Alloxanthoxyletin

Base Information

• Chemical Name: Alloxanthoxyletin
• CAS No.: 731-75-9
• Molecular Formula: C₁₅H₁₄O₄
• Molecular Weight: 258.274
• UNII: 8ZB2VP1WPQ
• DSSTox Substance ID: DTXSID80223371
• Nikkaji Number: J12.505I
• Wikidata: Q27271234
• Metabolomics Workbench ID: 137882
• ChEMBL ID: CHEMBL479462
• Mol file: 731-75-9.mol

Synonyms:5-methoxy-2,2-dimethyl-2H,8H-pyrano(2,3-f)chromen-8-one;alloxanthoxyletin

Chemical Property of Alloxanthoxyletin

Chemical Property:

• PSA: 48.67000
• LogP: 2.98580
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 258.08920892
• Heavy Atom Count: 19
• Complexity: 437

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C=CC2=C(C=C3C(=C2O1)C=CC(=O)O3)OC)C

Technology Process of Alloxanthoxyletin

There total 14 articles about Alloxanthoxyletin 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: 93.0%

7-hydroxy-5',5a'-dimethylpyrano[2',3'-f]-(2H)-chromen-2-one (130364-30-6) + methyl iodide (74-88-4) → alloxanthoxyletin (731-75-9)

Guidance literature:

With potassium carbonate; In acetone; at 56 ℃;

DOI:10.1021/np0497447

Reference yield: 76.0%

3,4-dihydroalloxanthoxyletin (521097-44-9) → alloxanthoxyletin (731-75-9)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene; for 16h; Heating;

DOI:10.1021/ja0286573

Reference yield:

3,5-dihydroxyphenol (108-73-6) → alloxanthoxyletin (731-75-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 60 percent / phosphorus oxychloride; ZnCl₂ / 18 h / 20 °C

2.1: 70 percent / Zn powder; aq. HCl / methanol / 0 - 20 °C

3.1: Pd₂(dba)3; NaOAc; formic acid / 10 h / 25 °C

3.2: 50 percent / K₂CO₃ / acetone / 6 h / Heating

4.1: 76 percent / DDQ / benzene / 16 h / Heating

With hydrogenchloride; formic acid; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; sodium acetate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; zinc; trichlorophosphate; In methanol; benzene; 2.1: Clemmenson reduction;

DOI:10.1021/ja0286573

upstream raw materials:

3,4-dihydroalloxanthoxyletin

7-hydroxy-5',5a'-dimethylpyrano[2',3'-f]-(2H)-chromen-2-one

methyl iodide

5-methoxy-2,2-dimethyl-7-(toluene-4-sulfonyloxy)-chroman-4-one

Refernces

• 1、 Melliou, Eleni,Magiatis, Prokopios,Mitaku, Sofia,Skaltsounis, Alexios-Leandros,Chinou, Efrosini,Chinou, Ioanna. "Natural and synthetic 2,2-dimethylpyranocoumarins with antibacterial activity". . p. 78 - 82. Retrieved 2007/10/03.
• 2、 Tsukayama, Masao,Sakamoto, Tsukasa,Horie, Tokunaru,Masamura, Mitsuo,Nakayama, Mitsuru. "A CONVENIENT SYNTHESIS OF 2,2-DIMETHYLCHROMENES FROM 2,2-DIMETHYLCHROMANONES". . p. 955 - 958. Retrieved 2007/10/02.