13487-30-4

Usage

Uses

Used in Perfume and Cosmetic Industry:
2,6,6-Trimethylcyclohexa-2,4-dienone is used as a fragrance ingredient for its sweet and floral aroma, enhancing the scent profiles of perfumes and cosmetics.
Used in Flavor Production:
2,6,6-trimethylcyclohexa-2,4-dienone is utilized in the production of flavors, contributing to the development of unique taste experiences in food and beverage products.
Used as a Chemical Intermediate:
2,6,6-Trimethylcyclohexa-2,4-dienone serves as a chemical intermediate in the synthesis of other compounds, playing a crucial role in the creation of various chemical products.
Used in Organic Synthesis and Pharmaceutical Research:
Due to its chemical structure and properties, 2,6,6-trimethylcyclohexa-2,4-dienone has been studied for its potential application in organic synthesis and pharmaceutical research, indicating its versatility in scientific fields.

InChI:InChI=1/C9H12O/c1-7-5-4-6-9(2,3)8(7)10/h4-6H,1-3H3

Upstream product

• 74768-99-3 2,6,6-Trimethyl-4-(phenylselenyl)-2-cyclohexen-1-on 
• 85219-18-7 2,6,6-trimethyl-5-pyrrolidino-cyclohex-2-enone 
• 576-26-1 2.6-dimethylphenol 
• 74-88-4 methyl iodide 
• 59822-10-5 (+/-)-5-bromo-3-methyl-1-pentene 
• 1125-21-9 2,6,6-trimethyl-2-cyclohexene-1,4-dione 
• 107536-93-6 (+/-)-4-acetoxy-2,6,6-trimethyl-2-cyclohexenone 
• 74768-98-2 4-bromo-2,6,6-trimethyl-2-cyclohexen-1-one 
• 19620-37-2 (+/-)-4-hydroxy-2,6,6-trimethyl-2-cyclohexenone 
• 526-73-8 1,2,3-trimethylbenzene 

Downstream Products

• 100084-46-6 1,11,11-Trimethyl-4-phenyl-2,4,6-triazatricyclo<5.2.2.0^2,6>undec-8-en-3,5,10-trion 
• 54702-01-1 (S)-2,6,6-Trimethyl-1-(3-methyl-pent-4-enyl)-cyclohexa-2,4-dienol 
• 69903-52-2 1-[3-oxo-pent-4-en-1-yl]-1-trimethylsilyloxy-2,6,6-trimethylcyclohexa-2,4-diene 
• 17806-54-1 (4aR,6S,8aR)-4,8a,9,9-Tetramethyl-4a,5,6,7,8,8a-hexahydro-2H-1,6-methano-naphthalen-1-ol 
• 5986-55-0 (+/-) patchoulol 
• 75253-61-1 5-(1-Hydroxy-2,6,6-trimethylcyclohexa-2,4-dienyl)-1-penten-3-one 
• 75253-62-2 5-(2,3,6-trimethylphenyl)-1-penten-3-one 
• 59700-21-9 methyl-3 (trimethyl-2,3,6 phenyl)-5 pentene-1 ol-3 
• 79862-13-8 2,3,6-trimethyl-1-(3-methyl-4-penten-1-yl)benzene 

Relevant academic research and scientific papers

A New Access to 2,6,6-Trimethylcyclohexa-2,4-dienone from 4-Oxoisophorone

2,6,6-Trimethylcyclohexa-2,4-dienone (1), a versatile starting material for the preparation of some carotenoids and several natural products, was efficiently (73 percent yield) prepared from oxoisophorone 3.After conversion of 3 to the alcohol 4 or the acetate 5, H2O was eliminated (4 -> 1) under acidic distillative conditions, whereas AcOH could be eliminated (5 -> 1) under Pd(O) catalysis.

