10347-88-3

Usage

Uses

Used in Organic Synthesis:
3-TERT-BUTYLADIPIC ACID is used as a reactant for the synthesis of hexamethylenetetrathiafulvalene derivatives with substituted bulky alkyl groups. These derivatives are of significant interest due to their transistor properties, making them valuable in the development of advanced electronic materials and devices.
Used in Chemical Research:
In the field of chemical research, 3-TERT-BUTYLADIPIC ACID is utilized as a building block for the creation of novel compounds with potential applications in various industries. Its unique structure and reactivity make it a promising candidate for the development of new chemical entities with improved properties and functions.
Used in Pharmaceutical Industry:
3-TERT-BUTYLADIPIC ACID may also find applications in the pharmaceutical industry, where it can be used as an intermediate in the synthesis of drug molecules. Its ability to form stable derivatives with specific properties makes it a valuable component in the development of new therapeutic agents.
Overall, 3-TERT-BUTYLADIPIC ACID is a multifaceted chemical compound with a wide range of applications across various industries, including organic synthesis, chemical research, and pharmaceutical development. Its unique properties and reactivity make it an essential component in the creation of innovative materials and products.

Synthesis Reference(s)

Journal of the American Chemical Society, 99, p. 4405, 1977 DOI: 10.1021/ja00455a032Synthesis, p. 915, 1988 DOI: 10.1055/s-1988-27754

Flammability and Explosibility

Notclassified

InChI:InChI=1/C10H18O4/c1-10(2,3)7(6-9(13)14)4-5-8(11)12/h7H,4-6H2,1-3H3,(H,11,12)(H,13,14)/p-2/t7-/m0/s1

Upstream product

• 98-52-2 4-(1,1-dimethylethyl)-cyclohexanol 
• 7360-39-6 1-acetoxy-4-tert-butylcyclohexene 
• 88828-77-7 1,2-Dimethyl-4-tert.-butyl-cyclohex-1-en 
• 60774-46-1 (2R,4S)-4-tert-Butyl-2-phenylsulfanyl-cyclohexanone 
• 98-53-3 4-tercbutyl-cyclohexanone 
• 81842-54-8 4-t-Butyl-2-nitrocyclohexanone 
• 5064-52-8 2-methyl-4-tert-butylcyclohexanone 
• 105661-76-5 (2R,4R)-2,4-dimethyl-9-(1,1-dimethylethyl)-1,5-dioxaspiro<5.5>undecane 
• 106034-33-7 (2R,3R)-8-tert-Butyl-2,3-dimethyl-1,4-dioxa-spiro[4.5]decane 
• 105601-75-0 Acetic acid (1R,3R)-3-((S)-4-tert-butyl-cyclohex-1-enyloxy)-1-methyl-butyl ester 
• 100190-34-9 (S)-4-tert-butyl-1-(trimethylsilyloxy)cyclohexene 
• 80452-16-0 1,2-dimethyl-4-tert-butylcyclohexanol 

Downstream Products

• 5581-94-2 3-tert-Butyl-cyclopentanone 
• 3875-52-3 tert-butylcyclopentane 

Relevant academic research and scientific papers

Efficient oxidation of cycloalkanols by sodium nitrite with molecular oxygen in trifluoroacetic acid

Oxidation of aliphatic cycloalkanols by sodium nitrite in trifluoroacetic acid gave α,ω-dicarboxylic acids in good yields. Adipic acid was obtained in a quantitative yield from cyclohexanol using 1 equiv of sodium nitrite under oxygen atmosphere but the oxidation required more than 3 equiv of sodium nitrite under nitrogen atmosphere. The oxidation method was applicable to the conversion of 1-alkanols to the corresponding carboxylic acids.

Sustainable electroorganic synthesis of lignin-derived dicarboxylic acids

The oxidative ring opening of lignin-derived alkylated cyclohexanols to bio-based alkylated dicarboxylic acids is successfully performed by an electrocatalytic conversion. To establish this transformation as a green method, we developed a simple protocol for the anodic oxidation at nickel oxide-hydroxide (NiOOH) foam anodes in caustic soda in both a batch and flow electrolysis approach.

