35488-00-7

Usage

Molecular structure

A heterocyclic compound consisting of a six-membered pyridine ring with a double bond between two carbon atoms, and a methyl group attached to the first carbon.

Neurotoxic effects

Selectively destroys dopamine-producing neurons in the substantia nigra region of the brain, leading to symptoms similar to Parkinson's disease.

Research use

Often used to create animal models of Parkinson's disease and to study the mechanisms of dopaminergic neuron degeneration.

Human exposure

Linked to cases of parkinsonism in individuals who have been exposed to illicitly produced MPTP derivatives.

Regulation

MPTP and its derivatives are tightly controlled substances that require special handling and permits for use in research and pharmaceutical applications.

Upstream product

• 695-19-2 N-methyl-4-pyridone 
• 1445-73-4 1-Methyl-4-piperidone 
• 28286-05-7 8-Methyl-1,4-dioxa-8-azoniaspiro<4.5>decan 
• 57330-84-4 ethyl 3,4-dihydro-4-oxo-1(2H)-pyridinecarboxylate 
• 74-88-4 methyl iodide 
• 116414-57-4 4-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-1,2,3,6-tetrahydro-pyridine 
• 27248-04-0 4-((trimethylsilyl)oxy)pyridine 
• 73390-09-7 4,4-Dihydroxy-1-methylpiperidinium-chlorid 
• 116414-58-5 4-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-3,6-dihydro-2H-pyridine 1-oxide 

Downstream Products

• 1572373-72-8 6-(4-methoxyphenyl)-1-methyl-2,3-dihydropyridin-4(1H)-one 
• 116414-59-6 Acetic acid 6-(4-methoxy-benzyl)-1-methyl-1,2,3,6-tetrahydro-pyridin-4-yl ester 
• 116440-58-5 Acetic acid 1-methyl-6-phenylethynyl-1,2,3,6-tetrahydro-pyridin-4-yl ester 
• 116414-61-0 2-(4-Methoxy-benzyl)-1,4-dimethyl-piperidin-4-ol 
• 46826-37-3 2-(4-methoxy-benzyl)-1-methyl-piperidin-4-one 

Relevant academic research and scientific papers

A Visible-Light Promoted Amine Oxidation Catalyzed by a Cp*Ir Complex

Through a rapid screening of Cp*Ir complexes based on a turn-on type fluorescence readout, a [Cp*Ir(dipyrido[3,2-a : 2’,3’-c]phenazine)Cl]+ complex was found to catalyze the blue-light promoted dehydrogenation of N-heterocycles under physiological conditions. In the dehydrogenation of tetrahydroisoquinolines, the catalyst preferentially yielded the monodehydrogenated product, accompanying H2O2 generation. We surmise that this mechanism may be reminiscent of flavin-dependent oxidases.

CeO2-Supported Pd(II)-on-Au Nanoparticle Catalyst for Aerobic Selective α,β-Desaturation of Carbonyl Compounds Applicable to Cyclohexanones

Direct selective desaturation of carbonyl compounds to synthesize α,β-unsaturated carbonyl compounds represents an environmentally benign alternative to classical stepwise procedures. In this study, we designed an ideal CeO2-supported Pd(II)-on-Au nanoparticle catalyst (Pd/Au/CeO2) and successfully achieved heterogeneously catalyzed selective desaturation of cyclohexanones to cyclohexenones using O2 in air as the oxidant. Besides cyclohexenones, various bioactive enones can also be synthesized from the corresponding saturated ketones under open air conditions in the presence of Pd/Au/CeO2. Preliminary mechanistic studies revealed that α-C-H bond cleavage in the substrates is the turnover-limiting step of this desaturation reaction.

Gold nanoparticles on OMS-2 for heterogeneously catalyzed aerobic oxidative α,β-dehydrogenation of β-heteroatom-substituted ketones

In the presence of Au nanoparticles supported on manganese oxide OMS-2 (Au/OMS-2), various kinds of β-heteroatom-substituted α,β-unsaturated ketones (heteroatom = N, O, S) can be synthesized through α,β-dehydrogenation of the corresponding saturated ketones using O2 (in air) as the oxidant. The catalysis of Au/OMS-2 is truly heterogeneous, and the catalyst can be reused.

Hydroxy chalcogenide-promoted Morita-Baylis-Hillman Alkylation reaction: Intermolecular applications with alkyl halides as electrophiles

Hydroxysulfides acted as catalysts to promote the Morita-Baylis-Hillman alkylation reaction of cyclohexenones and dihydropyridinones. The procedure worked efficiently with a variety of halides as electrophiles. Side reactions were in competition with the MBH alkylation, but fine-tuning the reaction conditions minimized their occurence.

Hydroxy Chalcogenide-Promoted Morita-Baylis-Hillman Alkylation Reaction: Intermolecular Applications with Alkyl Halides as Electrophiles

Hydroxysulfides acted as catalysts to promote the Morita-Baylis-Hillman alkylation reaction of cyclohexenones and dihydropyridinones. The procedure worked efficiently with a variety of halides as electrophiles. Side reactions were in competition with the

Gold-catalyzed heterogeneous aerobic dehydrogenative amination of α,β-unsaturated aldehydes to enaminals

Although enaminals (β-enaminals) are very important compounds and have been utilized as useful synthons for various important compounds, they have been synthesized through non-green and/or limited procedures until now. Herein, we have successfully develop

Synthesis of cyclic enones via direct palladium-catalyzed aerobic dehydrogenation of ketones

α,β-Unsaturated carbonyl compounds are versatile intermediates in the synthesis of pharmaceuticals and biologically active compounds. Here, we report the discovery and application of Pd(DMSO)2(TFA)2 as a catalyst for direct dehydrogenation of cyclohexanones and other cyclic ketones to the corresponding enones, using O2 as the oxidant. The substrate scope includes heterocyclic ketones and several natural-product precursors.

Modulation of the reactivity profile of IBX by ligand complexation: Ambient temperature dehydrogenation of aldehydes and ketones to α,β-unsaturated carbonyl compounds

The reactivity profile of IBX can be altered by complexation with various ligands (e. g. 1-4). A new complex, IBX·MPO, is a remarkably effective oxidant and allows the room-temperature dehydrogenation of carbonyl compounds, for example, the formation of cyclooctenones 6 and 7 from cyclooctanone 5. IBX = iodoxybenzoic acid; MPO = 4-methoxypyridine-N-oxide.

1,3-Dioxolanes of N-Substituted 4-Piperidones as Substrates for Dehydrogenations

The applicability of ketals was examined for masking the carbonyl group in N-tertiary 4-piperidones during the dehydrogenation using mercury-edta. Various 1,3-dioxolanes showed a different behaviour in dependence on the N-substituent. With simple aliphatic moieties mainly dehydrogenated but hydrolyzed products were received. These enaminones were also available from the dehydrogenations of the corresponding 4-piperidones. Similar applied to para-acyl-aromatic substituted derivatives but with less yields. Aromatic substituents bearing a neighbour group on ortho-position with participation gave rise to different oxidation products partially with preservation of the ketal structure.

Design, synthesis, and biological evaluation of novel 4-substituted 1- methyl-1,2,3,6-tetrahydropyridine analogs of MPTP

The exceptionally good MAO-B substrate properties of several 1-methyl-4- phenyl-1,2,3,6-tetrahydropyridine (MPTP) derivatives have prompted studies to evaluate the corresponding properties of tetrahydropyridines bearing heteroatom-linked groups at C-4. Th