1391440-71-3

Usage

Uses

Used in Pharmaceutical Industry:
(1S,3S)-1,3-DIALLYL-1,2,3,4-TETRAHYDROISOQUINOLINE is used as a precursor for the synthesis of other biologically active compounds due to its unique structure and potential medicinal applications.
Used in Medicinal Chemistry Research:
(1S,3S)-1,3-DIALLYL-1,2,3,4-TETRAHYDROISOQUINOLINE is used as a subject of interest for further research and development in the field of pharmaceuticals, particularly for its potential pharmacological properties, including analgesic and neuroprotective effects.
Used in Drug Addiction Treatment:
(1S,3S)-1,3-DIALLYL-1,2,3,4-TETRAHYDROISOQUINOLINE is used as a potential treatment for drug addiction, as it has been studied for its potential use in this area.
Used in Neuroprotection:
(1S,3S)-1,3-DIALLYL-1,2,3,4-TETRAHYDROISOQUINOLINE is used as a neuroprotective agent, as it has been found to have potential neuroprotective effects.

Upstream product

• 119-65-3 isoquinoline 
• 18925-10-5 allylzinc bromide 
• 688-61-9 Triallylborane 

Relevant academic research and scientific papers

Synthesis of bridged azabicycles from pyridines and pyrrole by a diallylboration - Ring closing metathesis sequence

A straightforward method for the preparation of bridged azabicycles by a diallylboration-ring closing metathesis (RCM) sequence was elaborated. The precursors for the metathesis reaction were prepared by reductive irons-diallylation of aromatic heterocycles such as pyridines, isoquinoline and pyrrole with triallylborane and an alcohol. Heating of the irons isomers with one equivalent of triallylborane allowed the corresponding cis isomers - or (in the case of pyrrole) a mixture of cis and trans isomers - to be obtained. Boc protection of the amine function gave the precursor for the RCM reaction with axial orientations of allylic groups. The chemical yields of this stage are very good and the amounts of Grubbs' catalyst required for the reaction do not exceed 2.5 mol-% (first generation cat.) or 3.7 mol-% (second generation cat.). Azabicyclo[4.2.1]nonene, obtained from pyrrole, is a key structural motif of the toxin pinnamine. The structures of cis-1,3-diallyl-1,2,3,4- tetrahydroisoquinoline and azabicyclo[4.3.1]-decadiene were studied by single-crystal X-ray analysis. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Allylmetallation of benzoazaheterocycles with allylic derivatives of zinc. Synthesis of 1,4-ethano-2,3-dihydroisoquinolines and allylated heterocycles

Allylmetallation of isoquinolines, quinoline, and quinoxaline with allylic derivatives of zinc was examined for the first time. A convenient procedure was discovered and developed for the synthesis of 1,4-ethano-2,3-dihydroisoquinolines based on the reactions of isoquinolines with allylic derivatives of zinc. This multistage process involves double allylmetallation of the heterocyclic ring followed by cyclization through intramolecular carbometallation of the C=C bond. The structures of three key derivatives of 1,4-ethano-2,3-dihydroisoquinoline were established by X-ray diffraction analysis. The reactions of quinoxaline with allyl-and methallylzinc bromide proceeded stereospecifically to form trans-2,3-diallylated 1,2,3,4-tetrahydroquinoxalines. Heating of quinoline with methallylzinc bromide in THF afforded 4-methallylquinoline in nearly quantitative yield. The initially formed 1,4-metallation product underwent aromatization through elimination of HZnBr.

New growth regulators of corn based on N-mono- and N,N-bis-3-butenyldichloroacetamides

Allylboration of imines, nitriles (including hydrocyanic acid), amides, lactams, aromatic azaheterocycles (pyridines, isoquinoline, and pyrrole) was used to synthesize a series of mono- and bis-3-butenylamines with different structures, which were converted to dichloroacetamides, new analogs of a known safener (herbicide antidote) Dichlormid successfully used in the cultivation of corn throughout the world. Biological tests for the germination of corn seeds showed that most of the dichloroacetamides obtained have growth-stimulating activity, which is mainly directed on the development of the root system. Compounds 2f, trans- and cis-2n, cis-2s, and 2t demonstrated outstanding activity, exceeding from two to three times the stimulating effect of Dichlormid on the developing root system of maize seedlings.

Adducts of Triallylborane with Ammonia and Aliphatic Amines as Stoichiometric Allylating Agents for Aminoallylation Reaction of Carbonyl Compounds

Triallylborane-amines adducts are effective stoichiometric allylating agents in the aminoallylation reaction of carbonyl compounds in methanol. Moreover, copper-catalyzed diastereoselective allylation of Ellman's imine was achieved with triallylborane-methylamine adduct.