623-82-5

Usage

Chemical Properties

white to light yellow powder

InChI:InChI=1/C7H12O4/c1-5(4-7(10)11)2-3-6(8)9/h5H,2-4H2,1H3,(H,8,9)(H,10,11)/p-2/t5-/m1/s1

Upstream product

• 186581-53-3 diazomethane 
• 60-29-7 diethyl ether 
• 171598-61-1 (S)-methyl 5-chloro-3-methyl-5-oxopentanoate 
• 31558-25-5 2,6-dimethyl-2,3,8-octanetriol 
• 99356-87-3 (R)-5-cyano-4-methyl-valeric acid 
• 101084-14-4 3-methyl-1,6-adiponitrile 
• 51097-61-1 3-methylhexan-1,6-dial 
• 89-82-7 pulegone 
• 18951-85-4 (R)-citronellic acid 
• 151-50-8 potassium cyanide 
• 5208-51-5 (-)(1S:5S)-cis-1-Methyl-5-isopropenyl-cyclohex-3-en 
• 89-82-7 (+)-pulegone 
• 161029-67-0 (3R)-3-methylhept-6-enoic acid 
• 110659-28-4 (R)-(+)-5-acetoxy-4-methylpentanoic acid 

Downstream Products

• 6672-30-6 (R)-3-methylcyclopentanone 
• 1757-42-2 3-methyl-cyclopentanone 
• 1321624-40-1 (6R)-N-(4-methoxyphenyl)-N,2,6-trimethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-aminium chloride 
• 1402081-42-8 (R)-3-methyl-N¹,N⁶-diphenylhexanediamide 
• 1583281-98-4 C₁₉H₂₄O₅ 
• 1583281-12-2 C₁₅H₁₈O₃ 
• 82136-11-6 (R)-(+)-3-methylcyclopentanone 2,4-dinitrophenylhydrazone 

Relevant academic research and scientific papers

Enantioselective total synthesis of pinnaic acid and halichlorine

The enantioselective total synthesis of the bioactive marine natural products pinnaic acid and halichlorine is reported in detail. Our total synthesis features the construction of the five-membered ring and C9 and C13 stereogenic centers through a palladium-catalyzed trimethylenemethane [3+2] cyclization; the installation of the nitrogen atom through a regioselective Beckmann rearrangement of a poorly reactive ketone; the stereoselective cyclization of the spiro ring through a four-step, one-pot hydrogenation- cyclization; and efficient connection of the sterically hindered lower chain through a reduced-pressure cross olefin metathesis reaction. Copyright

Enantioselective baeyer-villiger oxidation: Desymmetrization of meso cyclic ketones and kinetic resolution of racemic 2-arylcyclohexanones

Catalytic enantioselective Baeyer-Villiger (BV) oxidations of racemic and meso cyclic ketones were achieved in the presence of chiral N,N'-dioxide-Sc III complex catalysts. The BV oxidations of prochiral cyclohexanones and cyclobutanones afforded series of optically active μ- and γ-lactones, respectively, in up to 99% yield and 95% ee. Meanwhile, the kinetic resolution of racemic 2-arylcyclohexanones was also realized via an abnormal BV oxidation. Enantioenriched 3-aryloxepan-2-ones, whose formation is counter to the migratory aptitude, were obtained preferentially. Both the lactones and the unreacted ketones were obtained with high ee values.

Enantioselective baeyer-villiger oxidation: Desymmetrization of meso cyclic ketones and kinetic resolution of racemic 2-arylcyclohexanones

Catalytic enantioselective Baeyer-Villiger (BV) oxidations of racemic and meso cyclic ketones were achieved in the presence of chiral N,N'-dioxide-Sc III complex catalysts. The BV oxidations of prochiral cyclohexanones and cyclobutanones afforded series of optically active μ- and γ-lactones, respectively, in up to 99% yield and 95% ee. Meanwhile, the kinetic resolution of racemic 2-arylcyclohexanones was also realized via an abnormal BV oxidation. Enantioenriched 3-aryloxepan-2-ones, whose formation is counter to the migratory aptitude, were obtained preferentially. Both the lactones and the unreacted ketones were obtained with high ee values.

Synthesis and AChE inhibitory activity of new chiral tetrahydroacridine analogues from terpenic cyclanones

This work describes the enantioselective synthesis of a new series of terpenic chiral 9-aminotetrahydroacridine analogues. Several chiral ketones were synthesized from natural monoterpenes in an optically active form and subjected to the cyclodehydration reactions with anthranilonitrile in the presence of BF3·Et2O as catalyst. The 9-aminotetrahydroacridine analogues were tested as acetylcholinesterase (AChE) inhibitors. Based on qualitative structure-activity relationship some trends are suggested.

An improved protocol for the oxidative cleavage of alkynes, alkenes, and diols with recyclable Ru/C

Efficient synthesis of carboxylic acids from alkynes; aldehydes from alkenes and diols employing Ru/C-based recyclable catalytic system is reported with good to excellent yields. Georg Thieme Verlag Stuttgart.

Supported ruthenium nanoparticle catalyst for cis -dihydroxylation and oxidative cleavage of alkenes

The present invention relates to the use of nanosized metal particles (e.g., ruthenium) grafted on inert solid support for oxidation of alkenes. The supported metal catalyst can effect cis-dihydroxylation and oxidative cleavage of alkenes to give the respective cis-diols and carbonyl products.

Ruthenium nanoparticles supported on hydroxyapatite as an efficient and recyclable catalyst for cis-dihydroxylation and oxidative cleavage of alkenes

Impregnation of hydroxyapatite with colloidal ruthenium results in the formation of a catalyst that effects cis-dihydroxylation and oxidative cleavage of alkenes to their respective cis-1,2-diols and carbonyl products in good to excellent yields (see scheme). The supported ruthenium catalyst can be easily recycled and reused for consecutive reaction runs without significant deterioration of the catalytic activities. R1, R2 = H, alkyl, aryl.

Osmium tetroxide-promoted catalytic oxidative cleavage of olefins: An organometallic ozonolysis

A mild, organometallic alternative to ozonolysis utilizing oxone and OsO4 is presented. This is a direct oxidation of olefins via the carbon-carbon cleavage of an osmate ester by the action of oxone. Twenty-four different olefins were converted to their corresponding ketones or carboxylic acids in high yields (> 80%). Free alcohols, acetate- and benzyl-protected alcohols, and 1,2-diols were stable under these conditions. This method should be applicable for traditional organic synthesis. Copyright

Ruthenium-catalyzed oxidative cleavage of olefins to aldehydes

Three oxidation protocols have been developed to cleave olefins to carbonyl compounds with ruthenium trichloride as catalyst (3.5 mol %). These methods convert olefins that are not fully substituted to aldehydes rather than carboxylic acids. While aryl olefins were cleaved to aromatic aldehydes in excellent yields by using the system of RuCl3-Oxone-NaHCO3 in CH3CN-H2O (1.5:1), aliphatic olefins were converted into alkyl aldehydes with RuCl3-NaIO4 in 1,2-dichloroethane-H2O (1:1) in good to excellent yields. It is noteworthy that terminal aliphatic olefins were cleaved to the corresponding aldehydes in excellent yields by using RuCl3-NaIO4 in CH3CN-H2O (6:1).