Sesquirosefuran

Base Information

• Chemical Name: Sesquirosefuran
• CAS No.: 39007-93-7
• Molecular Formula: C15H22O
• Molecular Weight: 218.33
• DSSTox Substance ID: DTXSID401316650
• Nikkaji Number: J18.507H
• Wikidata: Q67880092
• Mol file: 39007-93-7.mol

Synonyms:Sesquirosefuran;Sesquirose furan;39007-93-7;2-[(2E)-3,7-dimethylocta-2,6-dienyl]-3-methylfuran;CKUQXDUZAWSPOV-MDWZMJQESA-N;DTXSID401316650;AKOS015906767;Furan, 2-(3,7-dimethyl-2,6-octadienyl)-3-methyl-;Q67880092;2-[(2E)-3,7-Dimethyl-2,6-octadienyl]-3-methylfuran;2-[(2E)-3,7-Dimethyl-2,6-octadienyl]-3-methylfuran #

Chemical Property of Sesquirosefuran

Chemical Property:

• Boiling Point: 310.4±21.0 °C(Predicted)
• PSA: 13.14000
• Density: 0.908±0.06 g/cm3(Predicted)
• LogP: 4.82320
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 218.167065321
• Heavy Atom Count: 16
• Complexity: 259

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(OC=C1)CC=C(C)CCC=C(C)C
• Isomeric SMILES: CC1=C(OC=C1)C/C=C(\C)/CCC=C(C)C

Technology Process of Sesquirosefuran

There total 20 articles about Sesquirosefuran 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: 85.0%

5-((E)-3,7-Dimethyl-octa-2,6-dienyl)-4-methyl-5H-furan-2-one (66641-64-3) → sesquirosefuran (39007-93-7)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at -78 - -5 ℃; for 3h;

DOI:10.1002/anie.200352180

Reference yield: 66.0%

3,7,11-trimethyl-4-hydroxy-2,6,10-trienenitrile (93040-86-9) → sesquirosefuran (39007-93-7)

Guidance literature:

With hydrogenchloride; hexane; diisobutylaluminium hydride; In diethyl ether; 1) 0 deg C, 1 h, 2) 10 deg C, several h;

DOI:10.1021/ja00337a042

Reference yield:

4-methyl-2-(triisopropyl)silyloxy-furan (203131-19-5) → sesquirosefuran (39007-93-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sec-BuLi; TMEDA / cyclohexane; tetrahydrofuran / 2 h / 0 °C

1.2: cyclohexane; tetrahydrofuran / 3 h / 0 °C

2.1: TFA / diethyl ether / 1 h / 25 °C

3.1: DIBAL-H / tetrahydrofuran / 3 h / -78 - -5 °C

With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; diisobutylaluminium hydride; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; cyclohexane;

DOI:10.1002/chem.200401311

upstream raw materials:

trans-geranyl bromide

(3-furylmethyl)magnesium bromide

(E)-3,7-dimethylocta-2,6-dien-1-yl diethyl phosphate

5-((E)-3,7-Dimethyl-octa-2,6-dienyl)-4-methyl-5H-furan-2-one