20013-73-4

Basic information

• Product Name: 2,6,6-trimethylcyclohex-2-en-1-one
• Synonyms: 2,6,6-trimethylcyclohex-2-en-1-one;2-Cyclohexen-1-one, 2,6,6-trimethyl-;2,6,6-Trimethyl-2-cyclohexen-1-one;Einecs 243-465-7
• CAS NO: 20013-73-4
• Molecular Formula: C₉H₁₄O
• Molecular Weight: 138.20686
• EINECS: 243-465-7
• Mol File: 20013-73-4.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 196.9°Cat760mmHg
• Flash Point: 75.7°C
• Appearance: /
• Density: 0.905g/cm³
• Vapor Pressure: 0.389mmHg at 25°C
• Refractive Index: 1.455
• CAS DataBase Reference: 2,6,6-trimethylcyclohex-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6,6-trimethylcyclohex-2-en-1-one(20013-73-4)
• EPA Substance Registry System: 2,6,6-trimethylcyclohex-2-en-1-one(20013-73-4)

Safety Data

• Hazardous Substances Data: 20013-73-4(Hazardous Substances Data)

Usage

Uses

2,6,6-Trimethyl-2-cyclohexen-1-one is a derivative of Cyclohexanone (C987980), an intermediate in the synthesis of CCNU, an effective antitumor agent.

InChI:InChI=1/C9H14O/c1-7-5-4-6-9(2,3)8(7)10/h5H,4,6H2,1-3H3

Upstream product

• 565-69-5 ethyl isopropyl ketone 
• 107-02-8 acrolein 
• 2408-37-9 2,2,6-trimethylcyclohexan-1-one 
• 61875-95-4 6-acetoxy-5,5-dimethyl-2-cyclohexen-1-one 
• 4694-17-1 5,5-dimethlycyclohex-2-en-1-one 
• 83999-44-4 2,6,6-trimethyl-1-trimethylsilyloxycyclohexene 
• 35122-36-2 (E)-2,6,6-Trimethyl-α-(1-propenyl)-1-cyclohexene-1-methanol 
• 40790-56-5 2,6-dimethyl-2-cyclohexen-1-one 
• 74-88-4 methyl iodide 
• 113832-58-9 (E)-1-<2-(Cyclohexylimino)ethyl>-2,6,6-trimethyl-2-cyclohexen-1-ol 
• 91413-25-1 (1-Isopropylidene-2-methyl-pent-4-enyloxy)-methyl-diphenyl-silane 
• 3375-31-3 palladium diacetate 
• 60775-85-1 2-ethyl-2-methoxy-3,3-dimethyl-3,4-dihydro-2H-pyran 
• 13155-73-2 2-chloro-2,6,6-trimethylcyclohexanone 

Downstream Products

• 113857-71-9 (Z)-1-(3-Methoxy-2-propen-1-yl)-2,6,6-trimethyl-2-cyclohexen-1-ol 
• 113831-74-6 1-(3-Hydroxy-1-propinyl)-2,6,6-trimethyl-2-cyclohexen-1-ol 
• 113832-66-9 4-(1-Hydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-3-oxobutansaeure-methylester 
• 41641-11-6 2,6,6-trimethyl-1-hydroxy-1-[3-hydroxy-but-1-ynyl]-cyclohex-2-ene 
• 60814-36-0 1-ethoxyethynyl-2,6,6-trimethyl-cyclohex-2-enol 
• 10130-91-3 cis-2,2,6-trimethylcyclohexanol 
• 10130-91-3 (+/-)-2,2,6t-trimethyl-cyclohexan-r-ol 
• 87887-12-5 1-(cis-2,2,6-Trimethylcyclohexyloxy)-2-pentanol 
• 87887-12-5 1-(trans-2,2,6-Trimethylcyclohexyloxy)-2-pentanol 
• 50-00-0 formaldehyd 
• 23726-91-2 beta damascone 
• 1390627-51-6 (E)-3-(3-(1-hydroxy-2,6,6-trimethylcyclohex-2-enyl)propylidene)-dihydrofuran-2(3H)-one 
• 10130-91-3 2,2,6-trimethyl-cyclohexanol 
• 78831-69-3 2,6,6-trimethyl-cyclohex-3-en-1-one 

Relevant articles and documents

DEHYDROGENATION REACTION

The present invention relates to the field of organic synthesis and more specifically it concerns a process for the dehydrogenation of compound of formula (I) catalyzed by palladium (Pd0) in elemental metallic form.

A brief and stereoselective synthesis of limonoid models, with antifeedant activity against Locusts migratoria

A short stereoselective preparation of havanensin-type limonoid models is reported. The synthesis is based on a radical domino reaction of an epoxyketone to a bicyclic hydroxyketone, and is achieved in six and nine steps from simple cyclohexenones. The epoxyhavanensin derivatives show significant antifeedant activity against Spodoptera littoralis and Spodoptera frugiperda, and the epoxyketone 21 shows potent antifeedant activity against Locusts migratoria.

Structure-Odor Correlation, VII. - Synthesis and Olfactive Properties of Theaspirane Analogues

The spirodihydrofurans 8-12 were prepared by addition of the respective alkynols to the ketone 20 (-->21-25), Lindlar hydrogenation (-->26-30), and cyclization. - The saturated derivatives 1-6 were available either by hydrogenation (8-10-->1,2,4) or via the lactol 47 and its reaction to the diols 31-36.Addition of the ethyl acetate anion to 20 (-->71), reduction (71-->73), and cyclization yielded the spirooxetane 13. - From the ynediols 76 and 77, Lindlar hydrogenation (-->78,79), cyclization (-->80,81), and further hydrogenation led to the spirotetrahydropyranes 16and 17. - Key compound for the synthesis of the ketone 18 was the geranic acid derivative 94, which could be obtained in two different ways.Cyclization of 94 to the diester 92 and Dieckmann condensation of 92 under simultaneous methylation (-->99) led to 18.The diastereoisomers 18a and b could be assigned after reduction of 18 to the separable alcohols 19a-c. - The olfactive properties (strength and quality) of the theaspirane analogues are determined by the conformational flexibility of the respective molecule.Thus, the almost rigid 13 has a very strong camphoraceous-herbaceous odor.Augmenting flexibility, particularly by increasing of the ring size (-->1,-->16), but also by alkyl substitution at C-2, results in remarkably weaker, woody-flowery notes.