73395-75-2

Usage

Chemical Properties

Oil

InChI:InChI=1/C13H18/c1-5-6-9-12-11(2)8-7-10-13(12,3)4/h1,6,9H,7-8,10H2,2-4H3/b9-6+

Upstream product

• 79-77-6 (E)-β-ionone 

Downstream Products

• 101315-24-6 8-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-7-octen-3,5-diin-2-ol 
• 96617-90-2 (7E,12Z)-12,20-tetramethylene-9,10-didehydro-11,14-dihydro-9-demethyl-11-hydroxyretinyl tert-butyldimethylsilyl ether 
• 106140-56-1 methyl 5-(2,6,6-trimethylcyclohexen-1-yl)-4-penten-2-ynoate 
• 138846-06-7 2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene 
• 22255-47-6 (E)-2-(3-methylbuta-1,3-dienyl)-1,3,3-trimethyl-cyclohex-1-ene 
• 74311-19-6 (13Z)-13-Desmethylretinal 
• 472-86-6 13-cis-vitamin A aldehyde 
• 173214-57-8 (E)-5-(2,6,6-trimethylcyclohexen-1-yl)pent-4-en-2-ynenitrile 
• 5358-27-0 all-trans-9-Desmethyl-vitamin-A-saeure 
• 100991-97-7 ethyl (13E)-20,20,20-trifluororetinoate 
• 256518-34-0 pinacol [(1E,3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)buta-1,3-dienyl]borane 
• 62170-41-6 (E)-trimethyl(pent-3-en-1-yn-1-yl)silane 
• 51468-89-4 1,3,3-trimethyl-2-[(1E,3E)-3-methyl-1,3-pentadienyl]cyclohexene 
• 25340-80-1 1,8-bis(trimethylsilyl)octa-3,5-diene-1,7-diyne 

Relevant academic research and scientific papers

Stereoselective synthesis of trienoic acids: Synthesis of retinoic acids and analogues

Stereoselective construction of conjugated trienoic acids was achieved through two successive Stille reactions, the first step consisting of the coupling of (E)-1,2-bis(tributylstannyl)ethene and tributylstannyl (Z)- or (E)-3-iodoalk-2-enoates. Two different routes were used for the second step: (1) cross-coupling of the stannyldienoic acid reagents and vinyl iodides, or (2) cross-coupling of vinylstannane reagents and the tributylstannyl 5-iodopenta-2,4-dienoates generated by iododestannylation of stannyldienes. Vinylstannanes synthesized by stannylmetalation of the Negishi dienyne derived from β- or α-ionone and safranal thus provided access to stereodefined retinoic acids. Some retinoid and yne analogues were also prepared by Sonogashira coupling. Georg Thieme Verlag Stuttgart.

A novel, selective, and efficient route to carotenoids and related natural products via Zr-catalyzed carboalumination and Pd- and Zn-catalyzed cross coupling.

[structure: see text]. A highly efficient and stereoselective protocol for the syntheses of symmetrical and unsymmetrical carotenoids involving Zr-catalyzed carboalumination of conjugated oligoenynes and Pd- and Zn-catalyzed alkenyl-alkenyl coupling has been developed and applied to the syntheses of beta- and gamma-carotene and vitamin A. gamma-Carotene of > or =99% isomeric purity was prepared in three linear steps (five steps overall) from beta-ionone, enyne 8, (E)-ICH=CHBr, and (E)-Me3SiC triple bond CCH=CHBr in 32% overall yield.