21403-95-2

Usage

Uses

Used in Pharmaceutical Development:
1-(3,4-Dihydro-2-naphthyl)pyrrolidine is used as a key intermediate in the synthesis of pharmaceuticals for its potential to contribute to the development of new drugs with unique therapeutic properties. Its chiral nature allows for the exploration of different optical isomers, which may exhibit distinct biological activities.
Used in Agrochemicals:
In the agrochemical industry, 1-(3,4-Dihydro-2-naphthyl)pyrrolidine is used as a building block for the creation of novel agrochemicals, potentially enhancing crop protection and yield through the development of new pesticides or herbicides.
Used in Materials Science:
1-(3,4-Dihydro-2-naphthyl)pyrrolidine is employed as a component in the design and synthesis of new materials with specific properties, such as improved conductivity, stability, or responsiveness, which can be applied in various technological and industrial applications.
Organic Synthesis:
1-(3,4-Dihydro-2-naphthyl)pyrrolidine is used as a reactant in organic synthesis processes, allowing for the formation of a wide range of complex organic molecules, contributing to the advancement of chemical research and the discovery of new chemical entities.

InChI:InChI=1/C14H17N/c1-2-6-13-11-14(8-7-12(13)5-1)15-9-3-4-10-15/h1-2,5-6,11H,3-4,7-10H2

Upstream product

• 123-75-1 pyrrolidine 
• 530-93-8 1,2,3,4-tetrahydronaphthalen-2-one 

Downstream Products

• 4024-14-0 1-methyl-2-tetralone 
• 67395-21-5 5,7,7a,8,9,10-hexahydro-7-methoxycarbonyl-6H-benzopyrrolo<1,2-a>indole-7-acetic acid methyl ester 
• 61034-42-2 1-benzyl-3,4-dihydro-1H-naphthalen-2-one 
• 66209-43-6 1-(4-Nitrobenzyl)-2-tetralon 

Relevant academic research and scientific papers

N-(sulfonamido)alkyl[tetrahydro-1H-benzo[e]indol-2-yl]amines: Potent antagonists of human neuropeptide Y Y5 receptor

[3a,4,5,9b-Tetrahydro-1H-benzo[e]indol-2-yl]amines were prepared via reductive amination and concomitant cyclization of α-cyanomethyl-β-aminotetralins. N-acylation with Ω-sulfonamido-carboxylic acids and subsequent reduction afforded a series of N-(sulfonamido)alkyl[tetrahydro-1H-benzo[e]indol-2-yl]amines, which bound to the human neuropeptide Y Y5 receptor with nanomolar affinity. (C) 2000 Elsevier Science Ltd. All rights reserved.

A de novo Synthesis of Oxindoles from Cyclohexanone-Derived γ-Keto-Ester Acceptors Using a Desaturative Amination-Cyclization Approach

Here we report a desaturative approach for oxindole synthesis. This method uses simple ethyl 2-(2-oxocyclohexyl)acetates and primary amine building blocks as coupling partners. A dual photoredox cobalt manifold is used to generate a secondary aniline that, upon heating, cyclizes with the pendent ester functionality. The process operates under mild conditions and was applied to the modification of several amino acids, the blockbuster drug mexiletine, as well as the formation of dihydroquinolinones.

1 microwave-induced montmorillonite-mediated facile synthesis of enamines

Montmorillonite clay-mediated simple and high yielding protocol for the synthesis of various enamines with secondary amines and ketones is developed under microwave condition. This protocol is very convenient to accesses the enamines from cyclic amines with various carbonyl compounds in high yield under mild reaction conditions with short reaction time.

Bifunctional Br?nsted Base Catalyst Enables Regio-, Diastereo-, and Enantioselective Cα-Alkylation of β-Tetralones and Related Aromatic-Ring-Fused Cycloalkanones

The catalytic asymmetric synthesis of both α-substituted and α,α-disubstituted (quaternary) β-tetralones through direct α-functionalization of the corresponding β-tetralone precursor remains elusive. A designed Br?nsted base-squaramide bifunctional catalyst promotes the conjugate addition of either unsubstituted or α-monosubstituted β-tetralones to nitroalkenes. Under these reaction conditions, not only enolization, and thus functionalization, occurs at the α-carbon atom of the β-tetralone exclusively, but adducts including all-carbon quaternary centers are also formed in highly diastereo- and enantioselective manner.

