PETASIN

Base Information

• Chemical Name: PETASIN
• CAS No.: 26577-85-5
• Molecular Formula: C20H28 O3
• Molecular Weight: 316.441
• Mol file: 26577-85-5.mol

Synonyms:2-Butenoicacid, 2-methyl-,1,2,3,4,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-6-oxo-2-naphthalenylester, [1R-[1a,2b(Z),7b,8aa]]-; Eremophila-9,11-dien-8-one, 3a-hydroxy-, 2-methylcrotonate, (Z)- (8CI); Petasin(6CI,7CI); Crotonic acid, 2-methyl-, ester with 3a-hydroxy-eremophila-9,11-dien-8-one, (Z)- (8CI);(+)-Petasin; Petaforce

Chemical Property of PETASIN

Chemical Property:

• Vapor Pressure: 2.68E-07mmHg at 25°C
• Melting Point: 66-70℃
• Boiling Point: 421.1°Cat760mmHg
• Flash Point: 181.6°C
• PSA: 43.37000
• Density: 1.04g/cm³
• LogP: 4.39210

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of PETASIN

There total 9 articles about PETASIN 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: 69.0%

2-methylbut-2-enoic acid (1R,2R,7S,8aR)-7-(1-hydroxy-1-methylethyl)-1,8a-dimethyl-6-oxo-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl ester (164414-38-4) → Petasin (26577-85-5)

Guidance literature:

With trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1055/s-1997-1492

Reference yield: 17.0%

2-methylbut-2-enoic acid (1R,2R,7S,8aR)-7-(1-hydroxy-1-methylethyl)-1,8a-dimethyl-6-oxo-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl ester (164414-38-4) → Isopetasin (469-26-1) + Petasin (26577-85-5)

Guidance literature:

With trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1016/0040-4039(95)00475-R

Reference yield:

Angelic acid (565-63-9) → Petasin (26577-85-5)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / toluene / 2 h / Ambient temperature

2: Et₃N / toluene / 24 h / 80 °C

3: 69 percent / (CF₃SO₂)O, i-Pr₂NEt / CH₂Cl₂ / 1 h / -78 °C

With trifluoromethylsulfonic anhydride; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene;

DOI:10.1055/s-1997-1492

upstream raw materials:

2-methylbut-2-enoic acid (1R,2R,7S,8aR)-7-(1-hydroxy-1-methylethyl)-1,8a-dimethyl-6-oxo-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl ester

Angelic acid

(2Z)-2-methyl-2-butenoic 2,4,6-trichlorobenzoic anhydride

(4aR,5R,6R)-(+)-6-(tert-butyldimethylsiloxy)-4a,5-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one

Refernces

• 1、 Witschel, Matthias Christian,Bestmann, Hans Juergen. "Synthese der Pestwurzinhaltsstoffe (+)-Petasin und (+)-Isopetasin". . p. 3325 - 3328. Retrieved 2007/10/02.