A new, modulated, oxidative ring cleavage of α-nitrocycloalkanones by Oxone: Synthesis of α,ω-dicarboxylic acids and α,ω-dicarboxylic acid monomethyl esters

By the appropriate choice of the reaction conditions Oxone produces the ring cleavage of α-nitrocycloalkanones affording good yields of α,ω-dicarboxylic acids and α,ω-dicarboxylic acid monomethyl esters, respectively, regardless the ring size and/or the presence of an alkyl group as substituent.

A New Oxidative Cleavage of 2-Nitrocycloalkanones by Hydrogen Peroxide: An Important, Efficient Method for Dicarboxylic Acid or Ketoacid Synthesis

2-Nitrocycloalkanones are smoothly converted into dicarboxylic acids or ketoacids, depending on whether the nitro group is secondary or tertiary, by treatment with aqueous 30percent hydrogen peroxide and potassium carbonate in methyl alcohol solution for 8-10 h at room temperature.

Oxidation of homochiral ketals by rhenium(VII) oxide. V

2-Hydroxyethyl enol ethers react with Re2O7 to produce 2-hydroxyketals. Where homochiral starting enol ethers are employed, greater than 99:1 diastereoselectivities are obtained. The stereocontrol is rationalized by invoking a transition state that approximates the geometry of a metallaoxetane. Finally, homochiral ketals are themselves oxidized to provide 2-hydroxyketals with high diastereoselectivity.

Discovery and Optimization of a Compound Series Active against Trypanosoma cruzi, the Causative Agent of Chagas Disease

Chagas disease is caused by the protozoan parasite Trypanosoma cruzi. It is endemic in South and Central America and recently has been found in other parts of the world, due to migration of chronically infected patients. The current treatment for Chagas disease is not satisfactory, and there is a need for new treatments. In this work, we describe the optimization of a hit compound resulting from the phenotypic screen of a library of compounds against T. cruzi. The compound series was optimized to the level where it had satisfactory pharmacokinetics to allow an efficacy study in a mouse model of Chagas disease. We were able to demonstrate efficacy in this model, although further work is required to improve the potency and selectivity of this series.

TREATMENT OF CHAGAS DISEASE

The invention provides compounds of the formula: wherein L1 and L2 are independently selected from O and S; R1 is C3-C6straight or branched alkyl, C3-C7cycloalkyl, C5-C7cycloalkenyl, adamantly, phenyl or saturated heterocyclyl, any of which being optionally substituted; R2 is H, methyl or ethyl; R5 is NRxCORy, NRxRy, CH2COCH3, CH2C≡N, or a 5- or 6-membered heteroaryl group which is optionally substituted; X, Y and Z are independently N or CH; Rx is independently H or C1-C4alkyl; Ry is independently H, CrC4alkyl, phenyl or benzyl, either of which is optionally substituted; n is 0-3; salts, hydrates and N-oxides, wherein the optional substituents are further defined in the claims. The compounds have utility in the prophylaxis or treatment of trypanosomal diseases, such as T. cruzi (Chagas disease).

PROCESS FOR PRODUCING ALIPHATIC DICARBOXYLIC ACID COMPOUND

The present invention discloses a process for producing an aliphatic dicarboxylic acid compound, which comprises oxidizing, with a nitrite or a nitrate in the presence of trifluoroacetic acid, an alicyclic secondary alcohol compound or an alicyclic ketone compound, in each of which at least one methylene group is bonded to the carbon atom having hydroxyl group bonded thereto or the carbon atom as a member of carbonyl group, wherein the reaction is conducted in the presence of water of 5 mass % or less relative to 100 mass % of the total of the trifluoroacetic acid and the water.

ASYMMETRIC DEPROTONATION OF PROCHIRAL KETONES USING CHIRAL LITHIUM AMIDE BASES

A number of chiral secondary amines have been prepared and used as precursors to the corresponding chiral lithium amide bases.Treatment of either cis-2,6-dimethylcyclohexanone or 4-tert-butylcyclohexanone with a chiral lithium amide, followed by electrophilic quench, gives chiral products in up to 88 percent enantiomeric excess.The results with 4-tert-butylcyclohexanone are in disagreement with an earlier literature report, giving products of lower enantiomeric excess but higher optical rotation.

Chiral products via asymmetric deprotonation of 4-tert-butylcyclohexanone using chiral lithium amide bases

The asymmetric deprotonation of 4-tert-butylcyclohexanone using chiral lithium amide bases gives derived silyl enol ether products in up to 88% ee.