21856-74-6

Usage

Physical state

Yellowish to brown crystalline solid

Use in organic synthesis

As a ligand for metal catalysts

Industrial application

Widely used in the pharmaceutical industry for the production of various drugs and as a key intermediate in the synthesis of various bioactive compounds

Potential properties

Studied for its potential anticancer, anti-inflammatory, and antioxidant properties

Other uses

Used in the production of dyes, perfumes, and other specialty chemicals.

InChI:InChI=1/C22H22O/c23-22-20(16-18-10-4-1-5-11-18)14-8-3-9-15-21(22)17-19-12-6-2-7-13-19/h1-2,4-7,10-13,16-17H,3,8-9,14-15H2/b20-16+,21-17+

Upstream product

• 502-49-8 cycloactanone 
• 100-52-7 benzaldehyde 
• 108-94-1 cyclohexanone 

Downstream Products

• 34403-32-2 trans-2,8-Dibenzylcyclooctanon 
• 77109-65-0 4-Phenyl-10-[1-phenyl-meth-(E)-ylidene]-5,6,7,8,9,10-hexahydro-4H-1-thia-3a,11-diaza-cycloocta[f]inden-3-one 
• 77109-77-4 5-Phenyl-11-[1-phenyl-meth-(E)-ylidene]-2,3,6,7,8,9,10,11-octahydro-5H-1-thia-4a,12-diaza-cycloocta[b]naphthalen-4-one 
• 34403-32-2 cis-2,8-Dibenzylcyclooctanon 
• 77109-59-2 4-Phenyl-10-[1-phenyl-meth-(E)-ylidene]-3,4,5,6,7,8,9,10-octahydro-1H-cyclooctapyrimidine-2-thione 

Relevant academic research and scientific papers

Claisen-schmidt condensation catalyzed by metal-organic frameworks

Metal-organic framework [Fe(BTC) (BTC = 1,3,5-benzenetricarboxylic acid)] is a convenient heterogeneous catalyst for the carbon-carbon bond forming reaction in toluene between acetophenone and benzaldehyde to give selectively chalcone in high yield. Fe(BTC) appears as a general catalyst able to synthesize selectively different chalcone derivatives bearing various functionalities. Fe(BTC) could be recycled with no significant loss of catalytic efficiency and crystallinity in subsequent runs.

The synthesis and chlorosulfonation of some diarylidene and heteroarylidene ketones with varying alicyclic ring size

A series of diarylidene and heteroarylidene ketones (1-20) was prepared using alicyclic ketones ((CH2)nC=O where n=3 to 7).An improved synthesis of 2,4-dibenzylidenecyclobutanone (1) is described and the ease of preparation of the arylidene derivatives is considered in terms of the size of the alicyclic ring.Treatment of 2,5-dibenzylidenecyclopentanone (2) with chlorosulfonic acid (10 mole equivalents) afforded the 4,4'-bis-sulfonyl chloride (23), reducing the amount of chlorosulfonis acid (6 mole equivalents) produced the corresponding mono-sulfonyl chloride (24).Only the respective 4,4'-bis-sulfonyl chlorides (39, 45, 51) could be isolated from the diarylidene ketones derived from larger alicyclic rings.Attempted chlorosulfonation of 2,4-dibenzylidene cyclobutanone (1) gave a mixture of products which could not be clearly characterised.The sulfonyl chlorides were converted into stable sulfonamides (25-29, 35, 36, 38, 40-44, 46-48, 52, 54) by condensation with amines, and selected samples were screened for biological activity as potential insecticides, herbicides, and fungicides.The orientation of sulfonation is discussed in relation to stereoelectronic factors and the relevant spectral data.Key words: Arylidene and heteroarylidene ketones, chlorosulfonation, sulfonamides

Reactions with (Arylmethylene)cycloalkanones. 3. Synthesis of 11-(Arylmethylene)octahydrocyclooctathiazolopyrimidin-3-one Derivatives of Expected Biological Activity

Cyclooctapyrimidine-2-thiones (II) were prepared by heating 2,8-bis(arylmethylene)cyclooctanones with thiourea in ethanolic potassium hydroxide.Compounds II reacted with chloroacetic acid to yield the title compounds (III).The 2,11-bis(arylmethylene) d