23438-77-9

Basic information

• Product Name: 3,6,6-Trimethyl-2-cyclohexen-1-one
• Synonyms: 3,6,6-Trimethyl-2-cyclohexen-1-one;α,β-Pulenenone
• CAS NO: 23438-77-9
• Molecular Formula: C₉H₁₄O
• Molecular Weight: 138.2069
• Mol File: 23438-77-9.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 208°C (estimate)
• Flash Point: 75.7°C
• Appearance: /
• Density: 0.9270
• Vapor Pressure: 0.389mmHg at 25°C
• Refractive Index: 1.4798 (estimate)
• CAS DataBase Reference: 3,6,6-Trimethyl-2-cyclohexen-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6,6-Trimethyl-2-cyclohexen-1-one(23438-77-9)
• EPA Substance Registry System: 3,6,6-Trimethyl-2-cyclohexen-1-one(23438-77-9)

Safety Data

• Hazardous Substances Data: 23438-77-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H14O/c1-7-4-5-9(2,3)8(10)6-7/h6H,4-5H2,1-3H3

Upstream product

• 32937-45-4 6-dichloromethyl-3,6-dimethyl-cyclohex-2-enone 
• 289046-36-2 2,2,5-trimethyl-cyclohex-3-enone 
• 1073-13-8 4,4-dimethylcyclohexenone 
• 917-54-4 methyllithium 
• 563-80-4 3-methyl-butan-2-one 
• 78-94-4 methyl vinyl ketone 
• 81360-62-5 trans-6-tert-butyl-3-hydroxy-2-methyl-1-(trimethylsiloxy)-1-cyclohexene 
• 163068-87-9 2-methyl-2-(3,3-dimethyl-4-oxopentyl)-1,3-dioxolane 
• 78-82-0 Isobutyronitrile 
• 78-79-5 isoprene 
• 20989-95-1 3,3-Dimethyl-1-isopropyliden-cyclobutanon-⁽²⁾ 
• 22635-75-2 2,2,3,3-Tetramethyl-4-methylen-cyclobutanon 
• 188620-91-9 phenyl 3-(2,2-dimethylcyclopropyl)but-2(E)-enyl selenoate 
• 233664-96-5 2-(trimethylsilyloxy)-3,3-dimethyl-1-hepten-5-yne 

Downstream Products

• 933-36-8 2,2,5-trimethylcyclohexanone 
• 73210-25-0 2,2,5-Trimethyl-cyclohexanol 
• 38693-71-9 3,6,6-Trimethylcyclohex-2-enthion 
• 95-87-4 2,5-Dimethylphenol 
• 106-42-3 para-xylene 
• 2416-94-6 2,3,6-trimethylphenol 
• 108-68-9 3,5-Dimethylphenol 
• 144528-01-8 2,5,5-trimethyl-5-(2-propenyl)-cyclohexanone 
• 91763-40-5 1,1,4-Trimethyl-3-allyl-cyclohexen-⁽³⁾-on-⁽²⁾ 
• 80007-04-1 3,6,6-trimethyl-1-cyclohexenecarboxaldehyde 
• 80007-03-0 C₁₆H₂₄N₂O₂S 

Relevant articles and documents

The first addition of silyl enol ethers to internal unactivated alkynes

The EtAlCl2-mediated intramolecular addition of silyl enol ethers to both terminal and internal unactivated alkynes, bearing alkyl and phenyl susbstituents at the alkyne moiety, proceeded exclusively in the endo- fashion to give mono- and bicyc

Ketone Formation from Carboxylic Acids by Ketonic Decarboxylation: The Exceptional Case of the Tertiary Carboxylic Acids

For the reaction mechanism of the ketonic decarboxylation of two carboxylic acids, a β-keto acid is favored as key intermediate in many experimental and theoretical studies. Hydrogen atoms in the α-position are an indispensable requirement for the substrates to react by following this mechanism. However, isolated observations with tertiary carboxylic acids are not consistent with it and these are revisited and discussed herein. The experimental results obtained with pivalic acid indicate that the ketonic decarboxylation does not occur with this substrate. Instead, it is consumed in alternative reactions such as disintegration into isobutene, carbon monoxide, and water (retro-Koch reaction). In addition, the carboxylic acid is isomerized or loses carbon atoms, which converts the tertiary carboxylic acid into carboxylic acids bearing α-proton atoms. Hence, the latter are suitable to react through the β-keto acid pathway. A second substrate, 2,2,5,5-tetramethyladipic acid, reacted by following the same retro-Koch pathway. The primary product was the monocarboxylic acid 2,2,5-trimethyl-4-hexenoic acid (and its double bond isomer), which might be further transformed into a cyclic enone or a lactone. The ketonic decarboxylation product, 2,2,5,5-tetramethylcyclopentanone was observed in traces (0.2 % yield). Therefore, it can be concluded that the observed experimental results further support the proposed mechanism for the ketonic decarboxylation via the β-keto acid intermediate.

OPSIN-BINDING LIGANDS, COMPOSITIONS AND METHODS OF USE

Compounds are disclosed that are useful for treating ophthalmic conditions caused by or related to production of toxic visual cycle products that accumulate in the eye, such as dry adult macular degeneration, as well as conditions caused by or related to the misfolding of mutant opsin proteins and/or the mis-localization of opsin proteins. Compositions of these compounds alone or in combination with other therapeutic agents are also described, along with therapeutic methods of using such compounds and/or compositions. Methods of synthesizing such agents are also disclosed.