all-trans-Retinonitrile

Base Information

• Chemical Name: all-trans-Retinonitrile
• CAS No.: 20638-88-4
• Molecular Formula: C20H27N
• Molecular Weight: 281.441
• DSSTox Substance ID: DTXSID80431651
• Nikkaji Number: J1.561.136G,J1.735.787E
• Wikidata: Q82245591
• Mol file: 20638-88-4.mol

Synonyms:all-trans-Retinonitrile;20638-88-4;(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenenitrile;SCHEMBL12713331;DTXSID80431651;J-013486;3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetrenenitrile;(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetrenenitrile

Chemical Property of all-trans-Retinonitrile

Chemical Property:

• PSA: 23.79000
• LogP: 6.04158
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 281.214349865
• Heavy Atom Count: 21
• Complexity: 568

Purity/Quality:

97% ^*data from raw suppliers

all-trans-Retinonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC#N)C)C
• Isomeric SMILES: CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C#N)/C)/C
• Uses: Retinal intermediate.

Technology Process of all-trans-Retinonitrile

There total 43 articles about all-trans-Retinonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

all-trans-retinaldoxime (67890-46-4) → 9-trans-13-trans-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-7,9,11,13-nonatetraene-15-nitrile (20638-88-4)

Guidance literature:

With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; 4 A molecular sieve; In acetonitrile; at 80 ℃; for 0.166667h;

DOI:10.1021/ol0168768

Reference yield: 93.0%

(4E,6E,8E)-3,7,dimethyl-3-acetoxy-9-(2,6,6-trimethyl-1-cyclohexyl)-4,6,8-nonatrienenitrile → 9-trans-13-trans-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-7,9,11,13-nonatetraene-15-nitrile (20638-88-4)

Guidance literature:

With 2,6-dichloro-benzonitrile; In toluene; for 1.5h; Heating;

Reference yield: 78.3%

all-trans-Retinal (116-31-4) → 9-trans-13-trans-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-7,9,11,13-nonatetraene-15-nitrile (20638-88-4)

Guidance literature:

With ammonium heptamolybdate; ammonium hydroxide; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 20 ℃; for 24h;

upstream raw materials:

(3E,5E,7E)-6-methyl-8-(2,6,6-trimethyl-1-cyclohexenyl)-3,5,7-octatriene-2-one

cyanoacetic acid

all-trans-Retinal

9,14-dihydroxy-9,13-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-10,12-nonadiene-15-nitrile

Downstream raw materials:

all-trans-Retinal

(2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenenitrile

(2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenenitrile

9-trans-13-cis-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-7,9,11,13-nonatetraene-15-nitrile