1462-93-7

Usage

Uses

Used in Scientific Research:
6-Ethyl-2,3,4,5-tetrahydropyridine is utilized as a neurotoxin in the study of Parkinson's disease. It is employed for [application reason] inducing symptoms akin to those observed in Parkinson's, serving as a valuable tool in understanding the disease's pathophysiology and in the development of potential treatments.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 6-ethyl-2,3,4,5-tetrahydropyridine is used as a key intermediate in the synthesis of other organic compounds. Its specific structural properties make it a versatile building block for the creation of various pharmaceutical agents, contributing to the advancement of medicinal chemistry.
Used in Chemical Synthesis:
6-Ethyl-2,3,4,5-tetrahydropyridine is also used as a chemical intermediate in the synthesis of a range of organic compounds. Its unique structure allows for the development of new chemical entities with potential applications across various fields, including but not limited to pharmaceuticals, materials science, and agrochemicals.

Upstream product

• 1462-92-6 6-methyl-2,3,4,5-tetrahydro-pyridine 
• 74-88-4 methyl iodide 
• 107993-90-8 hepta-5,6-diene-1-amine 
• 10297-06-0 1-chloro-5-hexyne 
• 70396-13-3 chloro-1 heptyne-5 
• 161009-84-3 hepta-4,5-dienylamine 
• 100-39-0 benzyl bromide 
• 1484-80-6 2-ethylpiperidine 
• 85908-96-9 2-oxopiperidine-1-carboxylic acid tert-butyl ester 
• 96333-47-0 2-Piperidin-(2Z)-ylidene-propionic acid ethyl ester 

Downstream Products

• 108201-24-7 2-Ethoxy-9a-ethyl-3,4-diphenyl-7,8,9,9a-tetrahydro-2H,6H-pyrido<2.1-b><1.3>oxazin 
• 108201-17-8 5-Ethyl-2,3-diphenyl-1-azabicyclo<4.3.0>non-2-en-4-on 
• 108201-32-7 6c-Ethyl-1,6b-diphenyl-2-thioxy-1,2,4,5,6,6a,6b,6c-octahydrocyclopropindolizin 
• 27300-27-2 1-(3,4,5,6-tetrahydro-2-pyridyl)-1-ethanone 
• 100-71-0 2-Ethylpyridine 
• 108201-23-6 9a-Ethyl-2-methoxy-3,4-diphenyl-7,8,9,9a-tetrahydro-2H,6H-pyrido<2.1-b><1.3>oxazin 

Relevant academic research and scientific papers

Catalytic intramolecular hydroamination of aminoallenes using titanium and tantalum complexes of sterically encumbered chiral sulfonamides

Catalysis using earth abundant metals is an important goal due to the relative scarcity and expense of precious metal catalysts. It would be even more beneficial to use earth abundant catalysts for the synthesis of common pharmaceutical structural motifs such as pyrrolidine and pyridine. Thus, developing titanium catalysts for asymmetric ring closing hydroamination is a valuable goal. In this work, four sterically encumbered chiral sulfonamides derived from naturally occurring amino acids were prepared. These compounds undergo protonolysis reactions with Ti(NMe2)4 or Ta(NMe2)5 to give monomeric complexes as determined by both DOSY NMR and X-ray crystallography. The resulting complexes are active for the ring closing hydroamination hepta-4,5-dienylamine to give a mixture of tetrahydropyridine and pyrrolidine products. However, the titanium complexes convert 6-methylhepta-4,5-dienylamine exclusively to 2-(2-methylpropenyl)pyrrolidine in higher enantioselectivity than those previously reported, with enantiomeric excesses ranging from 18-24%. The corresponding tantalum complexes were more selective with enantiomeric excesses ranging from 33-39%.

A Commercially Available and User-Friendly Catalyst for Hydroamination Reactions under Technical Conditions

The activity of a simple, commercially available copper salt, [Cu(NCMe)4](BF4) in intramolecular hydroamination reactions of alkynes and allenes is presented. Reactions were successfully carried out in technical acetonitrile in the presence of air. While attempts of alkene hydroamination failed, this catalyst was also found active in intermolecular aza-Michael reactions.

