Ardisiaquinone A

Base Information

• Chemical Name: Ardisiaquinone A
• CAS No.: 18799-05-8
• Molecular Formula: C30H40 O8
• Molecular Weight: 528.643
• Nikkaji Number: J16.662F
• Mol file: 18799-05-8.mol

Synonyms:ardisiaquinone A

Chemical Property of Ardisiaquinone A

Chemical Property:

• Vapor Pressure: 7.2E-23mmHg at 25°C
• Boiling Point: 703.4°Cat760mmHg
• Flash Point: 223.7°C
• PSA: 127.20000
• Density: 1.19g/cm³
• LogP: 5.99240
• XLogP3: 7.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 18
• Exact Mass: 528.27231823
• Heavy Atom Count: 38
• Complexity: 957

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=O)C(=C(C1=O)CCCCCCCC=CCCCCCCCC2=C(C(=O)C=C(C2=O)OC)O)O
• Isomeric SMILES: COC1=CC(=O)C(=C(C1=O)CCCCCCC/C=C\CCCCCCCC2=C(C(=O)C=C(C2=O)OC)O)O

Technology Process of Ardisiaquinone A

There total 11 articles about Ardisiaquinone 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: 47.0%

C32H44O8 (99621-90-6) → ardisiaquinone A (18799-05-8)

Guidance literature:

With perchloric acid; In tetrahydrofuran; dichloromethane;

DOI:10.1248/cpb.42.2211

Reference yield:

1,7-dibromoheptane (4549-31-9) → ardisiaquinone A (18799-05-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) n-BuLi, TMEDA, 2.) HMPA / 1.) toluene, -78 deg C, 2.) toluene

2: HMPA / tetrahydrofuran / -78 - 20 °C

3: TBAF

4: 1.) LDA, HMPA / 1.) THF, -78 deg C

5: H₂ / Lindlar catalyst

6: 48percent HBr / methanol

7: 96 percent / O₂, NaHCO₃ / methanol

8: 47 percent / 70percent HClO₄ / CH₂Cl₂; tetrahydrofuran

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; perchloric acid; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; hydrogen bromide; hydrogen; oxygen; sodium hydrogencarbonate; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1248/cpb.42.2211

Reference yield:

2,5-dimethoxyquinone (3117-03-1) → ardisiaquinone A (18799-05-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) Na₂S₂O₄, H₂O, 2.) i-Pr₂NEt / 1.) MeOH, THF, 2.) CH₂Cl₂

2: 1.) n-BuLi, TMEDA, 2.) HMPA / 1.) toluene, -78 deg C, 2.) toluene

3: HMPA / tetrahydrofuran / -78 - 20 °C

4: TBAF

5: 1.) LDA, HMPA / 1.) THF, -78 deg C

6: H₂ / Lindlar catalyst

7: 48percent HBr / methanol

8: 96 percent / O₂, NaHCO₃ / methanol

9: 47 percent / 70percent HClO₄ / CH₂Cl₂; tetrahydrofuran

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; perchloric acid; sodium dithionite; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; water; hydrogen bromide; hydrogen; oxygen; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1248/cpb.42.2211

upstream raw materials:

C₃₂H₄₄O₈

1,7-dibromoheptane

2,5-dimethoxyquinone

1,4-dimethoxy-2,5-di(methoxymethyloxy)benzene

Downstream raw materials:

1,16-Bis-<2-acetoxy-5-methoxy-1,4-benzochinonyl-(3)>-hexadecan

C₃₂H₄₄O₈

1,16-Bis-<2,5-dihydroxy-1,4-benzochinonyl-(3)>-cis-hexadecen-(8)

Dihydroardisiaquinone A

Refernces