Simple exploration of 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

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Selective Hydrogenation of Carboxylic Acids to Alcohols or Alkanes Employing a Heterogeneous Catalyst

The chemoselective hydrogenation of carboxylic acids to either alcohols or alkanes is reported, employing a heterogeneous bimetallic catalyst consisting of rhenium and palladium supported on graphite. alpha-Chiral carboxylic acids were hydrogenated without loss of optical purity. The catalyst displays a reverse order of reactivity upon hydrogenation of different carboxylic functions with esters being less reactive than amides and carboxylic acids. This allows for chemoselective hydrogenation of an acid in the presence of an ester or an amide function.

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

Simple exploration of 2-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Difunctionalization of the C-N Bond through tert-Butylnitrite-Initiated C-N Cleavage of 1,2,3,4-Tetrahydroisoquinolines and N, N?-Diarylimidazolidines under Transition-Metal-Free Conditions

Difunctionalization of the saturated C-N bond of 1,2,3,4-tetrahydroisoquinolines and N,N?-diarylimidazolidines was achieved using TBN as the metal-free initiator, providing a series N-nitrosoaminoaldehydes in high yields. Mechanistic study shows that the TBN-derived tBuO radical initiated the sp3 C-H bond activation, and the C-N bond cleavage was mediated by an iminium intermediate. This reaction provided a new way to cleave an inert C-N bond under mild and metal-free conditions, realizing the construction of molecular complexity through difunctionalization of the C-N bond.

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

Archives for Chemistry Experiments of 2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

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Explicit Solvation of Carboxylic Acids for Vibrational Circular Dichroism Studies: Limiting the Computational Efforts without Losing Accuracy

On the basis of a comprehensive analysis of experimental and theoretical IR and vibrational circular dichroism (VCD) spectra, we make suggestions for solvation schemes for carboxylic acids. More specifically, we have studied two chiral carboxylic acids in solvents of different polarity and hydrogen bonding capabilities and verify previously proposed solute-solvent structures for their general applicability. Explicit solvation with acetonitrile-d3 is shown to be most important for carboxylic acid groups directly attached to a stereocenter, while dimethylsulfoxide-d6 should always be considered explicitly in spectra analysis. In order to circumvent the need to consider dimerization with calculations on the full homodimer in nonpolar solvents such as chloroform-d1, we quantitatively evaluate the quality of truncated models. Methanol-d4 is concluded to be the most challenging solvent for VCD studies of carboxylic acids, as the acid strength affects the hydrogen bonding strength to methanol and thus significantly determines the degree and effect of solvation. With the help of matrix-isolation IR spectroscopy, we also characterize the monomeric species of alpha-phenylpropionic acid.

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

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Ferritin encapsulation of artificial metalloenzymes: Engineering a tertiary coordination sphere for an artificial transfer hydrogenase

Ferritin, a naturally occuring iron-storage protein, plays an important role in nanoengineering and biomedical applications. Upon iron removal, apoferritin was shown to allow the encapsulation of an artificial transfer hydrogenase (ATHase) based on the streptavidin-biotin technology. The third coordination sphere, provided by ferritin, significantly influences the catalytic activity of an ATHase for the reduction of cyclic imines.

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

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Exogenous proline stimulates type I collagen and HIF-1alpha expression and the process is attenuated by glutamine in human skin fibroblasts

Abundance of proline (Pro) in collagen molecule led us to investigate whether Pro supply affects collagen biosynthesis in human skin fibroblasts. Treatment of the cells with milimolar concentrations (5 and 10?mM) of Pro for 24 and 48?h contributed to increase in alpha1 subunit of collagen type I (COL1A1) expression in both cells and culture medium. However, the effect was more pronounced in glutamine-free medium. In such condition, Pro induced collagen expression by about twofold in the cells, while in the medium only by about 30% during 24?h incubation, compared to control. In the presence of glutamine (Gln), exogenous Pro stimulated intracellular collagen expression only by about 30% during 24?h of fibroblasts incubation, and it was not accompanied by adequate increase of collagen secretion into medium. Gln alone stimulated the processes by about 2?3 fold during the course of the experiment. Pro-dependent increase in collagen expression in Gln-free medium was accompanied by increase in prolidase activity and expression of pAkt. In both Gln-free medium and Gln-supplemented medium, Pro induced expression of p53 and HIF-1alpha. The data suggest that availability of Gln, as a substrate for Pro biosynthesis, determine the utilization of exogenous Pro for the collagen biosynthesis.

