899-98-9

Basic information

• Product Name: 2,7-DIBENZYLIDENECYCLOHEPTANONE
• Synonyms: 2,7-DIBENZYLIDENECYCLOHEPTANONE;2,7-Bis(benzylidene)cycloheptane-1-one;2,7-Bisbenzylidenecycloheptanone
• CAS NO: 899-98-9
• Molecular Formula: C₂₁H₂₀O
• Molecular Weight: 288.3829
• Mol File: 899-98-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 481.5°Cat760mmHg
• Flash Point: 212.1°C
• Appearance: /
• Density: 1.125g/cm³
• Vapor Pressure: 1.99E-09mmHg at 25°C
• Refractive Index: 1.652
• CAS DataBase Reference: 2,7-DIBENZYLIDENECYCLOHEPTANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,7-DIBENZYLIDENECYCLOHEPTANONE(899-98-9)
• EPA Substance Registry System: 2,7-DIBENZYLIDENECYCLOHEPTANONE(899-98-9)

Safety Data

• Hazardous Substances Data: 899-98-9(Hazardous Substances Data)

Usage

General Description

2,7-Dibenzylideneheptanone is a chemical compound with the molecular formula C20H20O. It is a yellow to orange crystalline solid that is insoluble in water but soluble in organic solvents. 2,7-DIBENZYLIDENECYCLOHEPTANONE is commonly used as a chiral auxiliary in organic synthesis, particularly in the formation of chiral alcohols and amines. It is also used as a flavoring agent and fragrance in the food and cosmetic industries. Additionally, 2,7-Dibenzylideneheptanone has potential applications in medicinal chemistry as a building block for pharmaceutical compounds. However, it is important to handle this compound with caution, as it may be harmful if swallowed, inhaled, or absorbed through the skin, and it should be stored and handled in a well-ventilated area.

InChI:InChI=1/C21H20O/c22-21-19(15-17-9-3-1-4-10-17)13-7-8-14-20(21)16-18-11-5-2-6-12-18/h1-6,9-12,15-16H,7-8,13-14H2/b19-15+,20-16+

Upstream product

• 141-52-6 sodium ethanolate 
• 100-52-7 benzaldehyde 
• 502-42-1 cycloheptanone 
• 505-48-6 octane-1,8-dioic acid 

Downstream Products

• 1446347-90-5 (4S,9E)-2-amino-4,5,6,7,8,9-hexahydro-4-phenyl-9-(phenylmethylene)cyclohepta[b]pyran-3-carbonitrile 
• 1322199-58-5 9-benzylidene-4-phenyl-6,7,8,9-tetrahydro-5H-cycloheptapyrimidin-2-ylamine 
• 1289514-88-0 (R,E)-2-amino-9-benzylidene-4-phenyl-4,5,6,7,8,9-hexahydrocyclohepta[b]pyran-3-carbonitrile 
• 78159-39-4 2,7-dibenzyl-cycloheptanone oxime 
• 106695-86-7 2,7-Bis-diethylamino-2,7-bis-(diethylamino-phenyl-methyl)-cycloheptanone 
• 106721-61-3 1,6-Dimethyl-2,7-diphenyl-1,6-diaza-dispiro[2.1.2.4]undecan-4-one 
• 49709-10-6 2,7-dibenzylcycloheptanone 
• 103381-47-1 2,7-dibromo-2,7-bis-(α-bromo-benzyl)-cycloheptanone 

Relevant articles and documents

Synthesis, molecular modeling and bio-evaluation of cycloalkyl fused 2-aminopyrimidines as antitubercular and antidiabetic agents

An economical and efficient one step synthesis of a series of 8-(arylidene)-4-(aryl)-5,6,7,8-tetrahydro-quinazolin-2-ylamines and 9-(arylidene)-4-(aryl)-6,7,8,9-tetrahydro-5H-cycloheptapyrimidin-2-ylamines by the reaction of bis-benzylidene cycloalkanones and guanidine hydrochloride in presence of NaH has been developed. All the synthesized compounds were evaluated against Mycobacterium tuberculosis H37Rv strain and the α-glucosidase and glycogen phosphorylase enzymes. Few of the compounds have shown interesting in vitro activity with MIC up to 3.12 μg/mL against M. tuberculosis and very good inhibition of α-glucosidase and glycogen phosphorylase enzymes. The most potent non toxic compound 40 exhibited about 58% ex vivo activity at MIC of 3.12 μg/mL. The present study opens a new gate to synthesize antitubercular agents for diabetic TB patients. In silico docking studies indicate that mycobacterial dihydrofolate reductase is the possible target of these compounds.

Simple access to α, β unsaturated ketones by acid-catalyzed solvent- free reactions

Various chalcones and dibenzylidene cycloalkanones were readily prepared in a few minutes with good yields by simply mixing aromatic aldehydes with substituted acetophenones or benzaldehyde with cycloalkanones in the presence of catalytic amounts of p-toluene sulfonic acid under focused microwave irradiation.

Synthesis and cytotoxic evaluation of some cyclic arylidene ketones and related oximes, oxime esters, and analogs

A number of arylidene derivatives of alicyclic ketones and some corresponding oximes, oxime esters, and related compounds were prepared as candidate cytotoxic agents. All of the compounds were evaluated against murine L1210 lymphoid leukemia cells. In general, cytotoxicity was greatest with the α,β-unsaturated ketones and diminished with the oximes, and the oxime esters had little or no activity in this screen. When the same compounds were examined in both the in vitro L1210 and P388 leukemia screens, in the majority of cases the L1210 cells were more sensitive to these derivatives. Over half of the compounds prepared were evaluated against approximately 55 human tumors in vitro and showed selective toxicity toward one or more groups of neoplastic diseases, particularly leukemia. Some correlations between structure and bioactivity were discerned. The cytotoxicity screening and stability studies of representative compounds suggested that the ketones, oximes, and oxime esters were stable under the conditions of bioevaluation. X-ray crystallography of four representative compounds revealed structural features associated with cytotoxicity which may be considered in the design of future candidate cytotoxins.