100847-96-9

Usage

InChI:InChI=1/C13H16O3/c1-10-6-8-11(9-7-10)12(14)4-2-3-5-13(15)16/h6-9H,2-5H2,1H3,(H,15,16)

Upstream product

• 1071-71-2 ethyl 6-chloro-6-oxohexanoate 
• 111-50-2 Adipic acid dichloride 
• 108-88-3 toluene 
• 2035-75-8 adipic anhydride 
• 117421-36-0 6-oxo-6-(p-tolyl)hexanal 
• 1821-24-5 1-(p-methylphenyl)cyclohexanol 
• 627-91-8 adipic acid monomethyl ester 
• 5720-05-8 4-methylphenylboronic acid 
• 822-87-7 2-Chlorocyclohexanone 
• 52776-14-4 2-(4-methylphenyl)cyclohexanone 
• 106-38-7 para-bromotoluene 
• 1821-23-4 1-cyclohex-1-enyl-4-methylbenzene 
• 21666-91-1 (+/-)-trans-2-(4-methylphenyl)cyclohexanol 
• 64-19-7 acetic acid 

Downstream Products

• 91202-39-0 6-oxo-6-p-tolylhexanoic acid methyl ester 
• 100847-87-8 ethyl 6-oxo-6-p-tolylhexanoate 
• 106696-60-0 5-(p-toluoyl)valeroyl chloride 
• 124016-77-9 6-(4-methylphenyl)heptanoic acid 
• 124016-87-1 6-(3-Amino-4-methyl-phenyl)-6-oxo-hexanoic acid 
• 124016-88-2 6-(3-Hydroxy-4-methyl-phenyl)-6-oxo-hexanoic acid 
• 124034-05-5 6-(3-Amino-4-methyl-phenyl)-heptanoic acid 
• 124016-83-7 6-(3-Hydroxy-4-methyl-phenyl)-heptanoic acid 
• 124016-76-8 6-hydroxy-6-(4-methylbenzoyl)heptanoic acid 
• 124016-75-7 6-(3-methoxy-4-methylphenyl)heptanoic acid 
• 124016-82-6 6-(4-Methyl-3-nitro-phenyl)-heptanoic acid 
• 124016-86-0 6-(4-Methyl-3-nitro-phenyl)-6-oxo-hexanoic acid 
• 62315-35-9 6-p-tolylhexanoic acid 
• 100847-93-6 Ethyl 2-methyl-2-(4-methylphenyl)cyclopentane carboxylate 

Relevant academic research and scientific papers

Selective C-C Bond Cleavage of Cycloalkanones by NaNO2/HCl

A novel selective fragmentation of cycloalkanones by NaNO2/HCl has been established. The C-C bond cleavage reaction proceeds smoothly under mild conditions, selectively affording versatile keto acids or oxime acids. The methodology can streamline the synthesis of valuable chiral molecules and isocoumarins from readily available feedstocks.

Visible Light-Driven, Copper-Catalyzed Aerobic Oxidative Cleavage of Cycloalkanones

A visible light-driven, copper-catalyzed aerobic oxidative cleavage of cycloalkanones has been presented. A variety of cycloalkanones with varying ring sizes and various α-substituents reacted well to give the distal keto acids or dicarboxylic acids with moderate to good yields.

Solid-supported cross-metathesis and a formal alkane metathesis for the generation of biologically relevant molecules

Solid-phase synthetic strategies toward the generation of libraries of biologically relevant molecules were developed using olefin cross-metathesis as a key step. It is remarkably the formal alkane metathesis based on a one-pot, microwave-assisted, ruthenium-catalyzed cross-metathesis and reduction to obtain Csp3-Csp3 linkages.

Alkylarylketo acids

Disclosed are novel alkylarylketocarboxylic acids and 5-substituted tetrazoles represented by the formula STR1 wherein Z is aryl or an alkyl of the structure STR2 W is a carboxyl moiety or a tetrazole moiety bound to Z at the 5-position of the tetrazole; R1 is C4 -C12 alkyl where Z is aryl and X is oxygen or is C5 -C12 alkyl where Z is alkyl and where Z is aryl and X is a bond; R2 and R3 are each independently hydrogen, C1 -C4 alkyl, hydroxy, C1 -C4 alkoxy, halogen, trihalomethyl, nitro, cyano or C1 -C4 acyl; R4, R5, R6 and R7 are each independently hydrogen or C1 -C4 alkyl or R4 and R6 or R5 and R7 can combine to form a carbocyclic ring; X is oxygen, or a bond at the ortho or para position; m is 0, 1 or 2; and n is 0 or 1, and nontoxic, pharmaceutically acceptable addition salts and carboxylic acid esters thereof.

Synthesis of 2-hydroxy-3,6,10-trimethylbenzocyclooct-5-ene (isoparvifolin), a sesquiterpenic benzocyclooctene

The synthesis of 2-hydroxy-3,6,10-trimethylbenzocyclooct-5-ene (2) (isoparvifolin), a double bond isomer of the naturally occuring phenolic sesquiterpene (1) (parvifolin) is described.The key intermediate, 6-(3-methoxy-4-methylphenyl)heptanoic acid (3), required for the synthesis of 2 has been made from the keto ester (4) in two ways (4 -> 5 -> 6 -> 7 -> -> 3; 4-> -> 8 -> -> 3).The methoxyaryl heptanoic acid (3) is cyclodehydrated to the benzocyclooctanone (9).Vilsmeier reaction on the corresponding benzocyclooctanol, obtained by NaBH4 reduction of 9 gives the unsaturated aldehyde (10).Two functional group transformations on 10 (CHO -> CH3 and OCH3 -> OH) by standard procedures finally yield isoparvifolin (2).

SYNTHESIS OF AROMATIC SESQUITERPENES, (+/-)-CUPARENE AND (+/-)-LAURENE BY MEANS OF AN INTRAMOLECULAR CARBENOID DISPLACEMENT (ICD) REACTION

The synthesis of (+/-)-cuparene and (+/-)-laurene was accomplished by means of an intramolecular carbenoid displacement (ICD) reaction of the benzyl sulphide (12) as a key reaction.

Synthesis of an Aromatic Sesquiterpene, (+/-)-Cuparene, via Construction of a Quaternary Carbon Centre by an Intramolecular Carbenoid Displacement Reaction

The synthesis of (+/-)-cuparene (11), which includes as the key step an intramolecular carbenoid displacement reaction at the benzylic position of a benzyl sulphide derivative, is described.