Dehydrodieugenol

Base Information

• Chemical Name: Dehydrodieugenol
• CAS No.: 4433-08-3
• Molecular Formula: C20H22O4
• Molecular Weight: 326.39
• Hs Code.: 2922299090
• DSSTox Substance ID: DTXSID80196137
• Nikkaji Number: J111.633I
• Wikidata: Q27106349
• Metabolomics Workbench ID: 68286
• ChEMBL ID: CHEMBL182629
• Mol file: 4433-08-3.mol

Synonyms:dehydro-di-eugenol;dehydrodieugenol

Chemical Property of Dehydrodieugenol

Chemical Property:

• Boiling Point: 439.8oC at 760 mmHg
• Flash Point: 219.8oC
• PSA: 58.92000
• Density: 1.131g/cm3
• LogP: 4.23900
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 326.15180918
• Heavy Atom Count: 24
• Complexity: 372

Purity/Quality:

95% ^*data from raw suppliers

Dieugenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1O)C2=C(C(=CC(=C2)CC=C)OC)O)CC=C
• Uses: Dieugenol is a derivative of magnolol (M110390) and a dimer of eugenol (E938640). Dieugenol is an α-Glucosidase Inhibitor.

Technology Process of Dehydrodieugenol

There total 1 articles about Dehydrodieugenol 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:

methanol (67-56-1) + 4-allylguaiacol (97-53-0) → 5,5'-diallyl-2,2'-dihydroxy-3,3'-dimethoxybiphenyl (4433-08-3) + 2,2-dimethoxy-4-allyl-3,5-cyclohexadien-1-one (67222-39-3) + 4-Allyl-2,4-dimethoxy-cyclohexa-2,5-dienone (67222-38-2)

Guidance literature:

With sodium perchlorate; sodium methylate; at 30 ℃; for 0.333333h; electrolysis;

DOI:10.1021/jo00297a051

Reference yield: 95.0%

5,5'-diallyl-2,2'-dihydroxy-3,3'-dimethoxybiphenyl (4433-08-3) + (1R,2S,5R)-menthyl chloroformate (14602-86-9,7635-53-2) → Carbonic acid 5,5'-diallyl-2'-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxycarbonyloxy)-3,3'-dimethoxy-biphenyl-2-yl ester (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (676270-23-8)

Guidance literature:

With triethylamine; In toluene; at 20 ℃; for 12h;

DOI:10.1016/j.tetasy.2003.11.020

Reference yield: 63.0%

5,5'-diallyl-2,2'-dihydroxy-3,3'-dimethoxybiphenyl (4433-08-3) + 1-tosyloxy-1-vinylcyclopropane (32364-41-3) → 3,3'-dimethoxy-5,5'-di(2-propenyl)-2-(1-ethenylcyclopropyloxy)-2'-hydroxybiphenyl + 2-(2-cyclopropylideneethoxy)-3,3'-dimethoxy-5,5'-di(2-propenyl)biphenyl-2'-hydroxybiphenyl + 2,2'-bis(2-cyclopropylideneethoxy)-3,3'-dimethoxy-5,5'-di(2-propenyl)biphenyl-2'-hydroxybiphenyl

Guidance literature:

5,5'-diallyl-2,2'-dihydroxy-3,3'-dimethoxybiphenyl; With potassium carbonate; In N,N-dimethyl-formamide; at 60 ℃; for 1h;

1-tosyloxy-1-vinylcyclopropane; With triphenylphosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 20 ℃; for 20h;

DOI:10.1055/s-2002-34950

upstream raw materials:

methanol

4-allylguaiacol

Downstream raw materials:

Carbonic acid 5,5'-diallyl-2'-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxycarbonyloxy)-3,3'-dimethoxy-biphenyl-2-yl ester (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Refernces