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 
• 38313-10-9 (+/-)-6,6-dimethylcyclohex-2-en-1-ol 
• 73741-66-9 6,6-Dimethyl-1-methoxy-1-cyclohexen 
• 930-68-7 cyclohexenone 
• 74-88-4 methyl iodide 
• 62952-32-3 3-ethoxy-6,6-dimethylcyclohex-2-en-1-one 
• 6610-21-5 6-methylcyclohex-2-en-1-one 
• 91056-64-3 6,6-dimethylcyclohex-1-enyl acetate 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 115-11-7 isobutene 
• 1073-13-8 4,4-dimethylcyclohexenone 

Downstream Products

• 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 
• 144225-48-9 2,2-dimethyl-3-(2-propenyl)cyclohexanone 
• 29410-73-9 6,6-Dimethyl-2-(2-oxo-propyl)-cyclohex-2-enone 
• 444809-15-8 1-methoxymethoxymethyl-6,6-dimethyl-cyclohex-2-enol 
• 144225-50-3 2,2-Dimethyl-butyric acid (1S,6R)-6-allyl-3,3-dimethyl-2-oxo-cyclohexylmethyl ester 
• 1429645-58-8 5-(4-methoxyphenyl)-2,2-dimethylcyclohexanone 
• 1429645-59-9 3-(4-methoxyphenyl)-6,6-dimethylcyclohex-2-enone 
• 1629798-35-1 (E)-N-(6,6-dimethylcyclohex-2-en-1-ylidene)-4-methylbenzenesulfonamide 

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.

Ruthenium Lewis Acid-Catalyzed Asymmetric Diels–Alder Reactions: Reverse-Face Selectivity for α,β-Unsaturated Aldehydes and Ketones

Acrolein, methacrolein, methyl vinyl ketone, ethyl vinyl ketone, 3-methyl-3-en-2-one, and divinyl ketone were coordinated to a cationic cyclopentadienyl ruthenium(II) Lewis acid incorporating the electron-poor bidentate BIPHOP–F ligand. Analysis by NOESY and ROESY NMR techniques allowed the determination of conformations of enals and enones present in solution in CD2Cl2. The results were compared to solid-state structures and to the facial selectivities of catalytic asymmetric Diels–Alder reactions with cyclopentadiene. X-Ray structures of four Ru-enal and Ru-enone complexes show the α,β-unsaturated C=O compounds to adopt an anti-s-trans conformation. In solution, enals assume both anti-s-trans and anti-s-cis conformations. An additional conformation, syn-s-trans, is present in enone complexes. Enantioface selectivity in the cycloaddition reactions differs for enals and enones. Reaction products indicate enals to react exclusively in the anti-s-trans conformation, whereas with enones, the major product results from the syn-s-trans conformation. The alkene in s-cis conformations, while present in solution, is shielded and cannot undergo cycloaddition. A syn-s-trans conformation is found in the solid state of the bulky 6,6-dimethyl cyclohexanone-Ru(II) complex. The X-ray structure of divinyl ketone is unique in that the Ru(II) center binds the enone via a η2bond to one of the alkene moieties. In solution, coordination to Ru–C=O oxygen is adopted. A comparison of facial preference is also made to the corresponding indenyl Lewis acids.