3,3-Diallyl-2,4-pentanedione

Base Information

• Chemical Name: 3,3-Diallyl-2,4-pentanedione
• CAS No.: 3508-79-0
• Molecular Formula: C₁₁H₁₆O₂
• Molecular Weight: 180.247
• DSSTox Substance ID: DTXSID101286111
• Nikkaji Number: J444.919C
• Mol file: 3508-79-0.mol

Synonyms:3,3-Diallyl-2,4-pentanedione;3508-79-0;SCHEMBL6831466;DTXSID101286111;3,3-Di-2-propen-1-yl-2,4-pentanedione

Chemical Property of 3,3-Diallyl-2,4-pentanedione

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 180.115029749
• Heavy Atom Count: 13
• Complexity: 213

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)C(CC=C)(CC=C)C(=O)C

Technology Process of 3,3-Diallyl-2,4-pentanedione

There total 10 articles about 3,3-Diallyl-2,4-pentanedione 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: 89.0%

allyl methyl carbonate (35466-83-2) + acetylacetone (123-54-6,81235-32-7) → 3-allyl-2,4-pentanedione (3508-78-9) + 3,3-diallylpentane-2,4-dione (3508-79-0)

Guidance literature:

chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II); In 1,2-dichloro-ethane; at 90 ℃; for 6h;

DOI:10.1002/chem.200305340

Reference yield: 75.0%

3-chloroprop-1-ene (107-05-1) + acetylacetone (123-54-6,81235-32-7) → 3-allyl-2,4-pentanedione (3508-78-9) + 3,3-diallylpentane-2,4-dione (3508-79-0)

Guidance literature:

acetylacetone; With sodium butyrate; In acetonitrile; for 0.333333h; Microwave irradiation;

3-chloroprop-1-ene; In acetonitrile; for 2h; Microwave irradiation;

DOI:10.1134/S1070363216090255

Reference yield: 55.0%

allyl N-phenyliminobenzoate (85021-16-5) + acetylacetone (123-54-6,81235-32-7) → 3-allyl-2,4-pentanedione (3508-78-9) + 3,3-diallylpentane-2,4-dione (3508-79-0)

Guidance literature:

With 1,2-bis-(diphenylphosphino)ethane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In N,N-dimethyl-formamide; for 1h; Ambient temperature;

DOI:10.1246/bcsj.62.239

upstream raw materials:

acetylacetone

allyl alcohol

allyl bromide

allyl methyl carbonate

Downstream raw materials:

1-[1-Acetyl-3-bromomethyl-4-(toluene-4-sulfonylmethyl)-cyclopentyl]-ethanone

1,1-diacetyl-3-(3-ethoxycarbonyl-3-buten-1-yl)-4-p-toluenesulfonylmethyl-cyclopentane

1,1-diacetyl-3-(3-ethoxycarbonyl-3-buten-1-yl)-4-p-toluenesulfonylmethyl-cyclopentane

3-allyl-2,4-pentanedione

Refernces

• 1、 Llevot,Monney,Sehlinger,Behrens,Meier. "Highly efficient Tsuji-Trost allylation in water catalyzed by Pd-nanoparticles". supporting information. p. 5175 - 5178. Retrieved 2017/07/12.
• 2、 Monopoli, Antonio,Cotugno, Pietro,Zambonin, Carlo G.,Ciminale, Francesco,Nacci, Angelo. "Highly selective palladium-benzothiazole carbene-catalyzed allylation of active methylene compounds under neutral conditions". supporting information. p. 994 - 999. Retrieved 2015/08/19.