2-Methylpropionic acid [(3aR,4R,6R,11aR)-2,3,3a,4,5,6,7,11a-octahydro-6,10-dimethyl-3-methylene-2,7-dioxo-6,9-epoxycyclodeca[b]furan-4-yl] ester

Base Information

• Chemical Name: 2-Methylpropionic acid [(3aR,4R,6R,11aR)-2,3,3a,4,5,6,7,11a-octahydro-6,10-dimethyl-3-methylene-2,7-dioxo-6,9-epoxycyclodeca[b]furan-4-yl] ester
• CAS No.: 30412-87-4
• Molecular Formula: C₁₉H₂₂O₆
• Molecular Weight: 346.38
• Mol file: 30412-87-4.mol

Synonyms:10bH-Germacra-2,4,11(13)-trien-12-oicacid, 3,10-epoxy-6a,8a-dihydroxy-1-oxo-, 12,6-lactone,isobutyrate (8CI); Propanoic acid, 2-methyl-,2,3,3a,4,5,6,7,11a-octahydro-6,10-dimethyl-3-methylene-2,7-dioxo-6,9-epoxycyclodeca[b]furan-4-ylester, [3aR-(3aR*,4R*,6R*,11aR*)]-; 6,9-Epoxycyclodeca[b]furan, propanoic acidderiv.; Ciliarin

Chemical Property of 2-Methylpropionic acid [(3aR,4R,6R,11aR)-2,3,3a,4,5,6,7,11a-octahydro-6,10-dimethyl-3-methylene-2,7-dioxo-6,9-epoxycyclodeca[b]furan-4-yl] ester

Chemical Property:

• Melting Point: 150 °C
• Boiling Point: 546.5±50.0 °C(Predicted)
• PSA: 78.90000
• Density: 1.24±0.1 g/cm3(Predicted)
• LogP: 2.24390

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Methylpropionic acid [(3aR,4R,6R,11aR)-2,3,3a,4,5,6,7,11a-octahydro-6,10-dimethyl-3-methylene-2,7-dioxo-6,9-epoxycyclodeca[b]furan-4-yl] ester

There total 3 articles about 2-Methylpropionic acid [(3aR,4R,6R,11aR)-2,3,3a,4,5,6,7,11a-octahydro-6,10-dimethyl-3-methylene-2,7-dioxo-6,9-epoxycyclodeca[b]furan-4-yl] ester 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: 20.0%

dehydroanhydrotagitinin A (69440-09-1) → ciliarin (30412-87-4)

Guidance literature:

With o-toluenesulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 110 ℃; for 36h;

DOI:10.1021/jo01312a040

Reference yield:

orizabin (34367-14-1) → ciliarin (30412-87-4)

Guidance literature:

With jones reagent; In acetone; at 0 ℃; for 0.5h;

DOI:10.1021/jo01312a040

Reference yield:

Isobutyric acid (Z)-(1R,2R,4R,11R)-4-hydroxy-4,9-dimethyl-14-methylene-8,13-dioxo-6,12-dioxa-tricyclo[9.3.0.05,7]tetradec-9-en-2-yl ester (75197-73-8,75247-16-4) → ciliarin (30412-87-4)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. AcOH, Zn / 1 h / 100 °C

2: 8 mg / Jones reagent / acetone / 0.5 h / 0 °C

With jones reagent; acetic acid; zinc; In acetone;

DOI:10.1021/jo01312a040

upstream raw materials:

dehydroanhydrotagitinin A

orizabin

Isobutyric acid (Z)-(1R,2R,4R,11R)-4-hydroxy-4,9-dimethyl-14-methylene-8,13-dioxo-6,12-dioxa-tricyclo[9.3.0.0^5,7]tetradec-9-en-2-yl ester

Refernces