3850-30-4

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-3,3-DIMETHYLBUTANE is used as a pharmaceutical intermediate for the synthesis of various drugs. It plays a crucial role in the production of 1-pyridin-3-yl-3-(1,2,2-trimethyl-propyl)-thiourea, a compound with potential therapeutic applications.
Used in Agrochemical Industry:
2-AMINO-3,3-DIMETHYLBUTANE is also utilized as an intermediate in the synthesis of agrochemicals, contributing to the development of new pesticides and other agricultural products. Its unique chemical structure allows it to be a key component in the creation of effective and targeted agrochemicals.

InChI:InChI=1/C6H15N/c1-5(7)6(2,3)4/h5H,7H2,1-4H3/p+1/t5-/m1/s1

Upstream product

• 75-97-8 3,3-dimethyl-butan-2-one 
• 540-69-2 ammonium formate 
• 10341-64-7 pinacolone oxime 
• 599-02-0 3,3-dimethyl-2-nitrobutane 
• 77287-34-4 formamide 
• 2987-16-8 3,3-dimethylbutyrylaldehyde 
• 23602-17-7 N-(1-phenylethyl)acetamide 
• 107-21-1 ethylene glycol 
• 75-83-2 2,2-Dimethylbutane 
• 141294-38-4 (S,S)-N-(1,2,2-trimethylpropyl)phenylethyl-1-amine α-methylbenzylamine 
• 141393-93-3 (S)-α-methyl-N-(1,2,2-trimethylpropylidene)benzenemethanamine 
• 141294-37-3 (R,R)-N-(1,2,2-trimethylpropyl)phenylethyl-1-amine α-methylbenzylamine 
• 141393-92-2 (R)-α-methyl-N-(1,2,2-trimethylpropylidene)benzenemethanamine 
• 618-36-0 rac-methylbenzylamine 

Downstream Products

• 3907-04-8 Pinakolylamin-phthalsaeuremonoamid 
• 40318-41-0 (3,4-Dimethyl-2,6-dinitro-phenyl)-(1,2,2-trimethyl-propyl)-amine 
• 67329-97-9 1-(2,6-Di-sec-butyl-phenyl)-3-(1,2,2-trimethyl-propyl)-thiourea 
• 67330-74-9 1-(2,6-Diethyl-phenyl)-3-(1,2,2-trimethyl-propyl)-thiourea 
• 67330-83-0 1-(2,6-Diethyl-3-methyl-phenyl)-3-(1,2,2-trimethyl-propyl)-thiourea 
• 67331-00-4 1-(2-Ethyl-6-isopropyl-phenyl)-3-(1,2,2-trimethyl-propyl)-thiourea 
• 67330-78-3 1-(2,6-Diethyl-4-methyl-phenyl)-3-(1,2,2-trimethyl-propyl)-thiourea 
• 67330-94-3 1-(2,6-Diethyl-3,5-dimethyl-phenyl)-3-(1,2,2-trimethyl-propyl)-thiourea 
• 67331-09-3 1-(2,6-Diisopropyl-phenyl)-3-(1,2,2-trimethyl-propyl)-thiourea 
• 67331-16-2 1-(2,6-Diisopropyl-4-methyl-phenyl)-3-(1,2,2-trimethyl-propyl)-thiourea 
• 67331-24-2 1-(2,4,6-Triisopropyl-phenyl)-3-(1,2,2-trimethyl-propyl)-thiourea 
• 71416-28-9 Cyclohex-1-ene-1,2-dicarboxylic acid 1-[(4-chloro-2-fluoro-phenyl)-amide] 2-[(1,2,2-trimethyl-propyl)-amide] 
• 6045-02-9 {(CH₃)3C(CH₃)CHNHBCl}2NCH(CH₃)C(CH₃)3 
• 3850-30-4 (S)-1,2,2-trimethylpropylamine 

Relevant academic research and scientific papers

3- and 4-Substituted 4H-pyrido[4,3-e]-1,2,4-thiadiazine 1,1-dioxides as potassium channel openers: Synthesis, pharmacological evaluation, and structure-activity relationships

