5176-32-9

Basic information

• Product Name: 3-methyl-1-(4-methylphenyl)-1,2-diaza-3-azoniacyclopent-3-en-5-one
• Synonyms: 3-methyl-1-(4-methylphenyl)-1,2-diaza-3-azoniacyclopent-3-en-5-one;tert-butyl-1,2,3,4-tetrahydro-naphthalen-1,4-imine-9-carboxylate;1-methyl-3-(4-methylphenyl)-2H-1,2,3-triazol-1-ium-4-one;1-methyl-3-(4-methylphenyl)-2H-triazol-1-ium-4-one;1,2,3,4-Tetrahydronaphthalen-1,4-imine-9-carboxylic acid tert-butyl ester;Naphthalen-1,4-iMine-9-carboxylic acid, 1,2,3,4-tetrahydro-, 1,1-diMethylethyl ester;3-methyl-1-(4-methylphenyl)-1,2-diaza-3-azoniacyclopent-3-en-5-one-4
• CAS NO: 5176-32-9
• Molecular Formula: C10H12N3O+
• Molecular Weight: 245.32
• Mol File: 5176-32-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 41-42℃
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.150
• CAS DataBase Reference: 3-methyl-1-(4-methylphenyl)-1,2-diaza-3-azoniacyclopent-3-en-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methyl-1-(4-methylphenyl)-1,2-diaza-3-azoniacyclopent-3-en-5-one(5176-32-9)
• EPA Substance Registry System: 3-methyl-1-(4-methylphenyl)-1,2-diaza-3-azoniacyclopent-3-en-5-one(5176-32-9)

Safety Data

• Hazardous Substances Data: 5176-32-9(Hazardous Substances Data)

Usage

General Description

3-methyl-1-(4-methylphenyl)-1,2-diaza-3-azoniacyclopent-3-en-5-one is a chemical compound with a complex and lengthy name. It is classified as a diaza compound, which means it contains two nitrogen atoms within its molecular structure. This molecule is a cyclic structure with a five-membered ring, and it contains a methyl group and a 4-methylphenyl group attached to different carbon atoms within the ring. The compound also contains a keto group, indicating the presence of a carbonyl functional group. The specific properties and uses of this compound would depend on its specific reactivity, stability, and potential applications in various industrial and scientific fields.

InChI:InChI=1/C10H11N3O/c1-8-3-5-9(6-4-8)13-10(14)7-12(2)11-13/h3-7H,1-2H3/p+1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 1072-85-1 o-fluorobromobenzene 
• 118-92-3 anthranilic acid 
• 5176-27-2 N-tert-butyloxycarbonyl-pyrrole 
• 5176-28-3 N-(tert-butoxycarbonyl)-1,4-dihydro-1,4-iminonaphthalene 

Downstream Products

• 5176-31-8 1,2,3,4-tetrahydro-1,4-iminonaphthalene hydrochloride 
• 942491-77-2 2,2,2-trifluoro-1-(1,2,3,4-tetrahydro-1,4-epiminonaphth-9-yl)ethanone 
• 55257-99-3 N-methyl-1,2,3,4-tetrahydro-1,4-iminonaphthalene 
• 5176-30-7 1,2,3,4-tetrahydro-1,4-epiminonaphthalene 

Relevant articles and documents

COMPOUNDS AND COMPOSITIONS FOR TREATING CNS DISORDERS

The present disclosure provides compounds and pharmaceutical compositions thereof. Methods of making and using the compounds are also provided. The compounds can be used for the treatment, prevention, diagnosis and/or management of various CNS disorders.

7-Azabicyclo[2.2.1]heptane as a structural motif to block mutagenicity of nitrosamines

Nitrosamines are potent carcinogens and toxicants in the rat and potential genotoxins in humans. They are metabolically activated by hydroxylation at an α-carbon atom with respect to the nitrosoamino group, catalyzed by cytochrome P450. However, there has been little systematic investigation of the structure-mutagenic activity relationship of N-nitrosamines. Herein, we evaluated the mutagenicity of a series of 7-azabicyclo[2.2.1]heptane N-nitrosamines and related monocyclic nitrosamines by using the Ames assay. Our results show that the N-nitrosamine functionality embedded in the bicyclic 7-azabicylo[2.2.1]heptane structure lacks mutagenicity, that is, it is inert to α-hydroxylation, which is the trigger of mutagenic events. Further, the calculated α-C-H bond dissociation energies of the bicyclic nitrosamines are larger in magnitude than those of the corresponding monocyclic nitrosamines and N-nitrosodimethylamine by as much as 20-30 kcal/mol. These results are consistent with lower α-C-H bond reactivity of the bicyclic nitrosamines. Thus, the 7-azabicyclo[2.2.1]heptane structural motif may be useful for the design of nongenotoxic nitrosamine compounds with potential biological/medicinal applications.

An Evaluation of Amide Group Planarity in 7-Azabicyclo[2.2.1]heptane Amides. Low Amide Bond Rotation Barrier in Solution

Here we show that amides of bicyclic 7-azabicyclo[2.2.1]heptane are intrinsically nitrogen-pyramidal. Single-crystal X-ray diffraction structures of some relevant bicyclic amides, including the prototype N-benzoyl-7-azabicyclo[2.2.1]heptane, exhibited nitrogen-pyramidalization in the solid state. We evaluated the rotational barriers about the amide bonds of various N-benzoyl-7-azabicyclo[2.2.1]heptanes in solution. The observed reduction of the rotational barriers of the bicyclic amides, as compared with those of the monocyclic pyrrolidine amides, is consistent with a nitrogen-pyramidal structure of 7-azabicyclo[2.2.1]heptane amides in solution. A good correlation was found between the magnitudes of the rotational barrier of N-benzoyl-7-azabicyclo[2.2.1]heptanes bearing para-substituents on the benzoyl group and the Hammett's σp+ constants, and this is consistent with the similarity of the solution structures. Calculations with the density functional theory reproduced the nitrogen-pyramidal structures of these bicyclic amides as energy minima. The calculated magnitudes of electron delocalization from the nitrogen nonbonding nN orbital to the carbonyl π* orbital of the amide group evaluated by application of the bond model theory correlated well with the rotational barriers of a variety of amides, including amides of 7-azabicyclo[2.2.1]heptane. The nonplanarity of the amide nitrogen of 7-azabicyclo[2.2.1]heptanes would be derived from nitrogen-pyramidalization due to the CNC angle strain and twisting of the amide bond due to the allylic strain.