7053-79-4

Usage

InChI:InChI=1/C12H18O2/c1-8(2)11-6-5-9(3)12(7-11)14-10(4)13/h5,11-12H,1,6-7H2,2-4H3/t11-,12+/m1/s1

Upstream product

• 80-56-8 rac-α-pinene 
• 64-19-7 acetic acid 
• 1197-06-4 cis-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol 
• 75-36-5 acetyl chloride 
• 1253216-40-8 (5S)-2-methyl-5-(1-methylvinyl)-2-cyclohexen-1-ol 
• 581-55-5 benzylidene 1,1-diacetate 
• 5989-54-8 (-)-(S)-limonene 
• 108-24-7 acetic anhydride 
• 99-49-0 Carvone 
• 557-34-6 zinc diacetate 
• 30808-80-1 trans-6-chloro-p-mentha-1,8-diene 
• 99-48-9 (4R,6R)-carveol 
• 57022-47-6 carveol methyl ether 

Downstream Products

• 344559-89-3 3-(5-Isopropenyl-2-methyl-2-cyclohexen-1-yl)-3-methyl-2-butanon 
• 88835-05-6 2-(5-Isopropenyl-2-methyl-2-cyclohexen-1-yl)-1-cyclohexanon 
• 99-48-9 (4R,6R)-carveol 
• 76704-28-4 (4S,6S)-6-Acetoxy-4-isopropenyl-1-methylcyclohexene 
• 138-86-3 limonene. 
• 88846-55-3 2-(5-Isopropenyl-2-methyl-2-cyclohexen-1-yl)-1-cyclopentanon 
• 344438-52-4 2-(5-Isopropenyl-2-methyl-2-cyclohexen-1-yl)-2,4-dimethyl-3-pentanon 
• 344443-62-5 1-(5-Isopropenyl-2-methyl-2-cyclohexen-1-yl)-3,3-dimethyl-2-butanon 
• 88835-04-5 2-(5-Isopropenyl-2-methyl-2-cyclohexen-1-yl)-3-pentanon 
• 344560-06-1 1-(5-Isopropenyl-2-methyl-2-cyclohexen-1-yl)-3-methyl-2-butanon 
• 74184-42-2 trans-2,3-dimethyl-5-isopropenylcyclohexene 
• 74153-17-6 cis-2,3-dimethyl-5-isopropenylcyclohexene 

Relevant academic research and scientific papers

Formyloxyacetoxyphenylmethane and 1,1-diacylals as versatile O-formylating and O-acylating reagents for alcohols

Formyloxyacetoxyphenylmethane, symmetric 1,1-diacylals and mixed 1-pivaloxy-1-acyloxy-1-phenylmethanes have been used as moisture stable O-formylating and O-acylating reagents for primary and secondary alcohols, allylic alcohols and phenols under solvent/catalyst free conditions to afford their corresponding esters in good yield.

Enantiomeric differentiation of oxygenated p-menthane derivatives by 13C NMR using Yb(hfc)3

The 13C NMR behaviour of 21 p-menthanic terpene bearing an oxygenated function (alcohol, ketone, acetate) was examined in the presence of a chiral lanthanide shift reagent (Yb(hfc)3). For each monocyclic compound, we measured the lanthanide-induced shift (LIS) on the signals of the carbons and the splitting of signals allowing the enantiomeric differentiation. Some general features were found about their LIS behaviour: experimental data establishing distinct patterns for carvomenthone-like compounds and menthone-like compounds. The enantiomeric splitting was observed for the majority of signals in the spectrum of each compound. In the case of alcohols and acetates, the influence of the relative stereochemistry (cis vs trans) of isopropyl(ene) and the binding function was discussed. Copyright

Microbial Allyl Rearrangement and Resolution of Acetates of Unsaturated Cyclic Terpene Alcohols by Pseudomonas sp. NOF-5 Strain

Microbial hydrolysis of the acetates of unsaturated cyclic terpene alcohols by Pseudomonas sp.NOF-5 isolated from soil was investigated. (+/-)-trans-Carveyl acetate ((+/-)-trans-3) was enantioselectively hydrolyzed with NOF-5 strain to give (-)-trans-carveol ((-)-trans-2 of 86.6percent optical purity).However, the hydrolysis of (+/-)-cis-3 was less enantioselective, while (+/-)-piperitylacetate ((+/-)-6, a cis and trans mixture) was hydrolyzed to give the (-)-trans- and (-)-cis-piperitols ((-)-trans-5 and (-)-cis-5) in a poor optical yield.In this case, other tert-alcohols, (+)-trans- and (-)-cis-2-p-menthen-1-ols ((+/-)-trans-7 and (-)-cis-7, were also produced.Furthermore, microbial and enzymic allyl rearrangements of (+)-trans-6 and (-)-trans-verbenylacetate ((-)-trans-11) were studied.Biological treatment of (+)-trans-6 and (-)-trans-11 with NOF-5 or its esterase gave (+)-trans- and (-)-cis-7 and (+)-cis-3-pinen-2-ol ((+)-cis-12), respectively.

CLEAVAGES OF ETHERS BY CHLOROTRIMETHYLSILANE AND ACETIC ANHYDRIDE

Methyl and benzyl ethers have been cleaved with a combination of reagents consisting of chlorotrimethylsilane and acetic anhydride containing a catalytic amount of concentrated sulfuric acid.Methylthiomethyl ethers yield the correponding acetoxymethyl ethers with chlorotrimethylsilane and acetic anhydride.Comparative study with the borontrifluoride etherate and acetic anhydride method of ether cleavage suggests that chlorotrimethylsilane and acetic anhydride (conc.H2SO4 catalysis) could be a useful alternative to it.

Reactions of d-Limonene with t-Butyl Hypochlorite

Investigation of the title reaction under different conditions of temperature, solvents and catalysis has led to its optimisation with respect to the yield of (-)-trans-carvyl chloride (2).Other products formed in the reaction have been identified as 1,2-dichloro-p-menth-8-ene (5), 10-chloro-p-mentha-1,8-diene (6), 2-chloro-p-mentha-1(7)8-diene (10) and 6,10-dichloro-p-mentha-1,8-diene (11).The reaction proceeds almost entirely by electrophilic halogenation with no evidence of competition from a radical mechanism.

NUCLEOPHILIC SUBSTITUTION OF ALKYL HALIDES BY ZINC SALTS-3 PREPARATION OF TERTARY ALKYL ESTERS AND ETHERS UNDER NON-SOLVOLYTIC CONDITIONS

Zinc salts of carboxylic acids, phenols and alcohols are found to react with tertiary alkyl halides in nonpolar solvents and in presence of a base yielding the corresponding esters and ethers in moderate to good yields.

Enzymic Resolution of (+/-)-Unsaturated Cyclic Terpene Alcohols via Asymmetric Hydrolysis of Corresponding Acetates by Microorganisms

Asymmetric hydrolysis of the acetates of (+/-)-cis and trans-carveols by microorganisms or their esterase produced chiral cis and trans-carveols and the acetates of their enantiomers.The enantioselectivity of the microbial hydrolysis and the optical purities of the products varied with the species of microorganisms.This method was also applied in separation of diastereomeric mixtures of (-)-carveols and (-)-7-epi-α-cyperols.