4-N-Subsituted and -unsubstituted 3-alkyl- and 3-(alkylamino)-4H- pyrido[4,3-e]-1,2,4-thiadiazine 1,1-dioxides were synthesized and tested vs diazoxide and selected 3-alkyl- and 3-(alkylamino)-7-chloro-4H-1,2,4- benzothiadiazine 1,1-dioxides as potassium channel openers on pancreatic and vascular tissues. Several 4-N-unsubstituted 3-(alkylamino)pyridothiadiazines and some 3-(alkylamino)-7-chlorobenzothiadiazines were found to be more potent than diazoxide for the inhibition of the insulin-releasing process. Moreover, the 3-(alkylamino)pyridothiadiazines appeared to be more selective for the pancreatic than for the vascular tissue. By means of the pharmacological results obtained on pancreatic B-cells, structure-activity relationships were deduced and a pharmacophoric model for the interaction of these drugs with their receptor site associated to the pancreatic K(ATP) channel was proposed. According to their selectivity for the B-cell (endocrine tissue) vs the vascular (smooth muscle tissue) ionic channel, selected 3-(alkylamino)-4H-pyrido[4,3-e]-1,2,4-thiadiazine 1,1-dioxides may serve as pharmacological tools in studying the K(ATP) channels ('pancreatic- like' K(ATP) channels) in other tissues.

Separate Sets of Mutations Enhance Activity and Substrate Scope of Amine Dehydrogenase

Mutations were introduced into the leucine amine dehydrogenase (L-AmDH) derived from G. stearothermophilus leucine dehydrogenase (LeuDH) with the goals of increased activity and expanded substrate acceptance. A triple variant (L-AmDH-TV) including D32A, F101S, and C290V showed an average of 2.5-fold higher activity toward aliphatic ketones and an 8.0 °C increase in melting temperature. L-AmDH-TV did not show significant changes in relative activity for different substrates. In contrast, L39A, L39G, A112G, and T133G in varied combinations added to L-AmDH-TV changed the shape of the substrate binding pocket. L-AmDH-TV was not active on ketones larger than 2-hexanone. L39A and L39G enabled activity for straight-chain ketones as large as 2-decanone and in combination with A112G enabled activity toward longer branched ketones including 5-methyl-2-octanone.

An Ammonium-Formate-Driven Trienzymatic Cascade for ω-Transaminase-Catalyzed (R)-Selective Amination

(R)-Amination mediated by (R)-specific ω-transaminases generally requires costly d-alanine in excess to obtain the desired chiral amines in high yield. Herein, a one-pot, trienzymatic cascade comprising an (R)-specific ω-transaminase, an amine dehydrogenase, and a formate dehydrogenase was developed for the economical and eco-friendly synthesis of (R)-chiral amines. Using inexpensive ammonium formate as the sole sacrificial agent, the established cascade system enabled efficient ω-transaminase-mediated (R)-amination of various ketones, with high conversions and excellent ee (>99%); water and CO2 were the only waste products.

(R)- SELECTIVE AMINATION

The present invention relates to a method for the enzymatic synthesis of enantiomerically enriched (R)-amines of general formula [1][c] from the corresponding ketones of the general formula [1][a] by using novel transaminases. These novel transaminases are selected from two different groups: either from a group of some 20 proteins with sequences as specified herein, or from a group of proteins having transaminase activity and isolated from a microorganism selected from the group of organisms consisting of Rahnella aquatilis, Ochrobactrum anthropi, Ochrobactrum tritici, Sinorhizobium morelense, Curtobacterium pusiffium, Paecilomyces lilacinus, Microbacterium ginsengisoli, Microbacterium trichothecenolyticum, Pseudomonas citronellolis, Yersinia kristensenii, Achromobacter spanius, Achromobacter insolitus, Mycobacterium fortuitum, Mycobacterium frederiksbergense, Mycobacterium sacrum, Mycobacterium fluoranthenivorans, Burkhoideria sp., Burkhoideria tropica, Cosmospora episphaeria, and Fusarium oxysporum.

