Halenaquinone

Base Information

• Chemical Name: Halenaquinone
• CAS No.: 86690-14-4
• Molecular Formula: C20H12O5
• Molecular Weight: 332.312
• Mol file: 86690-14-4.mol

Synonyms:(+)-halenaquinone;(12bs)-12b-methyl-1h-tetrapheno[5,4-bc]furan-3,6,8,11(2h,12bh)-tetrone;12b-methyl-(S)-1H-benzo[6,7]phenanthro[10,1-bc]furan-3,6,8,11(2H,12bH)-tetrone;helenaquinone;

Chemical Property of Halenaquinone

Chemical Property:

• Vapor Pressure: 2.06E-14mmHg at 25°C
• Boiling Point: 601.2°C at 760 mmHg
• Flash Point: 302.7°C
• PSA: 81.42000
• Density: 1.501g/cm³
• LogP: 3.04170

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Halenaquinone

There total 21 articles about Halenaquinone 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%

8,11-Dimethoxy-12b-methyl-1,12b-dihydro-2H-5-oxa-benzo[k]acephenanthrylene-3,6-dione (344285-19-4) → (+)-halenaquinone (86690-14-4)

Guidance literature:

With ammonium cerium(IV) nitrate; In acetonitrile; for 0.166667h; Ambient temperature;

DOI:10.1055/s-1998-5939

Reference yield: 52.0%

(+)-Halenaquinol dimethyl ether (99463-22-6) → (+)-halenaquinone (86690-14-4)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; at 0 ℃; for 0.166667h;

DOI:10.1016/S0968-0896(03)00276-1

Reference yield:

(4aR,5S,8aR)-3,4,4a,5,8,8a-hexahydro-5-(hydroxymethyl)-8a-methyl-1,6-(2H,7H)-naphthalenedione 1-ethylene acetal (117439-20-0) → (+)-halenaquinone (86690-14-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 92 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 0.33 h / 0 °C

2: 98 percent / p-toluenesulfonic acid monohydrate / H₂O / 3 h / Ambient temperature

3: 13.0 g / ethanol / 4 h / Heating

4: methyllithium / diethyl ether; tetrahydrofuran / 1 h / Ambient temperature

5: 86 percent / p-toluenesulfonic acid, triethylamine / 4 h / Ambient temperature

6: 63 percent / chromium(VI) oxide, 3,5-dimethylpyrazole / CH₂Cl₂ / 2.5 h / -20 °C

7: 33 percent / benzene / 20 h / 210 - 215 °C

8: 89 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / benzene / 3.5 h / Heating

9: 90 percent / potassium tert-butoxide, tert-butyl alcohol, oxygen / 4 h / Ambient temperature

10: 0.071 g / 60 percent aq. acetic acid / 0.5 h / Ambient temperature

11: 44 percent / pyridine, 1,3-dicyclohexylcarbodiimide (DCC), trifluoroacetic acid / dimethylsulfoxide; benzene / 20 h / Ambient temperature

12: 45 percent / cerium(IV) ammonium nitrate (CAN) / methanol; H₂O / 1.) 2 h, 2.) 1 h, room temperature

With pyridine; 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; ammonium cerium(IV) nitrate; potassium tert-butylate; methyllithium; oxygen; L-Selectride; toluene-4-sulfonic acid; acetic acid; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tert-butyl alcohol; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; benzene;

DOI:10.1021/ja00233a026

upstream raw materials:

halenaquinol

halenaquinol sulfate

(+)-Halenaquinol dimethyl ether

8,11-Dimethoxy-12b-methyl-1,12b-dihydro-2H-5-oxa-benzo[k]acephenanthrylene-3,6-dione

Downstream raw materials:

C₂₈H₂₃NO₅

halenaquinol

Refernces

Vinyl quinones as Diels-Alder dienes: Concise synthesis of (-)-halenaquinone

10.1021/ja8035042

The research describes a concise and asymmetric synthesis of (-)-halenaquinone, a pentacyclic natural product with significant interest due to its unique structure and diverse bioactivity. The synthesis strategy hinges on an intramolecular inverse-electron-demand Diels-Alder reaction involving a vinyl quinone, a novel application of the Diels-Alder reaction. Key chemicals used in the process include iodofuran 9, silyl ether, vinyl stannane 12, and silver(II) oxide, among others. The study successfully demonstrated the viability of vinyl quinones as dienes in intramolecular Diels-Alder reactions and explored potential transition states through DFT calculations. The synthesis concluded with the oxidation and aromatization of the pentacyclic hydroquinone 17 to yield (-)-halenaquinone, which was found to be identical to the natural product in all respects except for its optical rotation. The research also highlighted the regioselective lithiation and formylation of a 3-iodofuran, enabling a highly diastereoselective intramolecular Heck cyclization, and the potential for further applications of vinyl quinone cycloadditions in total synthesis is under investigation.