(+/-)-atractylon

Base Information

• Chemical Name: (+/-)-atractylon
• CAS No.: 3484-43-3
• Molecular Formula: C₁₅H₂₀O
• Molecular Weight: 216.323
• Mol file: 3484-43-3.mol

Synonyms:

Chemical Property of (+/-)-atractylon

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-atractylon

There total 24 articles about (+/-)-atractylon 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: 58.0%

4aα,5,6,7,8,8a,9,9aβ-octahydro-3-methyl-5-methylenenaphtho<2,3-b>furan-2(4H)-one (3241-66-5,16641-51-3,73069-14-4,74111-89-0,94163-11-8) → (+/-)-atractylon (3484-43-3,6989-21-5,98309-94-5)

Guidance literature:

With diisobutylaluminium hydride;

DOI:10.1021/jo0488053

Reference yield:

1,2,3,4,5,8-hexahydro-1-oxo-6-methoxynaphthalene (2844-80-6) → (+/-)-atractylon (3484-43-3,6989-21-5,98309-94-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: CuI

2.1: TBAF

3.1: sodium hydride; dimethyl sulfoxide / 0.25 h / 20 °C

3.2: dimethylsulfoxide / 18 h / 55 °C

4.1: 4.38 g / aq. HCl / diethyl ether / 18 h / 20 °C

5.2: water

6.1: KOH / methanol / 2 h / 20 °C

7.1: 240 mg / sodium acetate; acetic anhydride / 2 h / 155 °C

8.1: 58 percent / Dibal-H

With hydrogenchloride; potassium hydroxide; tetrabutyl ammonium fluoride; sodium acetate; acetic anhydride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; copper(l) iodide; In methanol; diethyl ether; 3.2: Wittig reaction;

DOI:10.1021/jo0488053

Reference yield:

1,2,3,4,5,8-hexahydro-1-hydroxy-6-methoxynaphthalene (1201-61-2) → (+/-)-atractylon (3484-43-3,6989-21-5,98309-94-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 84 percent / acetone; Al(OiPr)3

2.1: CuI

3.1: TBAF

4.1: sodium hydride; dimethyl sulfoxide / 0.25 h / 20 °C

4.2: dimethylsulfoxide / 18 h / 55 °C

5.1: 4.38 g / aq. HCl / diethyl ether / 18 h / 20 °C

6.2: water

7.1: KOH / methanol / 2 h / 20 °C

8.1: 240 mg / sodium acetate; acetic anhydride / 2 h / 155 °C

9.1: 58 percent / Dibal-H

With hydrogenchloride; potassium hydroxide; tetrabutyl ammonium fluoride; sodium acetate; acetic anhydride; aluminum isopropoxide; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; acetone; copper(l) iodide; In methanol; diethyl ether; 1.1: Oppenauer oxidation / 4.2: Wittig reaction;

DOI:10.1021/jo0488053

upstream raw materials:

1-hydroxypropan-2-one tetrahydropyran ether

(+/-)-8a-methyl-5-methylene-octahydro-naphthalen-2(1H)-one

4aα,5,6,7,8,8a,9,9aβ-octahydro-3-methyl-5-methylenenaphtho<2,3-b>furan-2(4H)-one

1,2,3,4,5,8-hexahydro-1-oxo-6-methoxynaphthalene

Downstream raw materials:

4aα,5,6,7,8,8a,9,9aβ-octahydro-3-methyl-5-methylenenaphtho<2,3-b>furan-2(4H)-one

9a-hydroxy-3,8a-dimethyl-5-methylene-4a,5,6,7,8,8a,9,9a-octahydro-4H-naphtho[2,3-b]furan-2-one

(+/-)-3,8a,3',8'a-tetramethyl-5,5'-dimethylene-4,4a,5,6,7,8,8a,9,4',4'a,5',6',7',8',8'a,9'-hexadecahydro-[9a,9'a]bi[naphtho[2,3-b]furanyl]-2,2'-dione

3,8a,3',8'a-tetramethyl-5,5'-dimethylene-4,4a,5,6,7,8,8a,9,4',4'a,5',6',7',8',8'a,9'-hexadecahydro[9a,9'a]bi[naphtho[2,3-b]furanyl]-2,2'-dione

Refernces

• 1、 Gavagnin, Margherita,Mollo, Ernesto,Castelluccio, Francesco,Crispino, Antonio,Cimino, Guido. "Sesquiterpene Metabolites of the Antarctic Gorgonian Dasystenella acanthina". . p. 1517 - 1519. Retrieved 2007/10/03.
• 2、 Schultz, Arthur G.,Godfrey, Jollie D.. "An Annelation Approach to the Synthesis of Eudesmane and Elemane Sesquiterpene Lactones. Total Synthesis of dl-Dihydrocallitrisin, dl-7,8-Epialantolactone, dl-7,8-Epiisoalantolactone, and dl-Atractylon". . p. 2414 - 2428. Retrieved 2007/10/02.