13074-63-0

Usage

Synthesis Reference(s)

Tetrahedron, 47, p. 8587, 1991 DOI: 10.1016/S0040-4020(01)82402-9

InChI:InChI=1/C11H20O/c1-3-4-5-6-10-9(2)7-8-11(10)12/h9-10H,3-8H2,1-2H3

Upstream product

• 1128-08-1 dihydro-cis-jasmone 
• 98736-17-5 tetrahydropyrethrolone methyl ether 
• 87349-05-1 2-pentyl-3-methyl-1-trimethylsiloxycyclopentene 
• 917-64-6 methyl magnesium iodide 
• 25564-22-1 2-pentyl-2-cyclopenten-1-one 
• 51916-48-4 undecane-2,5-diol 
• 28797-01-5 2-(2',4'-Pentadienyl)-3-methyl-2-cyclopentene-1-one-4-ol 
• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 128893-59-4 4-Methyl-5-oxo-decanenitrile 
• 24852-03-7 2-Ethoxycarbonyl-2-pentyl-1-cyclopentanone 
• 4819-67-4 2-pentyl-cyclopentanone 
• 24851-93-2 2-pentylcyclopent-1-en-1-yl acetate 
• 110-53-2 1-Bromopentane 
• 87326-04-3 3-(1-tetrahydropyranyloxycyclopropyl)-2-octene 

Downstream Products

• 142-62-1 hexanoic acid 
• 1128-08-1 dihydro-cis-jasmone 
• 110-15-6 succinic acid 
• 123-76-2 levulinic acid 

Relevant academic research and scientific papers

Al-NiCl(2°)6H2O-THF: A new, mild and neutral system for selective reduction of organic functional groups

A mild and neutral reducing system consisting of Al-NiCl(2°)6H2O-THF has been developed and reacted with a series of organic compounds containing different functional groups in order to evaluate its synthetic utility. It was observed that this system very efficiently reduces the α-enones to the saturated ketones, aromatic aldehydes and ketones to the corresponding alcohols, nitriles and nitroarenes to amines, acid anhydrides and acid chlorides to aldehydes, disulphides to thiols and epoxides to the corresponding alcohols. On the other hand isolated double bonds, carboxylic acids, esters, lactones, primary, benzyl and allyl halides, aliphatic aldehydes and ketones and aliphatic nitro compounds were found to remain inert to this system. Furthermore, the reducing properties of Al-NiCl(2°)6H2O in several other organic solvents were also studied.

ELECTROREDUCTIVE INTRAMOLECULAR COUPLING OF γ- AND δ-CYANOKETONES

Electroreduction of γ- and δ-cyanoketones in i-PrOH gave cyclized products α-hydroxyketones and their dehydroxylated ketones, and this reaction was applied to the synthesis of dihydrojasmone, methyl dihydrojasmonate, and Rosaprostol.

A simple procedure for selective reduction of α,β-unsaturated carbonyl compounds using Al-NiCl2 system

A combination of aluminium and nickel chloride in THF has been shown to effect the selective reduction of the olefinic double bond of the α-enone system. Isolated double bonds and aliphatic carbonyls remain unaffected under these conditions. However, aromatic aldehydes and ketones are converted to the corresponding hydroxy compounds by this system in good yields.

CYCLOPENTENONES FROM 1,2-DISILOXYCYCLOBUTENE VIA SILYLATED 1-VINYLCYCLOPROPANOLS. APPLICATION TO THE SYNTHESIS OF DIHYDROJASMONE AND CIS-JASMONE

An effective synthesis of 2,3-disubstituted 2-cyclopentenones involves C4 - C3 ring contraction of the readily available 1,2-disiloxycyclobutene followed by thermal C3 - C5 ring enlargement of trimethylsiloxyvinyl-cyclopropanes.To illustrate the convenience of this new approach the total syntheses of 2-methyl-3-p-tolyl-2-cyclopentenone, dihydrojasmone, and cis-jasmone are reported.

CHEMO- AND REGIOSELECTIVITIES IN ACID-CATALYZED RING EXPANSION OF 1-(1-METHYLSULFINYL-1-(METHYLTHIO)ALKYL)CYCLOBUTANOL DERIVATIVES

A new ring expansion of the title compounds catalyzed by an acid was studied.The reaction of 2-methyl-1-(1-methylsulfinyl-1-(methylthio)alkyl)cyclobutanol was regio- and chemoselective to afford 3-methyl-2-(methylthio)cyclopentanone derivative.