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

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Partial purification and substrate specificity of flavin-containing monooxygenase from rat brain microsomes

Flavin-containing monooxygenase (FMO) was partially purified from rat brain microsomes through two successive chromatographies on columns of DEAE Sepharose and 2′,5′-ADP Sepharose. The specific activity, benzydamine N- oxidation of partially purified brain FMO, was 122-fold higher than that of microsomes. A single band of 60 kDa was recognized by Western blotting analysis with anti-rat liver FMO. The K(m) value of brain FMO for thiourea was 4-fold lower, but that for cysteamine was 10-fold higher than that of liver FMO. The enzymatic activity for n-octylamine was detected in neither brain nor liver FMO. Kinetic analysis for neurotoxins also revealed that K(m) values of brain FMO for 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), 1,2,3,4-tetrahydroisoquinoline (TIQ) and N-methyl TIQ (NMTIQ) were lower than those of liver FMO. These results indicate that rat brain FMO catalyzes several substrates of liver FMO involving neurotoxins, but it seems likely that the kinetic properties of brain FMO are somewhat different from those of liver FMO.

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

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STEREOCHIMIE DE LA CYCLOADDITION DES DIARYLNITRILIMINES SUR LES N-ALKYL ET LES DIALKYL-1,2 DIHYDRO-1,2 ISOQUINOLEINES

The PMR spectroscopic properties (60 MHz) of cycloadducts of diarylnitrilimins towards 1,2-dihydroisoquinolines mono alkylated at the N-atom or dialkylated at the C1-carbon and N-atoms have been studied.Date allow us to determine the stereochemistry of the cycloaddition reaction which is regio and diastereospecific.Configuration and conformation of the cycloadducts are specified.

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

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Computational spectroscopy of a bichromophoric molecule, 2-methyl-1,2,3,4-tetrahydroisoquinoline, in solutions

An ab initio calculation of the title molecule was performed to interpret previously observed electronic spectra of the title system. Since the computation concerns the isolated molecule, possible effects of solvent molecules had to be taken into account, especially for such as Rydberg states. The S3 ? S0, S2 ? S1 n, and S1n ? S0 absorption bands are (re)assigned to the excited states of the Lb, L a/CT, and nNsigma (3s) states, respectively. The minor S1a ? S0 absorption observed at the red area of the S1n ? S0 band in acetonitrile is reinterpreted as being a nNpi (CT) state. Correspondingly, the pi, nN, and aN fluorescence spectra are (re)ascribed to the excited states of the Lb, nNsigma*, and nNpi states, respectively. The nNsigma* and nN* states are found to be restricted to the equatorial and axial conformers, respectively. The exceptionally long progression of the pi fluorescence in hexane is interpreted as being due to the closeness of the La and Lb states.

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

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

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TiO2 Nanoparticles Functionalized with Non-innocent Ligands Allow Oxidative Photocyanation of Amines with Visible/Near-Infrared Photons

Photosynthesis is an efficient mechanism for converting solar light energy into chemical energy. We report on a strategy for the aerobic photocyanation of tertiary amines with visible and near-infrared (NIR) light. Panchromatic sensitization was achieved by functionalizing TiO2 with a 2-methylisoquinolinium chromophore, which captures essential features of the extended ?-system of 2,7-diazapyrenium (DAP2+) dications or graphitic carbon nitride. Two phenolic hydroxy groups make this ligand highly redox-active and allow for efficient surface binding and enhanced electron transfer to the TiO2 surface. Non-innocent ligands have energetically accessible levels that allow redox reactions to change their charge state. Thus, the conduction band is sufficiently high to allow photochemical reduction of molecular oxygen, even with NIR light. The catalytic performance (up to 90% chemical yield for NIR excitation) of this panchromatic photocatalyst is superior to that of all photocatalysts known thus far, enabling oxidative cyanation reactions to the corresponding alpha-cyanated amines to proceed with high efficiency. The discovery that the surface-binding of redox-active ligands exhibits enhanced light-harvesting in the red and NIR region opens up the way to improve the overall yields in heterogeneous photocatalytic reactions. Thus, this class of functionalized semiconductors provides the basis for the design of new photocatalysts containing non-innocent donor ligands. This should increase the molar extinction coefficient, permitting a reduction of nanoparticle catalyst concentration and an increase of the chemical yields in photocatalytic reactions.

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

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Benzoyl peroxide (BPO)-promoted oxidative trifluoromethylation of tertiary amines with trimethyl(trifluoromethyl)silane

The benzoyl peroxide (BPO)-promoted oxidative functionalization of tertiary amines under transition-metal-free reaction conditions was developed. Various 1-trifluoromethylated tetrahydroisoquinoline derivatives were prepared by employing this method. It constitutes the first example of direct trifluoromethylation of tertiary amines.

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

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L-selectride as a convenient reagent for the selective cleavage of carbamates

L-Selectride(R) was shown to selectively cleave methyl carbamates in the presence of more sterically demanding carbamates, including the selective cleavage of a methyl carbamate in the presence of an N-Boc group.

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

Discovery of 2-Methyl-1,2,3,4-tetrahydroisoquinoline

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Tropylium ion mediated alpha-cyanation of amines

Tropylium ion mediated alpha-cyanation of amines is described. Even in the presence of KCN, tropylium ion is capable of oxidizing various amine substrates, and the resulting iminium ions undergo salt metathesis with cyanide ion to produce aminonitriles. The byproducts of this transformation are simply cycloheptatriene, a volatile hydrocarbon, and water-soluble potassium tetrafluoroborate. Thirteen total substrates are shown for the alpha-cyanation procedure, including a gram scale synthesis of 17beta-cyanosparteine. In addition, a tropylium ion mediated oxidative aza-Cope rearrangement is demonstrated.

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

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The Thermolysis of Heterocyclic Aminimines

Aminimines derived from six heterocyclic tertiary amines were thermolyzed in t-butyl alcohol at ca. 80 deg.N-Methylindoline gave a good yield of the ring-opened product, and a double elimination on 1,4,4-trimethylpiperidine gave 3,3-dimethyl-1,4-pentadiene.The aminimine derived from quinuclidine was stable to elimination under these conditions.Simple elimination products were not obtained from N-methylpyrrolidine, N-methylpiperidine, or N-methyltetrahydroisoquinoline.

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

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Iron-Catalyzed Methylation Using the Borrowing Hydrogen Approach

A general iron-catalyzed methylation has been developed using methanol as a C1 building block. This borrowing hydrogen approach employs a Knoelker-type (cyclopentadienone)iron carbonyl complex as catalyst (2 mol %) and exhibits a broad reaction scope. A variety of ketones, indoles, oxindoles, amines, and sulfonamides undergo mono- or dimethylation in excellent isolated yields (>60 examples, 79% average yield).

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

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

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Asymmetric reduction of cyclic imines catalyzed by a whole-cell biocatalyst containing an (S)-imine reductase

Biocatalytic imine reduction: A whole-cell recombinant E. coli system, producing an (S)-selective imine reductase (IRED) from Streptomyces sp. GF3546, is developed. This biocatalyst is used for the enantioselective reduction of a broad range of substrates such as dihydroisoquinolines and dihydro-beta- carbolines as well as iminium ions. Copyright

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