2-(CYCLIC AMINO)-PYRIMIDONE DERIVATIVES AS TPK1 INHIBITORS

A compound represented by the formula (I), an optically active isomer thereof, or a pharmaceutical acceptable salt thereof (I) wherein R2 represents a hydrogen or the like; R3 represents methyl group or the like; R20 represents a halogen atom or the like; q represents an integer of 0 to 3; Z represent nitrogen atom, CH, or the like; R4 represents hydrogen or the like; R5 represents hydrogen or the like; R6 represents a substituted alkyloxy and the like; p represents an integer of 0 to 3; X represents bond, CH2, oxygen atom, NH, or the like; any one or more of R5 and R6, R5 and R4, R6 and R4, X and R5, X and R4, X and R6, and R6 and R6 may combine to each other to form a ring, which is used for preventive and/or therapeutic treatment of a disease caused by tau protein kinase 1 hyperactivity such as a neurodegenerative diseases (e.g. Alzheimer disease).

The synthesis of novel cis-α-substituted-β-aminotetralins

Teteralones were converted, in 1 to 3 steps, to α-substituted tetralones. Subsequent reductive amination with ammonium acetate/sodium cyanoborohydride gave the corresponding α-substituted-β-aminotetralins, on a multigram scale, with minimal chromatography for the entire transformation.

N-(iodopropenyl)-octahydrobenzo[f]- and -[g]quinolines: Synthesis and adrenergic and dopaminergic activity studies

A series of N-(iodopropenyl)-octahydrobenzo[f]- and -[g]quinolines was synthesized and assayed in vitro for their dopaminergic and α-adrenergic activity. Structure-activity relationship (SAR) analysis revealed that the tested benzoquinolines exhibited activity at the D1 rather than the D2 receptor sites in contrast to the D2 receptor subfamily activity reported for their aminotetralin congeners. N-Iodopropenyl substitution was apparently a decisive factor for D1 activity independent of ring substitution pattern. Considering the structural factors influencing α-adrenergic activity, in a general trend, N-iodopropenyl analogues were α1-active, with the ring- hydroxylated congeners exhibiting the highest affinity. Affinity to the α2 receptor was even higher with no detectable trend of SAR. However, a combination of the linear arrangement of the [g]-ring system, combined with the ring hydroxyl and the N-iodopropenyl substitution in compound 5c, resulted in a significant enhancement of α2 activity in this series as demonstrated by an IC50 value of 0.5 nM. A new synthetic approach to the [g]benzoquinoline system is also described.

Synthesis of Enamines from Cycloalkanones and Secondary Cyclic Amines using K-10 Montmorillonite Clay

The synthesis of enamines from cycloalkanones and secondary cyclic amines has been carried out in 85-95percent yield in the presence of K-10 montmorrilonite clay and with azeotropic removal of the water formed in the condensation.

Enynones in Organic Synthesis. 8. Synthesis of the Antimicrobial-Cytotoxic Agent Juncusol and Members of the Effusol Class of Phenols

Two new syntheses of phenols have been developed which have been utilized in an efficient preparation of the antimicrobial-cytotoxic agent juncusol (22) and several members of the effusol (23) class of phenols.These results complement our earlier studies with enynones of type 42 and provide for the highly efficient conversion of 42 to either methylenecyclopentenones 45 or phenols of type 47 or 54 with virtually 100percent selectivity.

Radical cyclisations of imines and hydrazones

Radical cyclisation of sp3 carbon-centred radicals onto imines and hydrazones provides a new method for the synthesis of 5- and 6-membered ring nitrogen heterocycles. Cyclisation onto the electrophilic carbon of the C=N group and 5-exo stereoelectronic selectivity are the dominating mechanistic parameters. The C-centred radical intermediates were generated from benzeneselenyl precursors using Bu3SnH.