2-Acetyl-3-(prop-2-en-1-yl)naphthalene-1,4-dione

Base Information

• Chemical Name: 2-Acetyl-3-(prop-2-en-1-yl)naphthalene-1,4-dione
• CAS No.: 87976-14-5
• Molecular Formula: C15H12O3
• DSSTox Substance ID: DTXSID20519588
• Nikkaji Number: J259.038G
• Wikidata: Q82382883
• Mol file: 87976-14-5.mol

Synonyms:87976-14-5;2-Acetyl-3-(prop-2-en-1-yl)naphthalene-1,4-dione;DTXSID20519588

Chemical Property of 2-Acetyl-3-(prop-2-en-1-yl)naphthalene-1,4-dione

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 240.078644241
• Heavy Atom Count: 18
• Complexity: 456

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)C1=C(C(=O)C2=CC=CC=C2C1=O)CC=C

Technology Process of 2-Acetyl-3-(prop-2-en-1-yl)naphthalene-1,4-dione

There total 7 articles about 2-Acetyl-3-(prop-2-en-1-yl)naphthalene-1,4-dione 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: 41.0%

2-acetyl-1,4-naphthoquinone (5813-57-0) + trimethyl(allyl)stannane (762-73-2) → 2-acetylnaphthalene-1,4-diol (40420-48-2) + 3-allyl-2-hydroxy-1,4-naphthoquinone (40815-76-7) + 2-acetyl-3-prop-2-enyl-1,4-naphthoquinone (87976-14-5) + 2-acetyl-3-allyl-2,3-epoxy-2,3-dihydro-1,4-naphthoquinone + 3a-acetyl-2-trimethylstannyl-2,3,3a,4,9,9a-hexahydro-1H-cyclopentanaphthalene-4,9-dione (127889-59-2)

Guidance literature:

In dichloromethane; byproducts: 5-acetyl-2H-benzo{h}chromene-6-ol; dissolved acylquinone and allylstannane stood for 20 h under Ar; concd.; column chromy. (silica gel); eluted (hexane/ether); 5-acetyl-2H-benzo(h)chromene-6-ol was obtained with a yield of 3%; NMR; IR; mass spectra; elem. anal.;

DOI:10.1246/bcsj.62.3877

Reference yield: 35.0%

2-acetyl-1,4-naphthoquinone (5813-57-0) + allyltributylstanane (24850-33-7) → 3a-acetyl-2-tributylstannyl-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta{b}naphthalene-4,9-dione (127869-77-6) + 2-acetylnaphthalene-1,4-diol (40420-48-2) + 3-allyl-2-hydroxy-1,4-naphthoquinone (40815-76-7) + 2-acetyl-3-prop-2-enyl-1,4-naphthoquinone (87976-14-5) + 2-acetyl-3-allyl-2,3-epoxy-2,3-dihydro-1,4-naphthoquinone

Guidance literature:

In benzene; byproducts: 5-acetyl-2H-benzo{h}chromene-6-ol; dissolved acylquinone and allylstannane stood for 20 h under Ar; concd.; column chromy. (silica gel); eluted (hexane/ether); 5-acetyl-2H-benzo(h)chromene-6-ol was obtained with a yield of 2%; NMR; IR; mass spectra; UV/VIS; elem. anal.;

DOI:10.1246/bcsj.62.3877

Reference yield: 30.0%

2-acetyl-1,4-naphthoquinone (5813-57-0) + allyltributylstanane (24850-33-7) → 2-acetylnaphthalene-1,4-diol (40420-48-2) + 3-allyl-2-hydroxy-1,4-naphthoquinone (40815-76-7) + 2-acetyl-3-prop-2-enyl-1,4-naphthoquinone (87976-14-5) + 2-acetyl-3-allyl-2,3-epoxy-2,3-dihydro-1,4-naphthoquinone

Guidance literature:

In acetonitrile; for 1h; Further byproducts given;

DOI:10.1246/bcsj.62.3877

upstream raw materials:

2-acetyl-1,4-naphthoquinone

allyltributylstanane

trimethyl(allyl)stannane