100381-49-5

Basic information

• Product Name: 1-(cyclohex-1-enyl)-1,3-dihydro-2H-benzimidazol-2-one
• Synonyms: 1-(cyclohex-1-enyl)-1,3-dihydro-2H-benzimidazol-2-one
• CAS NO: 100381-49-5
• Molecular Weight: 214.267
• Mol File: 100381-49-5.mol

Chemical Properties

• CAS DataBase Reference: 1-(cyclohex-1-enyl)-1,3-dihydro-2H-benzimidazol-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(cyclohex-1-enyl)-1,3-dihydro-2H-benzimidazol-2-one(100381-49-5)
• EPA Substance Registry System: 1-(cyclohex-1-enyl)-1,3-dihydro-2H-benzimidazol-2-one(100381-49-5)

Safety Data

• Hazardous Substances Data: 100381-49-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(cyclohex-1-enyl)-1,3-dihydro-2H-benzimidazol-2-one is used as a pharmaceutical compound for its anti-inflammatory, antifungal, and anticancer properties. 1-(cyclohex-1-enyl)-1,3-dihydro-2H-benzimidazol-2-one's diverse biological activities make it a promising candidate for the development of new drugs to treat various health conditions.
Used in Agricultural Industry:
In the agricultural sector, 1-(cyclohex-1-enyl)-1,3-dihydro-2H-benzimidazol-2-one is used as a bioactive compound for its potential antifungal properties. It may be utilized in the development of new fungicides to protect crops from fungal infections, thereby enhancing crop yield and quality.

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 3190-03-2 1,3-dihydrospiro[2H-benzimidazole-2,1'-cyclohexane] 
• 95-54-5 1,2-diamino-benzene 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 

Relevant articles and documents

Efficient and simple synthesis of novel 1,2,3-triazolyl-linked benzimidazolone, molecular docking and evaluation of their antimicrobial activity

In this study, a novel series of 1,2,3-triazolyl-benzimidazolone derivatives have been synthesized by click reaction of azides with benzimidazolones 2a–b. The latter compounds were prepared with excellent yields (85–97%), the structures of products were determined by spectral analysis. Then, the X-rays crystallographic analysis of compound 7a revealed the self-assembling properties. The new heterocycles were evaluated for their in?vitro antimicrobial activities against Gram-positive and Gram-negative bacteria and against fungi strains. The most tested synthesized compounds showed potent antibacterial and antifungal activities against all tested strains. The compound 6c was found to be the most active, particularly, against Aspergillus niger and Penicillium sp. with the same MIC and MBC of 0.0625 mg/mL. Furthermore, in silico molecular docking studies stipulated a sign of a good correlation between experimental activity and calculated binding affinity. According to the docking results, compound 6d showed minimum binding energy and can be considered as a good antimicrobial agent.

Synthesis, characterization and X-ray structure of heterocyclic systems prepared via 1,3-dipolar cycloaddition of nitrile oxides with benzimidazolone

We report here a one-step synthesis of the new isoxazolyl-benzimidazolones and isoxazolinyl-benzimidazolones by 1,3-dipolar cycloaddition of the p-substituted benzonitrile oxides and mesitonitrile oxide with 1-cyclohex-1-en-1-yl-3-propargyl-benzimidazolone or 1-cyclohex-1-en-1-yl-3-allyl-benzimidazolone. In all cases these cycloadditions are completely regio- and chemoselective. The structures of new cycloadducts obtained are elucidated by their analytical and spectral data. The relative stereochemistry of the cycloadduct 8 was confirmed by single crystal X-ray analysis.

Microwave-assisted domino benzannulation of α-Oxo Ketenes: Preparation of 1,3-Dihydro-2H-1,5-benzodiazepin-2-ones

The microwave irradiation of a series of 2-diazo-1,3-diketones in the presence of an o-phenylenediamine derivative triggered a domino Wolff rearrangement/nucleophilic addition/intramolecular imination sequence to provide a new synthetic entry to 1,3-dihydr-2H-1,5-benzodiazepin-2-ones, a class of molecules with important biological properties. The microwave-assisted reactions of 2-diazo-1,3-diones and o-phenylenediamines in the absence of additives furnished bi-and tricyclic 1,3-dihydro-2H-1,5-benzodiazepin-2-ones by a domino Wolff rearrangement/nucleophilic addition/intramolecular imination sequence with the formation of three new covalent bonds. This reaction is a new and complementary synthetic approach to a class of "drug-like" compounds.

Rearrangement of spiro-benzimidazolines: preparation of N-alkenyl- and N-alkyl-benzimidazol-2-ones

A synthetically useful protocol has been developed for the preparation of highly functionalized N-alkenyl-benzimidazol-2-ones. Reaction of commercially available o-phenylenediamines with variously substituted cyclic ketones provides spiro-benzimidazolines. Treatment of these spiro-benzimidazolines with triphosgene in the presence of potassium carbonate results in rapid rearrangement and formation of N-alkenyl-benzimidazol-2-ones in modest to excellent yield for the two-step sequence. Extension of this methodology toward the preparation of a μ opiate receptor antagonist and droperidol, a potent antiemetic and antipsychotic agent, currently a marketed pharmaceutical is also described. Upon treatment of spiro-benzimidazolines with triphosgene in the presence of sodium triacetoxyborohydride, N-alkyl-benzimidazol-2-ones were formed.