Some scientific research about 2-Methyl-1,2,3,4-tetrahydroisoquinoline

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A unique combined source of “cN” from 1,2-dichloroethane and TMSN3 in the copper-catalyzed cyanation of a C(sp3)-H bond adjacent to a nitrogen atom

A novel combined metal-free “CN” source from trimethylsilyl azide and 1,2-dichloroethane has been developed and successfully applied to copper-catalyzed oxidative cyanation of alpha-C-H tertiary amines for the synthesis of C1-cyanation tetrahydroisoquinoline derivatives with good to excellent yields for the first time.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Awesome and Easy Science Experiments about 118864-75-8

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Enhancing effects of salt formation on catalytic activity and enantioselectivity for asymmetric hydrogenation of isoquinolinium salts by dinuclear halide-bridged iridium complexes bearing chiral diphosphine ligands

Asymmetric hydrogenation of 1- and 3-substituted and 1,3-disubstituted isoquinolinium chlorides using triply halide-bridged dinuclear iridium complexes [{Ir(H)(diphosphine)} 2(mu -Cl)3]Cl has been achieved by the strategy of HCl salt formation of isoquinolines to afford the corresponding chiral 1,2,3,4-tetrahydroisoquinolines (THIQs) in high yields and with excellent enantioselectivities after simple basic workup. The effects of salt formation have been investigated by time-course experiments, which revealed that the generation of isoquinolinium chlorides clearly prevented formation of the catalytically inactive dinuclear trihydride complex, which was readily generated in the catalytic reduction of salt-free isoquinoline substrates. Based on mechanistic investigations, including by 1H and 31P{1H} NMR studies and the isolation and characterization of several intermediates, the function of the chloride anion of the isoquinolinium chlorides has been elucidated, allowing us to propose a new outer-sphere mechanism involving coordination of the chloride anion of the substrates to an iridium dihydride species along with a hydrogen bond between the chloride ligand and the N-H proton of the substrate salt.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Top Picks: new discover of 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline

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NOVEL TETRAHYDROISOQUINOLINE COMPOUNDS FOR USE IN THE DIAGNOSIS AND TREATMENT OF NEURODEGENERATIVE DISEASES

The invention relates to a new class of compounds with high affinity and selectivity towards P-glycoprotein. The invention also relates to the utilization of such compounds in the in vivo diagnosis of neurodegenerative diseases and as medicaments for use in the prevention and treatment of neurodegenerative disease involving P-glycoprotein.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

The Absolute Best Science Experiment for 7-Nitro-1,2,3,4-tetrahydroisoquinoline

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Exploring the active site of phenylethanolamine N-methyltransferase with 1,2,3,4-tetrahydrobenz[h]isoquinoline inhibitors

1,2,3,4-Tetrahydrobenz[h]isoquinoline (THBQ, 11) is a potent, inhibitor of phenylethanolamine N-methyltransferase (PNMT). Docking studies indicated that the enhanced PNMT inhibitory potency of 11 (hPNMT Ki = 0.49 muM) versus 1,2,3,4-tetrahydroisoquinoline (5, hPNMT Ki = 5.8 muM) was likely due to hydrophobic interactions with Val53, Met258, Val272, and Val269 in the PNMT active site. These studies also suggested that the addition of substituents to the 7-position of 11 that are capable of forming hydrogen bonds to the enzyme could lead to compounds (14-18) having enhanced PNMT inhibitory potency. However, these compounds are in fact less potent at PNMT than 11. Furthermore, 7-bromo-THBQ (19, hPNMT Ki = 0.22 mM), which has a lipophilic 7-substituent that cannot hydrogen bond to the enzyme, is twice as potent at PNMT than 11. This once again illustrates the limitations of docking studies for lead optimization.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Can You Really Do Chemisty Experiments About 17680-55-6

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Mn(II)-Catalyzed N -Acylation of Amines

A practical protocol has been developed here for the Mn(II)-catalyzed N -acylation of amines with high yields using N, N -dimethylformamide and other amides as the carbonyl source. The protocol is simple, does not require any acid, base, ligand, or other additives, and encompasses a broad substrate scope for primary, secondary, and heterocyclic amines.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Discovery of 118864-75-8

