Foeniculin, (E)-

Base Information

• Chemical Name: Foeniculin, (E)-
• CAS No.: 78259-41-3
• Molecular Formula: C14H18O
• Molecular Weight: 202.296
• Hs Code.: 2909300000
• UNII: QO3391G00A
• DSSTox Substance ID: DTXSID20228921
• Nikkaji Number: J2.374.855J,J912.861A
• Wikidata: Q27287387
• Mol file: 78259-41-3.mol

Synonyms:Foeniculin, (E)-;(E)-Foeniculin;78259-41-3;Foeniculin;UNII-QO3391G00A;QO3391G00A;1-(3-methylbut-2-enoxy)-4-[(E)-prop-1-enyl]benzene;1-(3-Methyl-2-butenoxy)-4-(1-propenyl)benzene;FOENICULIN (ETHER);FOENICULIN [USP-RS];DTXSID20228921;JGELFJUQMIUNOO-SNAWJCMRSA-N;1-(3-Methyl-2-butenyloxy)-4-(1-propenyl)benzene;Benzene, 1-(3-methyl-2-butenoxy)-4-(1-propenyl)-;Q27287387;1-[(3-Methyl-2-butenyl)oxy]-4-[(1E)-1-propenyl]benzene #;BENZENE, 1-((3-METHYL-2-BUTENYL)OXY)-4-(1E)-1-PROPENYL-;BENZENE, 1-((3-METHYL-2-BUTEN-1-YL)OXY)-4-(1E)-1-PROPEN-1-YL-;BENZENE, 1-((3-METHYL-2-BUTENYL)OXY)-4-(1-PROPENYL)-, (E)-

Chemical Property of Foeniculin, (E)-

Chemical Property:

• Boiling Point: 313.7±11.0 °C(Predicted)
• PSA: 9.23000
• Density: 0.945±0.06 g/cm3(Predicted)
• LogP: 4.06470
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 202.135765193
• Heavy Atom Count: 15
• Complexity: 216

Purity/Quality:

99%, ^*data from raw suppliers

Foeniculin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC1=CC=C(C=C1)OCC=C(C)C
• Isomeric SMILES: C/C=C/C1=CC=C(C=C1)OCC=C(C)C
• Uses: Foeniculin is a compound within Illicium verum essential oil, which is also known as Star Anise.

Technology Process of Foeniculin, (E)-

There total 7 articles about Foeniculin, (E)- 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: 79.0%

(E)-1-(4-hydroxyphenyl)propene (20649-39-2) + prenyl bromide (870-63-3) → trans-foeniculin (78259-41-3)

Guidance literature:

With potassium carbonate; In acetone; for 12h; Heating;

DOI:10.1039/P19810000897

Reference yield: 71.0%

threo-2-diphenylphosphinoyl-1-<4-(3-methylbut-2-enyloxy)>phenylpropan-1-ol (89084-32-2,115693-83-9,115693-84-0) → trans-foeniculin (78259-41-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)88420-8

Reference yield:

methyl 4-((3-methylbut-2-en-1-yl)oxy)benzoate (34593-50-5) → trans-foeniculin (78259-41-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) BuLi

2: 74 percent / sodium borohydride

3: 71 percent / sodium hydride / dimethylformamide / 0.5 h / 50 °C

With sodium tetrahydroborate; n-butyllithium; sodium hydride; In N,N-dimethyl-formamide;

upstream raw materials:

(E)-1-(4-hydroxyphenyl)propene

prenyl bromide

threo-2-diphenylphosphinoyl-1-<4-(3-methylbut-2-enyloxy)>phenylpropan-1-ol

methyl 4-((3-methylbut-2-en-1-yl)oxy)benzoate

Downstream raw materials:

5-prop-1-enyl-2,3,3-trimethyl-2,3-dihydrobenzofuran

anisoxide

2-(1,2-dimethylprop-2-enyl)-4-prop-1-enylphenol

2-(1,1-dimethylprop-2-enyl)-4-prop-1-enylphenol

Refernces

• 1、 Buss, Antony D.,Mason, Ralph,Warren, Stuart. "TRANS ALKENES BY STEREOSELECTIVE REDUCTION OF α-Ph2PO KETONES: E-ISOSAFFROLE, E-ANETHOLE, AND FENICULIN". . p. 5293 - 5296. Retrieved 2007/10/02.