Anolignan A

Base Information

• Chemical Name: Anolignan A
• CAS No.: 158081-97-1
• Molecular Formula: C₁₉H₁₈O₄
• Molecular Weight: 310.35
• NSC Number: 665937
• UNII: F7IFG6J8RN
• DSSTox Substance ID: DTXSID60166373
• Nikkaji Number: J608.191F
• Wikidata: Q27133854
• Metabolomics Workbench ID: 63854
• ChEMBL ID: CHEMBL459395
• Mol file: 158081-97-1.mol

Synonyms:2-(2',4'-dihydroxybenzyl)-3-(3'',4''-methylenedioxybenzyl)-1,3-butadiene;anolignan A

Chemical Property of Anolignan A

Chemical Property:

• Vapor Pressure: 3.79E-11mmHg at 25°C
• Boiling Point: 513.1°Cat760mmHg
• PKA: 9.77±0.35(Predicted)
• Flash Point: 264.1°C
• PSA: 58.92000
• Density: 1.257g/cm³
• LogP: 3.72410
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 310.12050905
• Heavy Atom Count: 23
• Complexity: 447

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C(CC1=CC2=C(C=C1)OCO2)C(=C)CC3=C(C=C(C=C3)O)O

Technology Process of Anolignan A

There total 18 articles about Anolignan A 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: 92.0%

acetic acid 4-(3-benzo[1,3]dioxol-5-ylmethyl-2-methylene-but-3-enyl)-3-hydroxy-phenyl ester (290362-02-6) → anolignan A (158081-97-1)

Guidance literature:

With sodium hydroxide; In methanol;

DOI:10.1016/S0040-4039(00)00604-3

Reference yield: 66.0%

methanesulfonic acid 4-(3-benzo[1,3]dioxol-5-ylmethyl-2-methylenebut-3-enyl)-3-methanesulfonyloxyphenyl ester (397872-60-5) → anolignan A (158081-97-1)

Guidance literature:

With phenyllithium; In diethyl ether; at 20 ℃; for 3.5h;

DOI:10.1021/jo0107913

Reference yield:

piperonal (120-57-0,30024-74-9) → anolignan A (158081-97-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: tetrahydrofuran; hexane / 2 h / -78 °C

2.1: 2.23 g / Bu₄NF / tetrahydrofuran; hexane / 0.5 h / 0 °C

3.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: 66 percent / tetrahydrofuran; hexane / 3 h / -78 °C

4.1: 95 percent / pyridine / CH₂Cl₂ / 20 °C

5.1: 86 percent / PhCH=Ru(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Cl₂ / toluene / 36 h / 80 °C

6.1: 89 percent / formic acid; triethylamine; n-tributylphosphine / Pd₂(dba)3*CHCl₃ / tetrahydrofuran / 1.5 h / 75 °C

7.1: 66 percent / PhLi / diethyl ether / 3.5 h / 20 °C

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; n-butyllithium; formic acid; tributylphosphine; tetrabutyl ammonium fluoride; phenyllithium; triethylamine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;

DOI:10.1021/jo0107913

upstream raw materials:

acetic acid 4-(3-benzo[1,3]dioxol-5-ylmethyl-2-methylene-but-3-enyl)-3-hydroxy-phenyl ester

methanesulfonic acid 4-(3-benzo[1,3]dioxol-5-ylmethyl-2-methylenebut-3-enyl)-3-methanesulfonyloxyphenyl ester

piperonal

1-(benzo[d][1,3]dioxol-5-yl)prop-2-yn-1-ol