Catalytic intramolecular hydroamination of aminoallenes using titanium complexes of chiral, tridentate, dianionic imine-diol ligands

Alkylation of d- or l-phenylalanine or valine alkyl esters was carried out using methyl or phenyl Grignard reagents. Subsequent condensation with salicylaldehyde, 3,5-di-tert-butylsalicylaldehyde, or 5-fluorosalicylaldehyde formed tridentate, X2/sub

Characterization of three novel enzymes with imine reductase activity

Imine reductases (IRED) are promising catalysts for the synthesis of optically pure secondary cyclic amines. Three novel IREDs from Paenibacillus elgii B69, Streptomyces ipomoeae 91-03 and Pseudomonas putida KT2440 were identified by amino acid or structural similarity search, cloned and recombinantly expressed in E. coli and their substrate scope was investigated. Besides the acceptance of cyclic amines, also acyclic amines could be identified as substrates for all IREDs. For the IRED from P. putida, a crystal structure (PDB-code 3L6D) is available in the database, but the function of the protein was not investigated so far. This enzyme showed the highest apparent E-value of approximately Eapp = 52 for (R)-methylpyrrolidine of the IREDs investigated in this study. Thus, an excellent enantiomeric purity of >99% and 97% conversion was reached in a biocatalytic reaction using resting cells after 24 h. Interestingly, a histidine residue could be confirmed as a catalytic residue by mutagenesis, but the residue is placed one turn aside compared to the formally known position of the catalytic Asp187 of Streptomyces kanamyceticus IRED.

A general method for the synthesis of the most powerful naturally?occurring Maillard flavors

The natural flavors 2-acetyl-1-pyrroline 1a, 2-propionyl-1-pyrroline 1b, 2-acetyl-3,4,5,6-tetrahydropyridine 1c, 2-acetyl-2-thiazoline 1d, 2-propionyl-2-thiazoline 1e, and the artificial flavor 2-acetyl-5,6-dihydro-4H-1,3-thiazine 1f have been prepared by catalytic SeO2 oxidation of the corresponding cyclic imines 6a-c and sulfur cyclic imines 7a-c using TBHP as co-oxidant. The oxidation of the pyrrolines 1a and b is completely regioselective. Professional olfactory evaluation together with the odor threshold of the new flavor 1f is reported.

Regioselective oxyfunctionalization of unactivated tertiary and secondary C-H bonds of alkylamines by methyl(trifluoromethyl)dioxirane in acid medium

Tetrafluoroborate salts of primary, secondary, and tertiary alkylamines are resistant toward N oxidation by methyl(trifluoromethyl)dioxirane (1b), which allows the selective oxidation of aliphatic tertiary and secondary C-H bonds in the alkyl side chain. The oxidations are carried out at 0°C with a ketone-free solution of methyl(trifluoromethyl)-dioxirane (1b) in methylene chloride. By this procedure, within 3 h the tertiary C-H bonds of acyclic, cyclic, and polycyclic amines 2a-e are hydroxylated to give the corresponding amino alcohols 3a-e. In the case of the acyclic amines 2a,b longer reaction times were necessary, and in the strong acid medium the corresponding amino acetamides 4a,b were obtained through Ritter reaction with the solvent acetonitrile. The strong electron-withdrawing nature of the ammonium group deactivates the oxidation of even tertiary C-H bonds at the α and β positions. Secondary C-H bonds of the linear aliphatic primary amines 2f-h were oxidized exclusively at the ∈ position to give the 2,3,4,5-tetrahydro-6-alkylpyridines 6f-h after intramolecular condensation of the corresponding amino ketones 5f-h.

Boric acid: a new regiospecific decarboxylating agent. Syntheses of cyclic imines, β-enaminones, and β-enaminodiketones from β-enaminoesters

The synthesis of cyclic imines 2, β-enaminones 6, and β-enaminodiketones 7 is described.Regio- and stereospecific thermolysis of β-enaminoesters 4 with boric acid permit these preparations in generally good yields. Key words: boric acid, cyclic β-enaminoesters, decarboxylation, cyclic imines, cyclic β-enaminones.

CYCLIC β-ENAMINOESTERS DECARBOXYLATION WITH BORIC ACID : A CONVENIENT SYNTHESIS OF CYCLIC IMINES

Δ1-pyrrolines, Δ1-piperideines and 1-aza 1-cycloheptenes are formed in good yields from the decarboxylation of alkylated cyclic β-enaminoesters with boric acid.