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

• ChemBase ID: 302913
• Molecular Formular: C51H42O3Pd2
• Molecular Mass: 915.71738
• Monoisotopic Mass: 914.1203672
• SMILES: c1ccc(cc1)/C=C/C(=O)/C=C/c1ccccc1.c1ccc(cc1)/C=C/C(=O)/C=C\c1ccccc1.c1ccc(cc1)/C=C/C(=O)/C=C\c1ccccc1.[Pd].[Pd]
• Canonical SMILES: O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C\c1ccccc1)/C=C/c1ccccc1.O=C(/C=C\c1ccccc1)/C=C/c1ccccc1.[Pd].[Pd]
• InChI: InChI=1S/3C17H14O.2Pd/c3*18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16;;/h3*1-14H;;/b13-11+,14-12+;2*13-11-,14-12+
• InChIKey: CYPYTURSJDMMMP-WDSUVSFASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one bis((1Z,4E)-1,5-diphenylpenta-1,4-dien-3-one) dipalladium
• IUPAC Traditional name: tris(dibenzylideneacetone) dipalladium
• Synonyms: Bis[tris(dibenzylideneacetone)palladium(0)]; Pd2(dba)3; Tris(dibenzylideneacetone)dipalladium(0); 三(二亚苄基丙酮)二钯(0)

Database IDs

• CAS Number: 51364-51-3
• MDL Number: MFCD00013310

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: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Soluble in chlorinated solvents
• Apperance: Powder
• Melting Point: 152-155°C

Safety Information

• Storage Warning: Air & Moisture Sensitive
• TSCA Listed: 否

Product Information

• Purity: Pd 21.5% min

REFERENCES

• Stable source of phosphine-free Pd(0), useful in a variety of coupling reactions. Literature references to the use of either "Pd(dba)₂"or "Pd₂(dba)₃" can normally be regarded as interchangeable since the catalyst is of somewhat variable composition depending on the exact method of preparation.
• For use in the coupling of aryl- or vinyltin reagents with allyl halides, see: J. Am. Chem. Soc., 105, 7173 (1983). For Suzuki coupling of boronic acids with carbapenem triflates, see: Tetrahedron Lett., 34, 3211 (1993).
• Catalyzes the reduction of terminal allylic acetates or carbonates to 1-alkenes, with virtually complete regioselectivity: Synthesis, 623 (1986).
• Catalyzes the hydroxycarbonylation of aryl and vinyl halides or triflates by lithium formate, to give carboxylic acids: Org. Lett., 5, 4269 (2003).
• In the presence of allyl bromide, catalyzes the coupling of terminal alkynes to symmetrical diynes under phase-transfer conditions. The reaction is thought to involve a π-allyl Pd intermediate: Tetrahedron, 52, 1337 (1996).
• In the presence of a chelating phosphine ligand and NaO-t-Bu, bromopyridines can be aminated: J. Org. Chem., 61, 7240 (1996):
  
• Catalyst for Stille and Heck coupling reactions in supercritical CO₂, in combination with, e.g. Tris[3,5-bis(trifluoromethyl)phenyl]phosphine, L06941: Chem. Commun., 1397 (1998).