Asymmetric Amination of Secondary Alcohols by using a Redox-Neutral Two-Enzyme Cascade

Multienzyme cascade approaches for the synthesis of optically pure molecules from simple achiral compounds are desired. Herein, a cofactor self-sufficient cascade protocol for the asymmetric amination of racemic secondary alcohols to the corresponding chiral amines was successfully constructed by employing an alcohol dehydrogenase and a newly developed amine dehydrogenase. The compatibility and the identical cofactor dependence of the two enzymes led to an ingenious in situ cofactor recycling system in the one-pot synthesis. The artificial redox-neutral cascade process allowed the transformation of racemic secondary alcohols into enantiopure amines with considerable conversions (up to 94 %) and >99 % enantiomeric excess at the expense of only ammonia; this method thus represents a concise and efficient route for the asymmetric synthesis of chiral amines. If you know what amine: A redox-neutral two-enzyme cascade encompassing an alcohol dehydrogenase (ADH) and an amine dehydrogenase (AmDH) is constructed for the synthesis of chiral amines from the corresponding racemic alcohols in one pot to afford considerable conversions (up to 94 %) and high enantiomeric excess values (>99 %) at the expense of only ammonia.

A novel chimeric amine dehydrogenase shows altered substrate specificity compared to its parent enzymes

We created a novel chimeric amine dehydrogenase (AmDH) via domain shuffling of two parent AmDHs ('L- and F-AmDH'), which in turn had been generated from leucine and phenylalanine DH, respectively. Unlike the parent proteins, the chimeric AmDH ('cFL-AmDH') catalyzes the amination of acetophenone to (R)-methylbenzylamine and adamantylmethylketone to adamantylethylamine.

Microwave-Enhanced Asymmetric Transfer Hydrogenation of N-(tert-Butylsulfinyl)imines

Microwave irradiation has considerably enhanced the efficiency of the asymmetric transfer hydrogenation of N-(tert-butylsulfinyl)imines in isopropyl alcohol catalyzed by a ruthenium complex bearing the achiral ligand 2-amino-2-methylpropan-1-ol. In addition to shortening reaction times for the transfer hydrogenation processes to only 30 min, the amounts of ruthenium catalyst and isopropyl alcohol can be considerably reduced in comparison with our previous procedure assisted by conventional heating, which diminishes the environmental impact of this new protocol. This methodology can be applied to aromatic, heteroaromatic and aliphatic N-(tert-butylsulfinyl)ketimines, leading, after desulfinylation, to the expected primary amines in excellent yields and with enantiomeric excesses of up to 96 %. Microwave irradiation promotes the asymmetric transfer hydrogenation of N-(tert-butylsulfinyl)imines in 2-propanol catalysed by a ruthenium complex bearing an achiral β-amino alcohol as ligand. After desulfinylation, α-branched primary amines containing aromatic, heteroaromatic and aliphatic substituents are obtained in excellent yields and with enantiomeric excesses of up to 96 %.

Optically active amines by enzyme-catalyzed kinetic resolution

Chiral amines are resolved by an enzyme-catalyzed kinetic resolution. Key steps are the selective acylation of one enantiomer with isopropyl methoxyacetate, separation of the resulting amide from the unreacted antipode, and finally amide hydrolysis. The p

Low-temperature deacylation of N-monosubstituted amides

(Chemical Equation Presented) The (PhO)3P-Cl2 reagent, prepared in situ by titrating a solution of triphenyl phosphite with chlorine, is used to convert N-monosubstituted amides into their corresponding amines. The reaction, if compared to other traditional methods, shows the advantage of very mild conditions and low temperature (-30°C→rt).

Method of inhibiting or treating chemotherapy-induced hair loss

A method for inhibiting hair loss and/or promoting hair growth in chemotherapy and/or radiation therapy patients wherein the (R)-enantiomer of 4-[[(cyanoimino)-[(1,2,2-trimethylpropyl)amino]methyl]amino]benzonitrile is administered prior to, simultaneous with and/or after chemotherapy and/or radiation treatment.