beta-Conidendrin

Base Information

• Chemical Name: beta-Conidendrin
• CAS No.: 5474-93-1
• Molecular Formula: C20H20O6
• Molecular Weight: 356.3692
• UNII: L4NBA667JZ
• Mol file: 5474-93-1.mol

Synonyms:beta-Conidendrin;L4NBA667JZ;.beta.-Conidendrin;UNII-L4NBA667JZ;NSC 4587;Naphtho(2,3-c)furan-1(3H)-one, 3a,4,9,9a-tetrahydro-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxy-, (3aR,4S,9aS)-;NSC-4587;(3AR,4S,9AS)-3A,4,9,9A-TETRAHYDRO-6-HYDROXY-4-(4-HYDROXY-3-METHOXYPHENYL)-7-METHOXYNAPHTHO(2,3-C)FURAN-1(3H)-ONE;(3aS,9S,9aR)-7-hydroxy-9-(4-hydroxy-3-methoxy-phenyl)-6-methoxy-3a,4,9,9a-tetrahydro-1H-benzo[f]isobenzofuran-3-one;Naphtho[2,3-c]furan-1(3H)-one, 3a,4,9,9a-tetrahydro-6-hydroxy-4-(4-hydroxy- 3-methoxyphenyl)-7-methoxy-, (3aR,4S,9aS)-

Chemical Property of beta-Conidendrin

Chemical Property:

• Vapor Pressure: 4.65E-15mmHg at 25°C
• Boiling Point: 601.4°Cat760mmHg
• Flash Point: 218.1°C
• Density: 1.334g/cm³
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 356.12598835
• Heavy Atom Count: 26
• Complexity: 524

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C(C3COC(=O)C3CC2=C1)C4=CC(=C(C=C4)O)OC)O
• Isomeric SMILES: COC1=C(C=C2[C@@H]([C@H]3COC(=O)[C@H]3CC2=C1)C4=CC(=C(C=C4)O)OC)O

Technology Process of beta-Conidendrin

There total 71 articles about beta-Conidendrin 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: 100.0%

(7’S,8R,8’R)-4,4’,7’-trihydroxy-3,3’-dimethoxylignano-9,9’-lactone (20268-71-7,347359-71-1) → conidendrin (518-55-8,5474-93-1,22614-13-7,26358-20-3,85699-62-3,89104-61-0,105817-20-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 25 ℃;

DOI:10.1021/ol049878b

Reference yield: 97.0%

(7RS,8R,8'R)-4,4',7-trihydroxy-3,3'-dimethoxylignano-9,9'-lactone (347359-71-1) → α-conidendrin (518-55-8,5474-93-1,22614-13-7,26358-20-3,85699-62-3,89104-61-0,105817-20-7)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; at 80 ℃; for 0.166667h; Reagent/catalyst; Microwave irradiation;

DOI:10.1021/acs.jnatprod.6b01124

Reference yield: 94.0%

(2R,3R)-(6R,S)-(+)-2-(4-Hydroxy-3-methoxybenzyl)-3-(α-benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide (127951-05-7,128049-88-7,128050-02-2,128050-05-5) → conidendrin (518-55-8,5474-93-1,22614-13-7,26358-20-3,85699-62-3,89104-61-0,105817-20-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; for 0.666667h;

DOI:10.1016/S0040-4020(01)88129-1

upstream raw materials:

(1S,3aR,4S,9aR)-1,7-dimethoxy-4-(4'-hydroxy-3'-methoxyphenyl)-1,3,3a,4,9,9a-hexahydronaphtho<2,3-c>furan-6-ol

(1R,3aR,4S,9aR)-1,7-dimethoxy-4-(4'-hydroxy-3'-methoxyphenyl)-1,3,3a,4,9,9a-hexahydronaphtho<2,3-c>furan-6-ol

(-)-O-6-Benzyl-α-conidendrine

(2R,3R)-(6R,S)-(+)-2-(4-Hydroxy-3-methoxybenzyl)-3-(α-benzyloxy-4-hydroxy-3-methoxybenzyl)butan-4-olide

Downstream raw materials:

(6R,7R,8S)-isolariciresinol

α-conidendrin dimethyl ether

3',4,4',5-tetrahydroxy-2,7'-cyclolignan-9,9'-lactone

α-conidendreic acid dimethyl ester dimethyl ether