74185-00-5

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 10458-14-7 (2R,5S)-menthone 
• 89-80-5 p-menthan-2-one 
• 412324-05-1 (3R,6S)-6-Isopropyl-3-methyl-cyclohex-1-enol 
• 72311-09-2 3-Methyl-6-(1-methylethyl)-1-trimethylsilyloxy-1-cyclohexen 
• 59781-47-4 r-2-Acetyl-t-3-methyl-c-6-(1-methylethyl)-1-cyclohexanon 

Downstream Products

• 929033-26-1 (2R,3R,6S)-2-bromo-3-methyl-6-(prop-2-yl)-cyclohexanone 
• 929033-27-2 (3S,6R)-1-bromo-2-methoxy-3-(prop-2-yl)-6-methylcyclohexene 
• 929032-87-1 (3'S,6'R)-4-hydroxy-4-(2'-methoxy-6'-methyl-3'-(prop-2-yl)-cyclohex-1-enyl)-2,3-dimethoxy-cyclobut-2-enone 
• 929032-89-3 (3'S,6'R)-4-hydroxy-4-(2'-methoxy-6'-methyl-3'-(prop-2-yl)-cyclohex-1-enyl)-2-methyl-3-(tert-butoxy)-cyclobut-2-enone 
• 89-80-5 p-menthan-2-one 
• 59781-56-5 1--1-ethanon 
• 68298-49-7 (3-Methyl-6-(1-methylethyl)-1-cyclohexen-1-yl)acetat 
• 59781-47-4 r-2-Acetyl-t-3-methyl-c-6-(1-methylethyl)-1-cyclohexanon 
• 946524-55-6 t-3-Methyl-c-6-(1-methylethyl)-r-2-(2-propenyl)-1-cyclohexanon 
• 105252-10-6 c-3-Methyl-c-6-(1-methylethyl)-r-2-(2-propenyl)-1-cyclohexanon 
• 105367-46-2 ((3S,6S)-6-Isopropyl-3-methyl-cyclohex-1-enyloxy)-trimethyl-silane 
• 105252-07-1 r-2,t-3-Dimethyl-c-6-(1-methylethyl)-1-cyclohexanon 
• 105252-08-2 r-2,c-3-Dimethyl-c-6-(1-methylethyl)-1-cyclohexanon 
• 4573-50-6 (S)-(+)-piperitone 

Relevant academic research and scientific papers

Synthesis of ent-nanolobatolide

Efficient and adaptable: The key steps in the total synthesis of ent-nanolobatolide, the enantiomer of the novel and potent neuroprotective agent, involve an oxidative ring expansion of (-)-menthone, a Nazarov cyclization, an intermolecular Diels-Alder re

Thermally induced cyclobutenone rearrangements and domino reactions

(Chemical Equation Presented) Four thermal-rearrangement pathways and a domino reaction leading to quinones arise from the thermolysis of cyclobutenones. The course of vinylcyclobutenone rearrangements is dictated by the nature of the substituent, R (see

Enantioselective acetalization of racemic 1,3-alkanediols with l-methone under kinetically controlled conditions

Racemic 1,3-alkanediols (rac-1) undergo an enantioselective acetalization by treatment with l-methone enol trimethylsilyl ether (10) in the presence of trifluoromethanesulfonic acid (10 mol%) to give thermodynamically less stable spiroacetal 3 (derived fr

Intramolecular Diels-Alder Approach to Cadinane and Amorphane Sesquiterpenes

A synthetic route to both cadinane and amorphane type sesquiterpenes is described.Successful implementation of this route showed the structures previously considered for cadinenal (1) and dehydrocadinenal (2) to be incorrect, but confirmed both the relative and absolute configurations proposed for pernetic acid C (3) and pernetic acid B (4).

Structure-Odor Correlation, V. - From Menthone to Shyobunone - Change of Odor with Structure

Derivatives of menthone (4) were prepared by substitution at C-2 or C-3 whereby increasing similarity with the shyobunones (1, 2) should be achieved.Thus, the 3,3-disubstituted ketones 5-11 were synthesized by 1,4-addition to piperitone(3).The ketones 18 and 19 substituted at C-2 were prepared via the silyl ether 15.Analogously the ketones 22-25 have been synthesized.The ketones 28 and 29 were obtained from 15 via the diketone 20 and the aldol 21. - Key compound for the synthesis of 43 and 44 as well as 1 and 2 by 1,4-addition was the known ketone 40.While preparing 40 the side products 41 and 42 have also been obtained.The olfactory properties of the substituted menthones change stepwise from the minty odor of 4 by addition of spicy and woody notes up to those of 1 and 2 which possess a fruity-earthy-woody odor.

Sensitized Photooxygenation of Silyl Enol Ethers of Cyclic Ketones

α,β-Unsaturated and α-hydroxy ketones are accessible in prototropic ene-reactions with singlet oxygen by sensitized photooxygenation of cyclic silyl enol ethers and subsequent reduction and solvolysis.In a competing silatropic ene-reaction α-silyloxyketones are formed.Formation of different products depends on ring size, configuration and substitution.At C-6 chirally substituted 2-cyclohexenones are synthesized for the first time by sensitized photooxygenation of chiral silyl enol ethers of optically active starting ketones.