Photochemical Reactions. 135th Communication. Photochemistry of Homoconjugated Cyclobutanones. II. Decisive Effect of gem-Dimethyl Substitution on the Course of the Oxa-di-?-methane Rearrangement

The synthesis and photolysis of the spirocyclobutanones 4-7 incorporating a cyclohexa-, cyclohepta- and cyclooctadiene moiety, respectively, is described.On triplet excitation, these compounds undergo isomerisation via a 1,2-acyl shift involving one or both double bonds of the diene system.The presence of a gem-dimethyl group as in 1, 4 and 7 dramatically changes the photoproduct distribution, since only these substrates lead to the products 3, 29 and 34 resulting from vinylogous ring closure (Scheme 5).Those substrates without methyl substitution (5 and 6) give only products of a rearrangement involving one double bond.

Addition of Vinylketenes to Enamines. A Method for the Preparation of 6,6-Dialkylcyclohexa-2,4-dienones and 4,4-Dialkyl-2-vinylcyclobutenones

Drei Enamine (1-3) wurden mit fuenf Vinylketenen (5a-5e) (s.Schema 2) zur Reaktion gebracht.Die Vinylketene wurde in situ durch HCl-Eliminierung aus α,β-ungesaettigten Saeurechloriden mit Triaethylamin hergestellt.Die Cycloadditionen von 1-3 an 5a-5e fuehrten zu 6,6-Dialkyl-5-dialkylaminocycohex-2-enonen (kurz: Cyclohexenone) bzw. zu 3-Dialkylamino-4,4-dimethyl-2-vinylcyclobutanonen (kurz: Vinylcyclobutanone) oder zu einem Gemisch der beiden, je nach Natur der Partner bzw. des Loesungsmittels (s.Tab. 1).Durch oxidative Amin-Eliminierung wurden die Cyclohexenone in 6,6-Dialkylcyclohexa-2,4-dienone und die Vinylcyclobutanone in 4,4-Dialkyl-2-vinylcyclobutenone uebergefuehrt.Diese Reaktion stellt eine einfache Synthese von verschieden substituierten 6,6-Dialkylcyclohexa-2,4-dienonen bzw. 4,4-Dialkyl-2-vinylcyclobutenonen (siehe Schema 1) dar.

A Stereocontrolled Access to (+/-)-, (-)-, and (+)-Patchouli Alcohol

The racemate and both enantiomers of patchouli alcohol have been synthesized by stereocontrolled routes.The olfactive properties of the alcohols prepared are reported.

Light-induced Reactions, XIV. Rules for Determining Spectra of 2,4-Cyclohexadien-1-ones

2,4-Cyclohexadien-1-ones of formula types 1 to 5 (cf.Fig. 1) provide basic values and positional increments for UV and 13C NMR spectra.These parameters allow to distinguish between constitutional isomers belonging to one and the same column of the graph of Fig. 1.It has become possible, e.g., to identify clearly the constitutional isomers 6 and 8 or 12 and 14, respectively.

SUR UNE SOLUTION DE RECHANGE A LA CYCLISATION DES ε-HALOGENOCETONES - APPLICATION A LA SYNTHESE DU (+/-) PATCHOULOL.

A short synthesis of (+/-) patchoulol is described in wich the cyclisation of the methoxymethylether from a δ-ethylenic γ-hydroxyketone constitutes the key step.

Tricyclic alcohols

Tricyclic alcohol compounds having the formula: STR1 wherein each of R1, R2, R3, R4, R5 and R6 is selected from the group consisting of hydrogen and methyl; wherein the dashed line is a carbon-carbon single bond or a carbon-carbon double bond; and wherein, when the dashed line is a carbon-carbon single bond, one of R2 or R3 is hydrogen; useful in preparing compositions for augmenting or enhancing the flavor and/or aroma of consumble products including foods, tobacco and perfumes.

Process for the preparation of sesquiterpenic derivatives

Process for the preparation of tricyclic sesquiterpenes which comprises reacting a cyclohexadienic carbinol with a strongly basic agent. The products obtained in accordance with the process of the invention are useful ingredients in the perfumery. Some of the said products are new.