25576-25-4

Basic information

• Product Name: 1,3,3-TriMethyl-2-[(1E,3E)-3-Methyl-1,3-hexadien-5-ynyl]-cyclohexane
• Synonyms: 1,3,3-TriMethyl-2-[(1E,3E)-3-Methyl-1,3-hexadien-5-ynyl]-cyclohexane;(E,E)-1,3,3-TriMethyl-2-(3-Methyl-1,3-hexadien-5-ynyl)cyclohexene;(E,E)-3-Methyl-1-(2,6,6-triMethyl-1-cyclohexen-1-yl)-1,3-hexadien-5-yne
• CAS NO: 25576-25-4
• Molecular Formula: C₁₆H₂₂
• Molecular Weight: 216
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Retinoids
• Mol File: 25576-25-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 299.2±9.0 °C(Predicted)
• Appearance: /
• Density: 0.919±0.06 g/cm3(Predicted)
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate, Hexane
• CAS DataBase Reference: 1,3,3-TriMethyl-2-[(1E,3E)-3-Methyl-1,3-hexadien-5-ynyl]-cyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,3-TriMethyl-2-[(1E,3E)-3-Methyl-1,3-hexadien-5-ynyl]-cyclohexane(25576-25-4)
• EPA Substance Registry System: 1,3,3-TriMethyl-2-[(1E,3E)-3-Methyl-1,3-hexadien-5-ynyl]-cyclohexane(25576-25-4)

Safety Data

• Hazardous Substances Data: 25576-25-4(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Oil

Uses

Intermediate in the preparation of Retinoic Acid derivatives.

Upstream product

• 17974-55-9 (2E,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate 
• 22029-76-1 beta-ionol 
• 303779-99-9 (E)-2-(2,6,6-trimethylcyclohexen-1-yl)-ethenyl (trifluoromethyl)sulfonate 
• 3917-41-7 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal 
• 37384-77-3 ethyl β-ionylidene acetate 
• 3917-39-3 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexenyl)-2,4-pentadien-1-ol 
• 79-77-6 (E)-β-ionone 
• 884845-78-7 N-benzyl-N-methoxy-3-(2,6,6-trimethyl-cyclohex-1-enyl)-acrylamide 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 74352-12-8 9-(2-propynyl)-β-ionyl acetate 
• 917-54-4 methyllithium 
• 79985-69-6 (2E,4E,6E)-2-Fluoro-5-methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trienoic acid 
• 624-67-9 Propargylic aldehyde 
• 66556-69-2 (E)-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1-buten-3-yltriphenylphosphonium bromide 

Downstream Products

• 210700-51-9 ((2E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,6,8-trien-4-ynyloxy)(tert-butyl)dimethylsilane 
• 885050-34-0 [9,10-13C₂]-11Z-retinol 
• 29443-88-7 (2E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6,8-trien-4-yn-1-ol 
• 68-26-8 vitamine A 
• 22737-96-8 11-cis-retinol 
• 68-26-8 RETINOL 
• 2130-30-5 1,18-Bis-<2,2,6-trimethyl-cyclohexen-(6)-yl>-7,12-dihydroxy-3,7,12,16-tetramethyl-octadeca-heptaen-(1,3,5,9,13,15,17) 
• 302-79-4 all-trans-retinoic-acid 
• 353744-05-5 ethyl (2E,4E,6E,8E)-7-methyl-3-(2-phenyl)ethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate 
• 353744-02-2 ethyl (2E,4E,6E,8E)-7-methyl-3-propyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate 
• 353744-01-1 ethyl (2E,4E,6E,8E)-3-ethyl-7-methyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate 
• 353744-04-4 ethyl (2E,4E,6E,8E)-3-butyl-7-methyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate 
• 3899-20-5 ethyl (all-E)-retinoate 
• 59699-82-0 ethyl 13-cis-retinoate 

Relevant articles and documents

Carboxylate-directed tandem functionalisations of α,β- dihaloalkenoic acids with 1-alkynes: A straightforward access to (Z)-configured, α,β-substituted γ-alkylidenebutenolides

An easy and mild copper(I)-catalysed lactonisation of readily available (E)-2,3-dihalopropenoic acid derivatives regio- and stereoselectively leads to rarely described (Z)-3-halo-5-ylidene-5H-furan-2-ones. These compounds are subsequently able to undergo classical Pd-catalysed cross-coupling reactions, providing 3-substituted and 3,4-disubstituted 5-ylidene-5H-furan-2-ones (see scheme).

Accurate measurements of 13C-13C J-couplings in the rhodopsin chromophore by double-quantum solid-state NMR spectroscopy

A new double-quantum solid-state NMR pulse sequence is presented and used to measure one-bond 13C-13C J-couplings in a set of 13C2-labeled rhodopsin isotopomers. The measured J-couplings reveal a perturbation of the electronic structure at the terminus of the conjugated chain but show no evidence for protein-induced electronic perturbation near the C11-C12 isomerization site. This work establishes NMR methodology for measuring accurate 1JCC values in noncrystalline macromolecules and shows that the measured J-couplings may reveal local electronic perturbations of mechanistic significance. Copyright

Stereocontrolled synthesis of 13-substituted retinoic acids by palladium-catalyzed coupling reaction of alkenyl stannane with vinyl triflate

A novel method for the stereoselective synthesis of all-E-, 13Z- and 9Z- retionic acid esters was developed by palladium-catalyzed cross coupling reactions of tetraenyl stannanes with E- or Z-vinyl triflates in good yields. Applying this methodology, 13-substituted all-E- and 9Z- retinoic acids were prepared in satisfactory yields.