4,8,12-Tetradecatrienal, 14-hydroxy-4,8,12-trimethyl-, (4E,8E,12E)-

Base Information

• Chemical Name: 4,8,12-Tetradecatrienal, 14-hydroxy-4,8,12-trimethyl-, (4E,8E,12E)-
• CAS No.: 87920-56-7
• Molecular Formula: C17H28O2
• Molecular Weight: 264.408
• Mol file: 87920-56-7.mol

Synonyms:

Chemical Property of 4,8,12-Tetradecatrienal, 14-hydroxy-4,8,12-trimethyl-, (4E,8E,12E)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,8,12-Tetradecatrienal, 14-hydroxy-4,8,12-trimethyl-, (4E,8E,12E)-

There total 2 articles about 4,8,12-Tetradecatrienal, 14-hydroxy-4,8,12-trimethyl-, (4E,8E,12E)- 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:

diazomethane (186581-53-3,908094-01-9,334-88-3) + 3,5-dibromo-4-(di-tert-butyl(nonaprenyloxy)silyloxy)benzoic acid (1033756-53-4) → farnesylfarnesylacetone (32304-17-9) + geranylfarnesylacetone (86541-61-9) + C22H36O2 (869878-11-5) + 10-hydroxy-4,8-dimethyldeca-4,8-dienal (87920-55-6) + methyl 3,5-dibromo-4-hydroxybenzoate (41727-47-3) + (4E,8E,12E)-14-hydroxy-4,8,12-trimethyltetradeca-4,8,12-trienal (87920-56-7) + 5E,9E,13E-geranylgeranyl acetone (6809-52-5)

Guidance literature:

3,5-dibromo-4-(di-tert-butyl(nonaprenyloxy)silyloxy)benzoic acid; With 1,1'-carbonyldiimidazole; In dichloromethane; at 23 ℃; for 0.5h;

With dihydrogen peroxide; In dichloromethane; at -78 - -20 ℃;

diazomethane; With tetrabutylammonium periodite; pyridine hydrogenfluoride; periodic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; Further stages;

DOI:10.1021/ja801899v

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + 4'-(di-tert-butyl(nonaprenyloxy)silyloxy)-2,6-dinitrobiphenyl-4-carboxylic acid (1033756-63-6) → methyl 4'-hydroxy-2,6-dinitrobiphenyl-4-carboxylate (194548-45-3) + 6,10,14-trimethyl-5,9,13-pentadecatriene-2-on (1117-52-8) + geranylfarnesylacetone (86541-61-9) + C22H36O2 (869878-11-5) + (4E,8E,12E)-14-hydroxy-4,8,12-trimethyltetradeca-4,8,12-trienal (87920-56-7) + (4E,8E,12E,16E,20E)-22-Hydroxy-4,8,12,16,20-pentamethyl-docosa-4,8,12,16,20-pentaenal (869878-12-6) + 5E,9E,13E-geranylgeranyl acetone (6809-52-5)

Guidance literature:

4'-(di-tert-butyl(nonaprenyloxy)silyloxy)-2,6-dinitrobiphenyl-4-carboxylic acid; With 1,1'-carbonyldiimidazole; In dichloromethane; at 23 ℃; for 0.5h;

With dihydrogen peroxide; In dichloromethane; at -78 - -20 ℃;

diazomethane; With tetrabutylammonium periodite; pyridine hydrogenfluoride; periodic acid; In tetrahydrofuran; dichloromethane; water; Further stages;

DOI:10.1021/ja801899v

Reference yield:

(4E,8E,12E)-14-hydroxy-4,8,12-trimethyltetradeca-4,8,12-trienal (87920-56-7) → Se-phenyl (E,E,E)-5,9,13-trimethyl-15-[(tetrahydro-2H-pyran-2-yl)oxy]pentadeca-5,9,13-trieneselenoate (314739-79-2)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridinium p-toluenesulfonate / CH₂Cl₂ / 8 h / 20 °C

2: 752 mg / NaBH₄ / methanol; diethyl ether / 16 h / 20 °C

3: Et₃N / CH₂Cl₂ / 2 h / 0 °C

4: 467 mg / dimethylsulfoxide / 18 h / 60 °C

5: 81 percent / DIBAL-H / toluene / 5 h / -78 °C

6: 99 percent / NaClO₂; KH₂PO₄; 2-methylbut-2-ene / H₂O; 2-methyl-propan-2-ol / 1 h

7: 71 percent / Bu₃P / CH₂Cl₂ / 0.5 h / -30 °C

With sodium chlorite; sodium tetrahydroborate; potassium dihydrogenphosphate; 2-methyl-but-2-ene; tributylphosphine; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; In methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; toluene; tert-butyl alcohol; 1: Addition / 2: Reduction / 3: Condensation / 4: Substitution / 5: Reduction / 6: Oxidation / 7: Substitution;

DOI:10.1002/1522-2675(20000906)83:9<2629::AID-HLCA2629>3.0.CO;2-W

upstream raw materials:

diazomethane

3,5-dibromo-4-(di-tert-butyl(nonaprenyloxy)silyloxy)benzoic acid

4'-(di-tert-butyl(nonaprenyloxy)silyloxy)-2,6-dinitrobiphenyl-4-carboxylic acid

Downstream raw materials:

Se-phenyl (E,E,E)-15-hydroxy-5,9,13-trimethylpentadeca-5,9,13-trieneselenoate

Se-phenyl (E,E,E)-5,9,13-trimethyl-15-[(tetrahydro-2H-pyran-2-yl)oxy]pentadeca-5,9,13-trieneselenoate