Obtusifolin

Base Information

• Chemical Name: Obtusifolin
• CAS No.: 477-85-0
• Molecular Formula: C₁₆H₁₂O₅
• Molecular Weight: 284.268
• DSSTox Substance ID: DTXSID70197254
• Nikkaji Number: J2.459.934E
• Wikidata: Q27151380
• Metabolomics Workbench ID: 134626
• ChEMBL ID: CHEMBL448400
• Mol file: 477-85-0.mol

Synonyms:obtusifolin

Chemical Property of Obtusifolin

Chemical Property:

• Vapor Pressure: 9.12E-12mmHg at 25°C
• Melting Point: 242-243℃
• Boiling Point: 528°Cat760mmHg
• PKA: 6.60±0.20(Predicted)
• Flash Point: 202.1°C
• PSA: 83.83000
• Density: 1.448g/cm³
• LogP: 2.19020
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 284.06847348
• Heavy Atom Count: 21
• Complexity: 448

Purity/Quality:

95%-98% ^*data from raw suppliers

Obtusifolin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C(=C1O)OC)C(=O)C3=C(C2=O)C=CC=C3O

Technology Process of Obtusifolin

There total 13 articles about Obtusifolin 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: 97.0%

(3R,4S,4aS,9aR)-4a,9a-Dichloro-8-hydroxy-4-methoxy-3-methyl-3,4,4a,9a-tetrahydro-1H-anthracene-2,9,10-trione (127042-39-1) → 1,7-Dihydroxy-8-methoxy-6-methyl-9,10-anthraquinone (477-85-0)

Guidance literature:

With sodium methylate;

DOI:10.1016/S0040-4039(01)93478-1

Reference yield: 95.0%

(1R,4aS,9aR)-9a-Chloro-8-hydroxy-1-methoxy-3-methyl-1,2-bis-trimethylsilanyloxy-1,4,4a,9a-tetrahydro-anthraquinone (108637-81-6) → 1,7-Dihydroxy-8-methoxy-6-methyl-9,10-anthraquinone (477-85-0) + 2-hydroxychrysophanol (58322-78-4)

Guidance literature:

1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(00)85117-5

Reference yield: 13.0%

(1S,4aR,9aS)-8-Hydroxy-1-methoxy-3-methyl-1,2-bis-trimethylsilanyloxy-1,4,4a,9a-tetrahydro-anthraquinone (108637-77-0) → 1,7-Dihydroxy-8-methoxy-6-methyl-9,10-anthraquinone (477-85-0) + 2-hydroxychrysophanol (58322-78-4)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(00)85117-5

upstream raw materials:

5-hydroxynaphtho-1,4-quinone

1-Methoxy-3-methyl-1,2-bis(trimethylsiloxy)-1,3-butadiene

(1S,4aR,9aS)-8-Hydroxy-1-methoxy-3-methyl-1,2-bis-trimethylsilanyloxy-1,4,4a,9a-tetrahydro-anthraquinone

(1R,4aS,9aR)-9a-Chloro-8-hydroxy-1-methoxy-3-methyl-1,2-bis-trimethylsilanyloxy-1,4,4a,9a-tetrahydro-anthraquinone

Downstream raw materials:

2-hydroxychrysophanol

Hallachrome

Refernces

• 1、 Krohn, Carsten,Khanbabaee, Karamali. "Transition Metal-Catalyzed Oxidations, 6. Total Synthesis of Hallachrome and Related 1,2-Anthraquinones". . p. 905 - 910. Retrieved 2007/10/02.
• 2、 Cameron, Donald W.,Feutrill, Geoffrey I.,Gamble, Glenn B.,Stavrakis, John. "SYNTHESIS OF SPECIFICALLY O-ALKYLATED ANTHRAQUINONES BY CYCLOADDITION". . p. 4999 - 5002. Retrieved 2007/10/02.