70855-13-9

Usage

Usage

Building block in the synthesis of pharmaceuticals and other organic compounds

Physical State

Yellow crystalline solid

Odor

Faint

Solubility

Soluble in organic solvents such as ethanol and acetone

Applications

a. Starting material in the production of various pharmaceuticals
b. Used in the synthesis of anti-inflammatory and analgesic drugs
c. Employed as a reagent in organic synthesis for the formation of complex organic molecules
d. Used in the production of fragrances and flavorings due to its aromatic properties

Industries

Pharmaceutical, chemical, and food industries

InChI:InChI=1/C13H16O2/c1-10-5-3-4-6-12(10)9-13(15)8-7-11(2)14/h3-6H,7-9H2,1-2H3

Upstream product

• 70855-12-8 2-Methyl-5-<(4-methylphenyl)methyl>furan 
• 92631-28-2 1-(4-methylphenyl)-5-hexen-2-one 
• 201230-82-2 carbon monoxide 
• 78-94-4 methyl vinyl ketone 
• 104-82-5 4-Methylbenzyl chloride 
• 136028-33-6 diethyl (4-chloro-1-methylthio-3-pentenyl)phosphonate 
• 104-87-0 4-methyl-benzaldehyde 
• 92631-27-1 6-p-tolylhex-1-en-5-ol 
• 104-09-6 4-methylphenylacetaldehyde 
• 104-81-4 4-Methylbenzyl bromide 
• 534-22-5 2-methylfuran 
• 105938-95-2 (Z)-4-Chloro-5-p-tolyl-pent-3-enoic acid 
• 72538-33-1 2-p-tolylnitroethane 
• 7559-36-6 4-methyl-β-nitrostyrene 

Downstream Products

• 70855-14-0 3-methyl-2-(4-methylphenyl)-2-cyclopenten-1-one 
• 75207-30-6 Methanesulfonic acid 1-[2-(2-methyl-[1,3]dithiolan-2-yl)-ethyl]-2-p-tolyl-propyl ester 
• 75207-28-2 6,6-(ethylenedithio)-2-p-tolylheptan-3-one 
• 75207-29-3 6,6-(ethylenedithio)-3-hydroxy-2-p-tolylheptane 
• 75207-31-7 6,6-(ethylenedithio)-2-p-tolylhept-2-ene 
• 75207-32-8 2-p-tolylhept-2-en-6-one 
• 75207-34-0 6-(4-methylphenyl)-2-heptanone 
• 55873-31-9 3,3-dimethyl-2-p-tolylcyclopentenone 

Relevant academic research and scientific papers

Pd(0)-Catalyzed Conjugate Addition of Benzylzinc Chlorides to α,β-Enones in An Atmosphere of Carbon Monoxide: Preparation of 1,4-Diketones

Pd(0)-catalyzed conjugate addition of benzylzine chloride to methyl vinyl ketone in the presence of chlorotrimethylsilane and lithium chloride in an atmosphere of carbon monoxide at room temperature afforded 1-phenyl-2,5-hexanedione monosilyl enol ether. In this catalytic carbonylation, four components are connected in one reaction. Successive acidic workup generated a variety of 1,4-diketones from substituted benzylzine chlorides or related compounds and α,β-enones. Some products were converted to cyclopentenones or five-membered heterocyclic compounds containing an N, O, or S atom.

A convenient synthesis of 1,4-diketones

A simple and short synthesis of 1,4-diketones was achieved via 2-chloro-5-methylthio-2,5-hexadienes and their hydrolysis with titanium tetrachloride.

A facile synthesis of 1,4-diketones

1,4-Diketones may conveniently be synthesized by the addition of 2-methylcyclopropenyllithium to N-methoxy-N-methylcarboxamides followed by hydrolysis of intermediate cyclopropyl ketone adducts on silica gel. The new method has been applied to the synthesis of cis-jasmone.

One-Step Synthesis of 1,4-Diketones by Nucleophilic Reaction to Tricarbonyl Complexes of α,β-Unsaturated Ketones

Tricarbonyliron complexes of 3-buten-2-one, 3-penten-2-one, and 4-phenyl-3-buten-2-one reacted with organolithium and Grignard reagents to afford 1,4-diketones in one step, some of the products are amenable to convertion to natural products.

AN IMPROVED, SIMPLE SYNTHESIS OF 3-METHYL-2-(4-METHYLPHENYL) CYCLOPENTEN-2-ONE: AN IMPORTANT INTERMEDIATE IN CUPARENE SYNTHESIS

Conjugate addition of phenyl-1-methyl-4-(2-nitroethyl) to methyl vinyl ketone in presence of basic alumina, following by Nef reaction and basic cyclization, affords 3-methyl-2-(4-methyl phenyl) cyclopenten-2-one in good yield.

Synthetic Studies on Aromatic Sesquiterpenoids: Synthesis of Curcumene Ether by Olefin Cyclisation

The acid-catalysed cyclisation of the olefinic β-hydroxy sulphides (15a) and (15b) gave 3-phenylthiocurcumene ether as a diastereoisomeric mixture together with 5,5-dimethyl-4-phenylthio-1-p-tolylcyclohex-1-ene (16) and 2-methyl-3-(1-methyl-1-phenylthioethyl)-2-p-tolylcyclobutan-1-ol (19).The diastereoisomers (17) and (18) were converted into curcumene ether (24).Treatment of the silyl enol ether (7) with benzenesulphenyl chloride yielded 5-phenylthiomethyl-2-tetrahydrofuran (8) and 5-chloro-1,6-bis(phenylthio)-1-p-tolylhexan-2-one (9). 1-p-Tolylhexane-2,5-dione (10) was also synthesised from (5) employing a palladium-catalysed oxidation, and this result constitutes a formal total synthesis of cuparene (11).

A CONVENIENT METHOD FOR THE SYNTHESIS OF 4-CHLORO-3-ALKENOIC ACID, A NEW USEFUL SYNTHETIC BLOCK FOR 4-OXOALKANOIC AND 4-OXO-2-ALKENOIC ACIDS

Easily available material, β-(1-chlorovinyl)-β-propiolactone reacted with organocopper reagents to afford 4-chloro-3-alkenoic acids in high yields.The acids were easily transformed into two kinds of useful carboxylic acids such as 4-oxoalkanoic and 4-oxo-(E)-2-alkenoic acids leading to various natural products.

A Simple and Efficient Total Synthesis of the Sesquiterpenes Cuparene and Iso-α-curcumene, from Furan Derivatives

3,3-Dimethyl-2-p-tolylcyclopentanone (7) was synthesised by 1,4-addition of lithium dimethylcuprate to 3-methyl-2-p-tolylcyclopentenone (6), which was derived from 5-methyl-2-(4-methylbenzyl)furan (4) through the diketone (5).Starting from the same intermediate (5), 2-p-tolylheptan-6-one (16) was also synthesised.These results constitute formal total syntheses of cuparene (9) and iso-α-curcumene (17) respectively.