17974-59-3

Usage

Pentenynol functional group

The molecule contains a pentenynol functional group, which consists of a five-carbon chain with a triple bond and a hydroxyl group.

Cyclohexenyl group

The molecule also includes a cyclohexenyl group, which is a six-carbon ring with a double bond.

3-Methyl substituent

A methyl group (CH3) is attached to the cyclohexenyl group at the 3-position, which adds complexity to the molecule.

2,6,6-Trimethyl substituents

Three methyl groups (CH3) are attached to the cyclohexenyl group at the 2and 6-positions, which further adds complexity to the molecule.

(1E)designation

The molecule has a cis configuration at the double bond, which means that the two substituents on the double bond are on the same side of the molecule.

Applications in organic chemistry

The compound may be used in the synthesis of pharmaceuticals or other complex organic molecules.

Upstream product

• 79-77-6 (E)-β-ionone 
• 74-86-2 acetylene 
• 4301-14-8 acetylenemagnesium bromide 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 70277-75-7 lithium acetylide 

Downstream Products

• 95286-43-4 ethyl 9-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-3,7-dimethyl-4,7-dihydroxy-(2E,8E)-nona-2,8-dien-5-ynoate 
• 142893-63-8 8-(1,3-dithian-2-yl)-3,7-dimethyl-1-(2,6,6-trimethyl-cyclohex-1-enyl)octa-1E,7E-dien-4-yne-3,6-diol 
• 118304-63-5 methyl 9-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-4,7-dihydroxy-3,7-dimethyl-(2Z,8E)-nona-2,8-dien-5-ynoate 
• 119947-51-2 5-[(E)-3-Hydroxy-3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-pent-4-en-1-ynyl]-4-methyl-5H-furan-2-one 
• 53839-93-3 9-(1-deuterovinyl)-β-ionol 
• 83060-53-1 (1Z)-3-methyl-1-(2',2',6'-trimethylcyclohex-1'-enyl)-1-penten-4-yn-3-ol 
• 4759-48-2 13-cis-retinoic acid 
• 472-86-6 13-cis-vitamin A aldehyde 
• 116-31-4 all-trans-Retinal 
• 302-79-4 all-trans-retinoic-acid 
• 16760-45-5 (2Z,4E,6E,8E)-methyl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate 
• 339-16-2 all-trans-methyl retinoate 
• 142893-61-6 all-trans-retinal propylene dithioacetal 
• 142893-62-7 8-(1,3-dithian-2-yl)-3,7-dimethyl-1-(2,6,6-trimethyl-cyclohex-1-enyl)octa-1E,4E,7E-trien-3,6-diol 

Relevant academic research and scientific papers

CATALYTIC ETHYNYLATION

The present invention relates to the catalytic ethynlation of αβ-unsaturated ketones for producing tertiary acetylenic alcohols.

METHOD FOR THE PRODUCTION OF ACETYLENE ALCOHOLS

The invention relates to a method for producing acetylene alcohols of general formula (I), wherein R1, R2 can independently be identical or different and represent optionally substituted hydrogen, an optionally substituted saturated, monounsaturated or polyunsaturated C1-C30 alkyl radical, aryl radical, cycloalkylalkyl radical, or cycloalkyl radical, or a group of general formula (II), wherein R3, R4 can independently be identical or different and represent optionally substituted hydrogen or an optionally substituted saturated, monounsaturated, or polyunsaturated C1-C30 alkyl radical, aryl radical, cycloalkylalkyl radical, or cycloalkyl radical while the dashed line can represent an additional double bond. Said acetylene alcohols are produced by monoethynylating a ketone of general formula R1-CO-R2 by (a) reacting lithium with a C1-C10 alkyl halide, (b) introducing acetylene gas, and (c) adding the ketone.

HIGHLY STEREOSELECTIVE SYNTHESIS OF VITAMIN A AND ALL-TRANS RETINOIC ACID BY LOW-VALENT TITANIUM INDUCED REDUCTIVE ELIMINATION

Application of the low-valent Titanium induced reductive elimination gave a new and highly stereoselective approach to vitamin A and all-trans retinoic acid.

Thermal Sigmatropic Rearrangements of Vinylallenes Leading to 11-cis-Retinoids and the Novel Properties of 9-cis,11-cis,13-cis-Retinal and 11-cis,13-cis-Retinal

The thermally induced sigmatropic hydrogen shift of vinylallene 5 provided a route to highly hindered 11-cis-retinoids.The coupling ot the hetero cuprate 14 with the propargyl benzoate 13b gave the vinylallene 5, which upon heating (69 deg C, 2 h) gave three geometrically isomeric retinoids: 11-sis (8), 11-cis,13-cis (9), and 9-cis,11-cis,13-cis (11).The fourth possible geometric isomer, 9-cis,11-cis (10), was unstable to the conditions of thermolysis and underwent further electrocyclizations to the tricyclic compound 22.The thermal rearramgement of 9,10-allene 5, though highly specific for the formation of 11-cis-retinoids, exhibits no selectivity in the formation of Δ9 and Δ13 double bonds.The highly hindered 11-cis,13-cis- and 9-cis,11-cis,13-cis-retinals, 9b and 11b, exhibit extraordinary electronic absorption spectra in that they exhibit their main maxima (302 nm) actually to the blue of the corresponding alcohols.The retinals 9b and 11b were thermally unstable and underwent clean isomerization to 13-cis-retinal and 9-cis,13-cis-retinal, respectively.

10-Mono-, 11-mono-, 12-mono and 11,12-dideuteroretinal

The 11-mono and 12-mono- and 11,12-dideuteroretinal (in the all-trans, 9-cis, 11-cis and 13-cis form) with > 98percent chemical purity and > 95percent mono- and dideuterium incorporation were prepared using the same scheme for all three compounds.The all-

Catalytic rearrangement

Process for converting secondary and tertiary acetylenic carbinols to the corresponding alpha,beta-unsaturated carbonyl compounds by rearranging the carbinol with (trilower alkyl-, tricycloalkyl-, triaryl- or triarylalkyl-siloxy)-vanadium oxide catalyst in the presence of a silanol where either the vanadium oxide or the silanol contains a phenyl group substituted with at least one electron withdrawing group.