halenaquinol

Base Information

• Chemical Name: halenaquinol
• CAS No.: 96603-02-0
• Molecular Formula: C₂₀H₁₄O₅
• Molecular Weight: 334.328
• Mol file: 96603-02-0.mol

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

Chemical Property of halenaquinol

Chemical Property:

• PSA: 87.74000
• LogP: 3.67090

Purity/Quality:

HALENAQUINOL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of halenaquinol

There total 21 articles about halenaquinol 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%

(+)-halenaquinone (86690-14-4) → halenaquinol (96603-02-0)

Guidance literature:

With sodium dithionite; In water; acetone; at 0 ℃;

DOI:10.1021/jo960773z

Reference yield:

(+)-Halenaquinol dimethyl ether (99463-22-6) → halenaquinol (96603-02-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / CAN / methanol; H₂O / 0 °C

2: 100 percent / Na₂S₂O₄ / acetone; H₂O / 0 °C

With sodium dithionite; ammonium cerium(IV) nitrate; In methanol; water; acetone;

DOI:10.1021/jo960773z

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) → halenaquinol (96603-02-0)

Guidance literature:

Multi-step reaction with 13 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

13: aq. sodium hydrosulfite / acetone / 0.5 h

With pyridine; 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; sodium disulfite; 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; acetone; benzene;

DOI:10.1021/ja00233a026

upstream raw materials:

(+)-halenaquinone

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

(+)-Halenaquinol dimethyl ether

(S)-8,11-Dimethoxy-12b-methyl-4-triisopropylsilanyl-1,12b-dihydro-2H-5-oxa-benzo[k]acephenanthrylene-3,6-dione

Downstream raw materials:

halenaquinone

Refernces

• 1、 Kojima, Akihiko,Takemoto, Toshiyasu,Sodeoka, Mikiko,Shibasaki, Masakatsu. "Catalytic asymmetric synthesis of halenaquinone and halenaquinol". . p. 4876 - 4877. Retrieved 2007/10/03.