(4E)-1,5-diphenylpenta-1,4-dien-3-one

• ChemBase ID: 78682
• Molecular Formular: C17H14O
• Molecular Mass: 234.29246
• Monoisotopic Mass: 234.10446507
• SMILES: O=C(/C=C/c1ccccc1)/C=C/c1ccccc1
• Canonical SMILES: O=C(/C=C/c1ccccc1)/C=C/c1ccccc1
• InChI: InChI=1S/C17H14O/c18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16/h1-14H
• InChIKey: WMKGGPCROCCUDY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4E)-1,5-diphenylpenta-1,4-dien-3-one; (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; 1,5-diphenylpenta-1,4-dien-3-one
• IUPAC Traditional name: (4E)-1,5-diphenylpenta-1,4-dien-3-one; dibenzylideneacetone
• Synonyms: DISTYRYL KETONE; DIBENZAL ACETONE; (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; Dibenzalacetone; Dibenzylideneacetone; 1,5-Diphenyl-1,4-pentadien-3-one; trans,trans-1,5-Diphenyl-1,4-pentadien-3-one; trans,trans-Dibenzylideneacetone; Dibenzylideneacetone; 1,5-Diphenylpenta-1,4-dien-3-one; (E,E)-1,5-Diphenyl-1,4-pentadien-3-one; 1,5-二苯-1,4-戊二烯-3-酮; 反,反-二亚苄基丙酮; 联甲基苯乙烯酮; 反式,反式-二亚苄基丙酮

Database IDs

• CAS Number: 35225-79-7; 538-58-9
• EC Number: 208-697-5
• MDL Number: MFCD00004790
• Beilstein Number: 608434
• Merck Index: 143006
• PubChem SID: 24854806; 24867016; 162043445
• PubChem CID: 1549622; 640180
• Chemspider ID: 1266463
• Wikipedia Title: Dibenzylideneacetone

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 4.825144
• LogD (pH = 7.4): 4.825144
• Log P: 4.825144
• Molar Refractivity: 77.0272 cm^3
• Polarizability: 28.964622 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Insoluble in water
• Apperance: Yellow solid
• Melting Point: *Aldrich 110-111 oC (trans,trans isomer) ; *Merck 60 °C (cis,trans isomer); 104-107 °C(lit.); 107-113 °C; 112-114°C
• Boiling Point: 130 °C (cis,cis isomer) *Merck

Safety Information

• Storage Warning: Irritant
• German water hazard class: 3
• TSCA Listed: 是
• Main Hazard: Irritant
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (HPLC); 95+%; 97%; 98%; 98+%
• Linear Formula: C6H5CH=CHCOCH=CHC6H5

DETAILS

Sigma Aldrich - 246425

Packaging
10, 50 g in poly bottle
Application
Reactant involved in:
• Nazarov-like cyclization1
• Transfer hydrogenation2
• Lewis acid mediated condensation3
• Hetero-Diels-Alder reactions4
• Asymmetric 1,4-addition reactions5
• Michael addition reactions6

Sigma Aldrich - 43143

Other Notes
This reactive dienone readily forms carbo- or heterocyclic compounds with many nucleophiles.; Dibenzylideneacetone forms a stable zero-valent, neutral complex with palladium(0), Pd(dba)27; Preparation of Pd2(dba)3(solvent) complexes8; These palladium(0)-dibenzylideneacetone complexes are important catalysts9;
Packaging
10 g in glass bottle
Application
Reactant involved in:
• Nazarov-like cyclization1
• Transfer hydrogenation2
• Lewis acid mediated condensation3
• Hetero-Diels-Alder reactions4
• Asymmetric 1,4-addition reactions5
• Michael addition reactions6

REFERENCES

• Reactive dienone; ligand for palladium, see Tris(dibenzylideneacetone)dipalladium(0), 12760.