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Stereoselective Total Syntheses of Solifenacin and N -Acetyl-1-(4-chloro-phenyl)-6,7-dimethoxytetrahydroisoquinoline

A highly stereoselective synthesis of 1-aryl-1,2,3,4-tetrahydroisoquinoline drugs such as solefinacin (muscarinic acetylcholine receptor antagonist) and N-acetyl-1-(4-chlorophenyl)-6,7-dimethoxytetrahydroisoquinoline (AMPA receptor antagonist) has been accomplished using (R)-tert-butanesulfinamide as a chiral source. Chiral tetrahydroisoquinolines have been prepared through the aryl Grignard addition to chiral N-sulfinylimines followed by haloamide cyclization.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

New explortion of 1745-07-9

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Electrochemical Approach for Direct C-H Phosphonylation of Unprotected Secondary Amine

Direct alpha-phosphonylation of an unprotected secondary amine in a single step is of practical importance to amino phophophates. However, this protocol is limited due to the high redox barrier of unprotected amine. In this paper, we report C-H phosphonylation of an unprotected secondary amine via an electrochemical approach in the presence of catalytic carboxylate salt. This metal-free and exogenous oxidant-free method furnishes diverse target molecules with satisfactory yield under mild reaction conditions. Successful application of the protocol in a gram-scale experiment demonstrates the potential utility for further functionalization.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Extracurricular laboratory:new discovery of 2-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Visible-light-induced direct alpha-C(sp3)-H thiocyanation of tertiary amines

Visible-light-induced, eosin Y catalyzed aerobic oxidative alpha-C(sp3)-H thiocyanation of tertiary amines is reported. The reaction proceeds through visible-light-induced in situ generation of the iminium ion followed by attack of -SCN nucleophile. This is the first example of visible-light-initiated formation of C(sp3)-S bond employing organo-photoredox catalysis. Mild reaction conditions and use of air and visible light as the greenest and sustainable reagents at room temperature are the salient features of the protocol.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

More research is needed about 118864-75-8

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Process for preparing polymorphic forms of solifenacin succinate

Polymorphic forms of solifenacin have been prepared and characterized. These polymorphic forms are particularly useful in pharmaceutical compositions.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Extracurricular laboratory:new discovery of 2-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Photoredox catalytic organic reactions promoted with broadband visible light-absorbing Bodipy-iodo-aza-Bodipy triad photocatalyst

The 4-bora-3a,4a-diaza-s-indacene scaffold is known as Bodipy. 2,6-Diiodo-aza-Bodipy (B-1) and the Bodipy-2,6-diiodo-aza-Bodipy triad (B-2) have been used as novel photocatalysts for photoredox catalytic organic reactions with tetrahydroisoquiniline as substrate to prepare highly functionalized organic compounds via a [3 + 2] cycloaddition-aromatization tandem reaction and Cu(i)-catalyzed alkynylation reactions. In distinction to conventional photocatalysts such as Ru(bpy)3Cl2, Eosin Y or Rose Bengal, which are based on a mono-visible light-harvesting chromophore profile and show weak absorption in the visible region, the new photocatalysts are strong visible absorbers (B-1, epsilon = 73000 M-1 cm-1 at 683 nm). More importantly, resonance energy transfer (RET) has been used to increase the absorption of photocatalyst B-2 in the visible region, in which two Bodipy units were used as energy donor and diiodo-aza-Bodipy as energy acceptor. B-2 shows broadband absorption in the range 400-750 nm (epsilon = 165 000 M-1 cm-1 at 504 nm, and 71000 M-1 cm -1 at 683 nm). Iodo-aza-Bodipy is more efficient than conventional photocatalysts such as [Ru(bpy)3]Cl2. Furthermore, the broadband visible light-absorbing B-2 is more efficient as a photocatalyst than previously reported monochromophore photocatalyst B-4 (diiodo-Bodipy). Our results will be useful for the design of efficient organic triplet photosensitizers as photocatalysts for photoredox catalytic organic reactions. This journal is the Partner Organisations 2014.

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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem