Petasitolone

Base Information

• Chemical Name: Petasitolone
• CAS No.: 35124-22-2
• Molecular Formula: C15H24O2
• Molecular Weight: 236.35
• UNII: 05X5L9F9XM
• DSSTox Substance ID: DTXSID30188628
• Nikkaji Number: J18.430F
• Wikidata: Q27236148
• Mol file: 35124-22-2.mol

Synonyms:Petasitolone;UNII-05X5L9F9XM;05X5L9F9XM;35124-22-2;2(1H)-Naphthalenone, 4a,5,6,7,8,8a-hexahydro-3-(1-hydroxy-1-methylethyl)-4a,5-dimethyl-, (4aR,5S,8aR)-;2(1H)-Naphthalenone, 4a,5,6,7,8,8a-hexahydro-3-(1-hydroxy-1-methylethyl)-4a,5-dimethyl-, (4ar-(4aalpha,5alpha,8aalpha))-;DTXSID30188628;CHEBI:173720;(4aR,5S,8aR)-3-(2-hydroxypropan-2-yl)-4a,5-dimethyl-1,5,6,7,8,8a-hexahydronaphthalen-2-one;Q27236148;2(1H)-NAPHTHALENONE, 4A,5,6,7,8,8A-HEXAHYDRO-3-(1-HYDROXY-1-METHYLETHYL)-4A,5-DIMETHYL-, (4AR-(4A.ALPHA.,5.ALPHA.,8A.ALPHA.))-

Chemical Property of Petasitolone

Chemical Property:

• PSA: 37.30000
• LogP: 3.09900
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 236.177630004
• Heavy Atom Count: 17
• Complexity: 367

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CCCC2C1(C=C(C(=O)C2)C(C)(C)O)C
• Isomeric SMILES: C[C@H]1CCC[C@H]2[C@@]1(C=C(C(=O)C2)C(C)(C)O)C

Technology Process of Petasitolone

There total 6 articles about Petasitolone 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: 80.0%

2-{(4a'S*,5'R*,8a'S*)-4a',5'-dimethyl-4a',5',6',7',8',8a'-hexahydro-1H'-spiro[1,3-dioxolane-2,2'-naphthalene]-3'-yl}propan-2-ol → petasitolone (35124-22-2,94063-55-5)

Guidance literature:

With hydrogenchloride; In dichloromethane; water; for 1h; Reflux; Inert atmosphere;

DOI:10.1055/s-0029-1218150

Reference yield: 79.0%

8β-hydroxy-2-(2-hydroxy-2-propyl)-8β,8a4B-dimethyl-3,4,4AΒ,5,6,7,8,8A-octahydronaphtalene (94013-99-7) → petasitolone (35124-22-2,94063-55-5)

Guidance literature:

With jones reagent; In acetone; at 0 ℃; for 0.166667h;

Reference yield:

2-carbomethoxy-8β,8aΒ-dimethyl-3,4,4aβ,5,6,7,8,8a-octahydronaphtalene → petasitolone (35124-22-2,94063-55-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 61 percent / SeO₂, / acetic acid / 49 h / reflux

2: 93 percent / diethyl ether; tetrahydrofuran / -78 °C

3: 79 percent / Jones reagent / acetone / 0.17 h / 0 °C

With selenium(IV) oxide; jones reagent; In tetrahydrofuran; diethyl ether; acetic acid; acetone;

upstream raw materials:

Fukinon

8β-hydroxy-2-(2-hydroxy-2-propyl)-8β,8a4B-dimethyl-3,4,4AΒ,5,6,7,8,8A-octahydronaphtalene

Downstream raw materials:

Fukinon

7β-Eremophilan-8-on

Eremophilan