(3R,3aS,6R,6aS,10aS)-3,6,9-trimethyl-3,3a,4,5,6,6a,7,8-octahydrobenzo[h][1]benzofuran-2-one

Base Information

• Chemical Name: (3R,3aS,6R,6aS,10aS)-3,6,9-trimethyl-3,3a,4,5,6,6a,7,8-octahydrobenzo[h][1]benzofuran-2-one
• CAS No.: 104196-16-9
• Molecular Formula: C₁₅H₂₂O₂
• Molecular Weight: 234.338
• DSSTox Substance ID: DTXSID701118388
• Nikkaji Number: J1.280.440G
• Wikidata: Q105263047
• Mol file: 104196-16-9.mol

Synonyms:SCHEMBL13771046;DTXSID701118388;104196-16-9;(3R,3aS,6R,6aS,10aS)-3,3a,4,5,6,6a,7,8-Octahydro-3,6,9-trimethyl-2H-naphtho[8a,1-b]furan-2-one

Chemical Property of (3R,3aS,6R,6aS,10aS)-3,6,9-trimethyl-3,3a,4,5,6,6a,7,8-octahydrobenzo[h][1]benzofuran-2-one

Chemical Property:

• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 234.161979940
• Heavy Atom Count: 17
• Complexity: 384

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CCC2C(C(=O)OC23C1CCC(=C3)C)C
• Isomeric SMILES: C[C@@H]1CC[C@H]2[C@H](C(=O)O[C@@]23[C@H]1CCC(=C3)C)C

Technology Process of (3R,3aS,6R,6aS,10aS)-3,6,9-trimethyl-3,3a,4,5,6,6a,7,8-octahydrobenzo[h][1]benzofuran-2-one

There total 11 articles about (3R,3aS,6R,6aS,10aS)-3,6,9-trimethyl-3,3a,4,5,6,6a,7,8-octahydrobenzo[h][1]benzofuran-2-one 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: 81.0%

4α-hydroperoxy-amorph-5-en-12-oic acid (85031-60-3) → C12H13O2(CH3)3(O)(OO) (63968-64-9) + (3R,3a,6R,6aS,10aS)-3a,4,5,6,6a,7,8,8a-octahydro-3,6,9-trimethylnaphtho[8a,1-b]furan-2(3H)-one (104196-16-9)

Guidance literature:

With oxygen; trifluoroacetic acid; In toluene; chemoselective reaction; Flow reactor;

DOI:10.1002/chem.201204558

Reference yield: 47.0%

dihydroartemisinic acid (85031-59-0,110715-68-9,126643-10-5) → C12H13O2(CH3)3(O)(OO) (63968-64-9) + (3R,3a,6R,6aS,10aS)-3a,4,5,6,6a,7,8,8a-octahydro-3,6,9-trimethylnaphtho[8a,1-b]furan-2(3H)-one (104196-16-9) + arteanniun H (207446-83-1)

Guidance literature:

dihydroartemisinic acid; With oxygen; 5,15,10,20-tetraphenylporphyrin; In dichloromethane; Irradiation; High pressure;

With oxygen; trifluoroacetic acid; In dichloromethane; toluene; at 50 ℃; for 0.333333h;

Reference yield: 31.2%

dihydroartemisinic acid (85031-59-0,110715-68-9,126643-10-5) → C12H13O2(CH3)3(O)(OO) (63968-64-9) + (3R,3a,6R,6aS,10aS)-3a,4,5,6,6a,7,8,8a-octahydro-3,6,9-trimethylnaphtho[8a,1-b]furan-2(3H)-one (104196-16-9) + (4R,4aS,7R,8S)-4,7-Dimethyl-8-(3-oxo-butyl)-4,4a,5,6,7,8-hexahydro-isochromen-3-one (105231-07-0) + arteanniun H (207446-83-1)

Guidance literature:

dihydroartemisinic acid; With oxygen; 5,15,10,20-tetraphenylporphyrin; In dichloromethane; Irradiation; High pressure;

With oxygen; trifluoroacetic acid; In dichloromethane; toluene; at 75 ℃; for 0.333333h;

upstream raw materials:

dihydroartemisinic acid

4α-hydroperoxy-amorph-5-en-12-oic acid

(1R,5S,8R,9S,12R,14R)-8,12-dimethyl-4-methylidene-2,13-dioxatetracyclo[7.5.0.0^1,5.0^12,14]tetradecan-3-one

dihydroartemisinic acid

Downstream raw materials:

(-)-arteannuin M

(+)-artemisinin

2-(2-(3-((2R)-methoxymethylcarbonylpropyl)-2-methoxymethyloxymethylene-(6R)-methylcyclohex-(1S)-yl)ethyl)-2-methyl-1,3-dioxolane

2-(2-(3-(3-hydroxy-(2R)-methylpropyl)-2-methoxymethoxymethylene-(6R)-methylcyclohex-(1S)-yl)ethyl)-2-methyl-1,3-dioxolane