3-(4,8-Dimethylnona-2,4,6-trien-1-yl)furan

Base Information

• Chemical Name: 3-(4,8-Dimethylnona-2,4,6-trien-1-yl)furan
• CAS No.: 41060-02-0
• Molecular Formula: C15H20O
• Molecular Weight: 0
• DSSTox Substance ID: DTXSID30702025
• Wikidata: Q82633825,Q105242068,Q105242063,Q105242066
• Mol file: 41060-02-0.mol

Synonyms:DTXSID30702025;41060-02-0;3-(4,8-Dimethylnona-2,4,6-trien-1-yl)furan

Chemical Property of 3-(4,8-Dimethylnona-2,4,6-trien-1-yl)furan

Chemical Property:

• PSA: 13.14000
• LogP: 4.53680
• XLogP3: 5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 216.151415257
• Heavy Atom Count: 16
• Complexity: 271

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C=CC=C(C)C=CCC1=COC=C1

Technology Process of 3-(4,8-Dimethylnona-2,4,6-trien-1-yl)furan

There total 7 articles about 3-(4,8-Dimethylnona-2,4,6-trien-1-yl)furan 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: 83.0%

(E)-2-(3-methyl-1-butenyl)-1,3,2-benzodioxaborole + 3-((2E,4E)-5-Iodo-4-methyl-penta-2,4-dienyl)-furan (187335-24-6) → (2'E,4'E,6'E)-3-(4',8'-dimethylnona-2',4',6'-trienyl)furan (41060-02-0)

Guidance literature:

With potassium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; silver carbonate; In tetrahydrofuran; for 3.5h; Ambient temperature;

DOI:10.1016/S0040-4020(96)01190-8

Reference yield:

3-furylacetaldehyde (99948-48-8) → (2'E,4'E,6'E)-3-(4',8'-dimethylnona-2',4',6'-trienyl)furan (41060-02-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / benzene / 0.17 h / Ambient temperature

2: 80 percent / Dess-Martin periodinate / CH₂Cl₂ / 0.08 h / Ambient temperature

3: 1.) Ph₃P / 1) CH₂Cl₂, 0 deg C, 10 min; 2) CH₂Cl₂

4: 94 percent / LDA / tetrahydrofuran / 1) -78 deg C, 5 min; 2) 0 deg C, 10 min

5: 1.) methyl(tributylstannyl)magnesium, cuprous cyanide, 3.) I₂ / 1) THF, hexane, -20 deg C, 15 min; 2) THF, hexane, -20 deg C, 30 min; 3) THF, hexane, CH₂Cl₂, 0-5 deg C

6: 83 percent / silver carbonate, Pd(PPh₃)4, aq. KOH / tetrahydrofuran / 3.5 h / Ambient temperature

With potassium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; methylmagnesium tributylstannane; iodine; copper(l) cyanide; Dess-Martin periodane; triphenylphosphine; silver carbonate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1016/S0040-4020(96)01190-8

Reference yield:

(e)-4-(3-furyl)-2-butenal (187335-19-9) → (2'E,4'E,6'E)-3-(4',8'-dimethylnona-2',4',6'-trienyl)furan (41060-02-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) Ph₃P / 1) CH₂Cl₂, 0 deg C, 10 min; 2) CH₂Cl₂

2: 94 percent / LDA / tetrahydrofuran / 1) -78 deg C, 5 min; 2) 0 deg C, 10 min

3: 1.) methyl(tributylstannyl)magnesium, cuprous cyanide, 3.) I₂ / 1) THF, hexane, -20 deg C, 15 min; 2) THF, hexane, -20 deg C, 30 min; 3) THF, hexane, CH₂Cl₂, 0-5 deg C

4: 83 percent / silver carbonate, Pd(PPh₃)4, aq. KOH / tetrahydrofuran / 3.5 h / Ambient temperature

With potassium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; methylmagnesium tributylstannane; iodine; copper(l) cyanide; triphenylphosphine; silver carbonate; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/S0040-4020(96)01190-8

upstream raw materials:

3-((2E,4E)-5-Iodo-4-methyl-penta-2,4-dienyl)-furan

3-furylacetaldehyde

(e)-4-(3-furyl)-2-butenal

3-((E)-5,5-Dibromo-penta-2,4-dienyl)-furan