selected from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, nitro, cyano, halogen, hydroxy, acyl, carboxyl, carboxyamide, carboxylic acid ester, haloalkyl, halo-alkoxy, aryl, heterocycloalkyl, and heteroaryl, or Formula II:

wherein R 1 to R 3 each are hydrogen or alkyl, cycloalkyl, aryl, heterocycloalkyl, heteroaryl, or acyl, which is optionally substituted with one or more substituents selected from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, nitro, cyano, halogen, hydroxy, acyl, carboxyl, carboxyamide, carboxylic acid ester, haloalkyl, halo-alkoxy, aryl, heterocycloalkyl, and heteroaryl.

9. An article comprising:
a solid support, wherein the solid support is a resin; and
a buffering molecule conjugated to the solid support and represented by Formula I:

wherein R 1 to R 5 each are hydrogen or alkyl, cycloalkyl, aryl, heterocycloalkyl, heteroaryl, or acyl, which is optionally substituted with one or more substituents selected from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, nitro, cyano, halogen, hydroxy, acyl, carboxyl, carboxyamide, carboxylic acid ester, haloalkyl, halo-alkoxy, aryl, heterocycloalkyl, and heteroaryl, and one of R 1 to R 5 is conjugated to the solid support, or Formula II:

wherein R 1 to R 3 each are hydrogen or alkyl, cycloalkyl, aryl, heterocycloalkyl, heteroaryl, or acyl, which is optionally substituted with one or more substituents selected from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, nitro, cyano, halogen, hydroxy, acyl, carboxyl, carboxyamide, carboxylic acid ester, haloalkyl, halo-alkoxy,
aryl, heterocycloalkyl, and heteroaryl, and one of R 1 to R 3 is conjugated to the solid support.

10. The method according to claim 1 , wherein the compound represented by Formula I is conjugated to a solid support and the compound represented by Formula II is conjugated to a solid support, wherein said solid support is a resin.

Assignees

• Okinawa Inst Science & Tech School Corp

Inventors

• Tanaka Fujie
• Sohail Muhammad

Classifications

• C09K15/06 Primary

  containing oxygen · CPC title

• C07C49/603

  of a six-membered ring, e.g. quinone methides · CPC title

• C07C49/613

  polycyclic · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• C07D209/34

  in position 2 · CPC title