6553-64-6

Basic information

• Product Name: 6,6-dimethylcyclohex-2-en-1-one
• Synonyms: 2-cyclohexen-1-one, 6,6-dimethyl-; 6,6-Dimethylcyclohex-2-en-1-one
• CAS NO: 6553-64-6
• Molecular Formula: C₈H₁₂O
• Molecular Weight: 124.1803
• EINECS: 613-816-2
• Mol File: 6553-64-6.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 179.815°C at 760 mmHg
• Flash Point: 64.883°C
• Density: 0.922g/cm³
• Vapor Pressure: 0.924mmHg at 25°C
• Refractive Index: 1.458
• CAS DataBase Reference: 6,6-dimethylcyclohex-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6,6-dimethylcyclohex-2-en-1-one(6553-64-6)
• EPA Substance Registry System: 6,6-dimethylcyclohex-2-en-1-one(6553-64-6)

Safety Data

• Hazardous Substances Data: 6553-64-6(Hazardous Substances Data)

Upstream product

• 108-75-8 2,4,6-trimethyl-pyridine 
• 21690-26-6 6-bromo-2,2-dimethylcyclohexan-1-one 
• 563-80-4 3-methyl-butan-2-one 
• 107-02-8 acrolein 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 115-11-7 isobutene 
• 38313-10-9 (+/-)-6,6-dimethylcyclohex-2-en-1-ol 
• 73741-66-9 6,6-Dimethyl-1-methoxy-1-cyclohexen 
• 91056-64-3 6,6-dimethylcyclohex-1-enyl acetate 
• 3375-31-3 palladium diacetate 
• 99165-64-7 (1-Isopropylidene-pent-4-enyloxy)-methyl-diphenyl-silane 
• 38309-48-7 6,6-dimethyl-trans-2,3-epoxycyclohexanol 
• 930-68-7 cyclohexenone 
• 74-88-4 methyl iodide 

Downstream Products

• 18329-25-4 5-isopropyl-2,2-dimethylcyclohexan-1-one 
• 55337-84-3 4-bromo-6,6-dimethyl-cyclohex-2-enone 
• 99342-65-1 6,6-dimethyl-cyclohex-2-enone-(2,4-dinitro-phenylhydrazone) 
• 151408-92-3 2,2-dimethyl-5-<2-(1,3-dioxa-2-cyclohexyl)ethyl>cyclohexan-1-one 
• 144225-48-9 2,2-dimethyl-3-(2-propenyl)cyclohexanone 
• 73982-30-6 6,6-dimethyl-2,3-epoxycyclohexan-1-one 
• 73982-31-7 2-(3'-oxo-6',6'-dimethylcyclohexyl)-6,6-dimethylcyclohex-2-en-1-one 
• 1193-47-1 2,2-dimethyl-cyclohexanone 
• 38313-10-9 (+/-)-6,6-dimethylcyclohex-2-en-1-ol 
• 157952-83-5 2-iodo-6,6-dimethylcyclohex-2-en-1-one 
• 76440-46-5 3-((p-tert-butylphenyl)thio)-6,6-dimethylcyclohexanone 
• 81435-32-7 (4,4-Dimethyl-3-trimethylsilanyloxy-cyclohex-2-enyl)-phosphonic acid diethyl ester 
• 29410-73-9 6,6-Dimethyl-2-(2-oxo-propyl)-cyclohex-2-enone 
• 29410-72-8 2-(5,5-Dimethyl-6-oxo-cyclohex-1-enyl)-2-methyl-propionaldehyde 

Relevant articles and documents

Reactions of Singlet Oxygen with Enol Esters

Singlet oxygenation of 1-adamantylideneethyl acetate (4) and 6,6-dimethylcyclohex-1-enyl acetate (7) produces only "ene" reaction products.Photooxygenation of Δ1,6-2-oxabicyclodecen-3-one (9), in contrast, yields ene, acyl-shifted, and cycloaddition products.The product distribution resulting from oxidation of 9 indicates that attack of singlet oxygen (1O2) occurs exclusively on the same side of the double bond as the ester functional group.The bimolecular rate constant for reaction of 9 with 1O2 is found to be ca. 50 times larger than those of 4 and 7.These results are explained most economicaly by invoking the ini tial formation of a perepoxide intermediate.In the case of 9, stabilization of the transition state leading to the perepoxide by interaction of the incoming 1O2 molecule with the ester functionally produces the observed rate enhancement and stereospecificity.

Tuning of α-Silyl Carbocation Reactivity into Enone Transposition: Application to the Synthesis of Peribysin D, E-Volkendousin, and E-Guggulsterone

A reliable method for enone transposition has been developed with the help of silyl group masking. Enantio-switching, substituent shuffling, and Z-selectivity are the highlights of the method. The developed method was applied for the first total synthesis of peribysin D along with its structural revision. Formal synthesis of E-guggulsterone and E-volkendousin was also claimed using a short sequence.

11-Step Total Synthesis of (-)-Maoecrystal v

An expedient, practical, and enantioselective route to the highly congested ent-kaurane diterpene maoecrystal V is presented. This route, which has been several years in the making, is loosely modeled after a key pinacol shift in the proposed biosynthesis. Only 11 steps, many of which are strategic in that they build key skeletal bonds and incorporate critical functionalities, are required to access (-)-maoecrystal V. Several unique and unexpected maneuvers are featured in this potentially scalable pathway. Reevaluation of the biological activity calls into question the initial exuberance surrounding this natural product.