(+)-ent-Chromazonarol

Base Information

• Chemical Name: (+)-ent-Chromazonarol
• CAS No.: 57457-77-9
• Molecular Formula: C21H30O2
• Molecular Weight: 314.468
• Mol file: 57457-77-9.mol

Synonyms:(+)-ent-Chromazonarol;(4aS)-1,3,4,4a,5,6,6a,12,12aβ,12b-Decahydro-4,4,6aα,12bα-tetramethyl-2H-benzo[a]xanthen-10-ol;(4aS)-4,4,6aα,12bα-Tetramethyl-1,2,3,4,4aβ,5,6,6a,12aβ,12b-decahydro-12H-benzo[a]xanthene-10-ol;ent-Chromazonarol

Chemical Property of (+)-ent-Chromazonarol

Chemical Property:

• PSA: 29.46000
• LogP: 5.32840

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-ent-Chromazonarol

There total 3 articles about (+)-ent-Chromazonarol 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:

4-methoxybenzene-1,3-diol (6100-60-3) → (+)-ent-chromazonarol (57457-77-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dichloromethane / 0.08 h / 20 °C / Inert atmosphere

1.2: 6 h / 20 °C / Inert atmosphere

2.1: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

3.1: sodium formate; tetrabutylammomium bromide; triethylamine / N,N-dimethyl-formamide / 0.5 h / Inert atmosphere

3.2: 8 h / 80 °C / Inert atmosphere

4.1: tris(pentafluorophenyl)borate / toluene; hexane / 24 h / 20 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

With pyridine; tris(pentafluorophenyl)borate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; sodium formate; triethylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1002/ejoc.201601503

Reference yield:

(+)-manool (596-85-0,29461-42-5,41357-91-9,106631-38-3,1438-62-6) → (+)-ent-chromazonarol (57457-77-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: KMnO₄; MgSO₄ / acetone / 20 °C

2.1: 66 percent / oxygen / 1,2-dimethoxy-ethane / 4 h / 20 °C

3.1: 95 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

4.1: 8 percent / molecular sieves 4 Angstroem; N-methylmorpholine N-oxide; tetra-n-propylammonium perruthenate / CH₂Cl₂

5.1: 94 percent / NaHCO₃; m-chloroperbenzoic acid / CH₂Cl₂ / -78 °C

6.1: 95 percent / potassium hydroxide / methanol / 20 °C

7.1: 85 percent / molecular sieves 4 Angstroem; N-methylmorpholine N-oxide; tetra-n-propylammonium perruthenate / CH₂Cl₂

8.1: sec-butyllithium / hexane; tetrahydrofuran / 0 - 20 °C

8.2: 93 percent / hexane; tetrahydrofuran / 1 h

9.1: 94 percent / Li; liq. ammonia / tetrahydrofuran / 0.33 h / -78 °C

10.1: 94 percent / pyridinium p-toluenesulfonate / ethanol / 2 h / 20 °C

11.1: 98 percent / BF₃*Et₂O / CH₂Cl₂ / 0.08 h / 0 °C

With potassium hydroxide; potassium permanganate; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; 4 A molecular sieve; boron trifluoride diethyl etherate; ammonia; sec.-butyllithium; oxygen; pyridinium p-toluenesulfonate; lithium; sodium hydrogencarbonate; magnesium sulfate; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; acetone; 5.1: Baeyer-Villiger oxidation;

DOI:10.1080/00397910500377172

Reference yield:

→ (4aS,12aR,12bS)-4,4,6a,12b-Tetramethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-benzo[a]xanthen-10-ol (57291-88-0,57457-77-9,72937-17-8,144408-26-4)

Guidance literature:

Zonarol 3, BF3-Etherat;

DOI:10.1007/BF02326741

upstream raw materials:

(+)-manool

4-methoxybenzene-1,3-diol

Downstream raw materials:

(+)-yahazunone

(+)-zonarone

ent-isozonarone

(-)-ent-zonarol