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

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Expanding the chemical diversity in artificial imine reductases based on the biotin-streptavidin technology

We report on the optimization of an artificial imine reductase based on the biotin-streptavidin technology. With the aim of rapidly generating chemical diversity, a novel strategy for the formation and evaluation of biotinylated complexes is disclosed. Tethering the biotin-anchor to the Cp* moiety leaves three free coordination sites on a d6 metal for the introduction of chemical diversity by coordination of a variety of ligands. To test the concept, 34 bidentate ligands were screened and a selection of the 6 best was tested in the presence of 21 streptavidin (Sav) isoforms for the asymmetric imine reduction by the resulting three legged piano stool complexes. Enantiopure alpha-amino amides were identified as promising bidentate ligands: up to 63 % ee and 190 turnovers were obtained in the formation of 1-phenyl-1,2,3,4-tetrahydroisoquinoline with [IrCp*biotin(L-ThrNH2)Cl]?SavWT as a catalyst. Biotinspired! A new strategy for the generation of chemical diversity in artificial transfer hydrogenases (ATHases) based on the biotin-streptavidin technology is disclosed. By combining a biotinylated MCp* fragment with 34 commercially available ligands in the presence of wild-type streptavidin, promising candidates for the asymmetric reduction of imines are identified. Selected ligands are screened against 21 streptavidin isoforms and the performance of the resulting constructs is evaluated.

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

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

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Transition-Metal-Free Dehydrosilylative Difluoroamidation of Tetrahydroisoquinolines under Mild Conditions

Disclosed herein is a dehydrosilylative difluoroamidation of alpha-Csp3-H of tetrahydroisoquinolines with alpha,alpha-difluoro-alpha-TMS-acetamides. The process, which occurs at ambient temperature in the absence of any transition metals, provides direct access to a broad range of alpha,alpha-difluoroacetamide-substituted tertiary amine derivatives in high yields. Moreover, the method was successfully applied in the Csp3-H-directed difluorophosphorylation and difluorocarboxylation under the same conditions.

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

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N-phenacylpyridinium bromides as acid corrosion inhibitors

The inhibiting effect of N-phenacylpyridinium bromides with the amide group in the pyridine ring on corrosion of carbon steel in 3 M sulfuric acid is studied. A relationship between the nature of substituents at the amide group and the corrosion-protective properties of the compounds studied is revealed. Compounds demonstrating high protection efficiency in acid solutions at elevated temperatures are found.

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

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Gold-complexes catalyzed oxidative alpha-cyanation of tertiary amines

Oxidative alpha-cyanation of tertiary amines is catalyzed by gold complexes with trimethylsilyl cyanide to afford the corresponding alpha-aminonitriles in the presence of tert-butyl hydroperoxide in good to excellent yields under acid-free conditions at room temperature.

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

A new application about (S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Study on synthesis and biological effects of a series of 3,4-dihydroisoquinoline-2(1H)-carboxamide derivatives

In this paper, we have reported the synthesis and biological evaluation of nineteen (S)-N-substituted-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxamide derivatives as novel candidate antidepressant and anticonvulsant agents. Compounds 2h, 2k, 2r, and 2s exhibited better potent antidepressant activity and displayed the antidepressant effects in a dose-dependent manner from 10 to 30 mg/kg in the FST and TST. And, we found that the best antidepressant effect of compounds 2r and 2s are likely mediated by an increase in central nervous system 5-HT and NE. In addition, compounds 2r and 2s also exhibited the anticonvulsant activity against MES-induced seizures. Thus, compounds 2r and 2s may be a useful antidepressant adjunct therapy for treating depression in patients with epilepsy. In addition, compounds 2r and 2s showed the anti-inflammatory activity and the excellent analgesic activity. Several scholars have postulated the anti-inflammatory and analgesic effects of antidepressant drugs, suggesting that they may be possess a similar mechanism of action.

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