3,6-Dimethylhepta-2,5-dien-1-ol

Base Information

• Chemical Name: 3,6-Dimethylhepta-2,5-dien-1-ol
• CAS No.: 43161-23-5
• Molecular Formula: C₉H₁₆O
• Molecular Weight: 140.225
• DSSTox Substance ID: DTXSID80705920
• Mol file: 43161-23-5.mol

Synonyms:3,6-dimethylhepta-2,5-dien-1-ol;43161-23-5;DTXSID80705920

Chemical Property of 3,6-Dimethylhepta-2,5-dien-1-ol

Chemical Property:

• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 140.120115130
• Heavy Atom Count: 10
• Complexity: 139

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC(=CCO)C)C

Technology Process of 3,6-Dimethylhepta-2,5-dien-1-ol

There total 1 articles about 3,6-Dimethylhepta-2,5-dien-1-ol 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: 33.0%

methyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside (19488-49-4) + 4-O-benzoyl-2,3-O-cyclohexylidene-α-L-rhamnopyranosyl bromide (76209-08-0) → (E)-3,6-dimethyl-2,5-heptadien-1-ol (43160-61-8,103606-17-3,43161-23-5) + methyl 4-O-(4-O-benzoyl-2,3-di-O-cyclohexylidene-β-L-rhamnopyranosyl)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (76209-12-6)

Guidance literature:

With molecular sieve; silver carbonate; In dichloromethane; for 2h;

DOI:10.1016/S0008-6215(00)85425-7

Reference yield: 80.0%

(E)-3,6-dimethyl-2,5-heptadien-1-ol (43160-61-8,103606-17-3,43161-23-5) → geranial (96839-90-6)

Guidance literature:

With bichromate of bis(triphenylphosphino)methane; In dichloromethane; at 25 ℃; for 2h;

DOI:10.1016/S0040-4039(00)84371-3

Reference yield:

(E)-3,6-dimethyl-2,5-heptadien-1-ol (43160-61-8,103606-17-3,43161-23-5) → (E)-4-[(2R,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-oxiranyl]-2-methyl-but-2-en-1-ol (565183-89-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: D-(-)-diisopropyl tartrate; Ti(i-PrO)4; t-BuOOH / 4 Angstroem molecular sieves / CH₂Cl₂; decane / -40 - -18 °C

2.1: imidazole / CH₂Cl₂ / 0.5 h / 0 °C

3.1: SeO₂; t-BuOOH; H₂O / CH₂Cl₂ / 48 h / 0 °C

3.2: 75 percent / NaBH₄ / methanol / 1 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; selenium(IV) oxide; water; D-(-)-diisopropyl tartrate; 4 A molecular sieve; In decane; dichloromethane; 1.1: Sharpless asymmetric epoxidation;

DOI:10.1021/ol034539o

upstream raw materials:

methyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside

4-O-benzoyl-2,3-O-cyclohexylidene-α-L-rhamnopyranosyl bromide

Downstream raw materials:

geranial

(2R,3R,5R)-2,3;5,6-diepoxy-3,6-dimethyl-1-O-(N-phenyl)carbamoyl-heptan-1-ol

(2R,3R)-1-O-tert-butyldiphenylsilyl-2,3-epoxy-3,6-dimethyl-5-hepten-1-ol

(E)-4-[(2R,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-oxiranyl]-2-methyl-but-2-en-1-ol