Bursehernin

Base Information

• Chemical Name: Bursehernin
• CAS No.: 40456-51-7
• Molecular Formula: C21H22 O6
• Molecular Weight: 370.402
• DSSTox Substance ID: DTXSID50960847
• Nikkaji Number: J322.972F
• Wikidata: Q27162871
• Mol file: 40456-51-7.mol

Synonyms:(3R-trans)-4-(1,3-benzodioxol-5-ylmethyl)-3-((3,4-dimethoxyphenyl)methyl)dihydro-2(3H)-furanone;bursehernin

Chemical Property of Bursehernin

Chemical Property:

• Vapor Pressure: 7.08E-12mmHg at 25°C
• Boiling Point: 543.6°Cat760mmHg
• Flash Point: 238.5°C
• PSA: 63.22000
• Density: 1.268g/cm³
• LogP: 3.00690
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 370.14163842
• Heavy Atom Count: 27
• Complexity: 511

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Bursehernin ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)CC2C(COC2=O)CC3=CC4=C(C=C3)OCO4)OC
• Isomeric SMILES: COC1=C(C=C(C=C1)C[C@@H]2[C@H](COC2=O)CC3=CC4=C(C=C3)OCO4)OC

Technology Process of Bursehernin

There total 42 articles about Bursehernin 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: 99.0%

4-bromomethyl-1,2-dimethoxybenzene (21852-32-4) + (R)-(+)-3-piperonyl-4-butanolide (17187-77-8) → bursehernin (40456-51-7)

Guidance literature:

(R)-(+)-3-piperonyl-4-butanolide; With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; 2,2-diphenylacetic acid; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

4-bromomethyl-1,2-dimethoxybenzene; In tetrahydrofuran; hexane; at -50 - -20 ℃; for 2h; stereoselective reaction;

DOI:10.1002/anie.201503789

Reference yield: 80.0%

C21H22O7 → (3S,4S)-4-(benzo[d][1,3]dioxol-5-ylmethyl)-3-(3,4-dimethoxybenzyl)dihydrofuran-2(3H)-one (40456-51-7,78608-55-6,87727-89-7,126452-80-0)

Guidance literature:

With perchloric acid; hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 60h; under 3040.2 Torr;

DOI:10.1016/j.phytochem.2008.04.002

Reference yield: 77.0%

4-(1,3-benzodioxol-5-ylmethyl)-4,5-dihydrofuran-2(3H)-one (80483-34-7) + 4-bromomethyl-1,2-dimethoxybenzene (21852-32-4) → (3S,4S)-4-(benzo[d][1,3]dioxol-5-ylmethyl)-3-(3,4-dimethoxybenzyl)dihydrofuran-2(3H)-one (40456-51-7,78608-55-6,87727-89-7,126452-80-0)

Guidance literature:

4-(1,3-benzodioxol-5-ylmethyl)-4,5-dihydrofuran-2(3H)-one; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1h; Glovebox; Inert atmosphere;

4-bromomethyl-1,2-dimethoxybenzene; In tetrahydrofuran; at -50 - 20 ℃; for 6h;

DOI:10.1021/acs.joc.8b00184

upstream raw materials:

(-)-kaerophyllin

isokaerophyllin

3-(3,4-dimethoxy-phenyl)-propionyl chloride

3,4-methoxycinnamic acid

Refernces

• 1、 Li, Jian,Zhang, Xiao,Renata, Hans. "Asymmetric Chemoenzymatic Synthesis of (?)-Podophyllotoxin and Related Aryltetralin Lignans". supporting information. p. 11657 - 11660. Retrieved 2019/08/02.
• 2、 Kc, Shekhar,Basnet, Prakash,Thapa, Surendra,Shrestha, Bijay,Giri, Ramesh. "Ni-Catalyzed Regioselective Dicarbofunctionalization of Unactivated Olefins by Tandem Cyclization/Cross-Coupling and Application to the Concise Synthesis of Lignan Natural Products". . p. 2920 - 2936. Retrieved 2018/03/09.