77341-51-6

Basic information

• Product Name: (+/-)-4-benzoyloxy-2-cyclopentenone
• Synonyms: (+/-)-4-benzoyloxy-2-cyclopentenone
• CAS NO: 77341-51-6
• Molecular Weight: 202.21
• Mol File: 77341-51-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (+/-)-4-benzoyloxy-2-cyclopentenone(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-4-benzoyloxy-2-cyclopentenone(77341-51-6)
• EPA Substance Registry System: (+/-)-4-benzoyloxy-2-cyclopentenone(77341-51-6)

Safety Data

• Hazardous Substances Data: 77341-51-6(Hazardous Substances Data)

Upstream product

• 59995-47-0 4-Hydroxycyclopent-2-enone 
• 93-97-0 benzoic acid anhydride 
• 63603-17-8 (-)-2-cyclopenten-1(R),4(S)-diyl bis-N-mesyl-(S)-phenylalaninate 
• 77300-17-5 dl-cis-4-tetrahydropyranoxy-2-cyclopentenyl benzoate 
• 61305-37-1 4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enone 
• 29783-26-4 cis-4-cyclopentene-1,3-diol 
• 98-88-4 benzoyl chloride 
• 61305-24-6 dl-cis-4-hydroxy-2-cyclopentenyl benzoate 
• 37517-41-2 (+/-)-cis-4-(2'R*-tetrahydropyranyloxy)-2-cyclopentenol 

Downstream Products

• 329363-21-5 (+/-)-ethyl (E)-4-t-butyldiphenylsiloxy-2-cyclopentenylideneacetate 
• 329363-20-4 ethyl (E)-4-oxo-2-cyclopentenylideneacetate 
• 329363-13-5 ethyl (Z)-4-oxo-2-cyclopentenylideneacetate 

Relevant articles and documents

Switchable selectivity in Pd-catalyzed [3 + 2] annulations of γ-oxy-2-cycloalkenones with 3-oxoglutarates: C-C/C-C vs C-C/O-C bond formation

Two complementary [3 + 2] annulation protocols between 3-oxoglutarates and cyclic γ-oxy-2-cycloalkenones, simply differing on the reaction temperature, are disclosed. These domino transformations allow C-C/O-C or C-C/C-C [3 + 2] annulations at will, via an intermolecular Pd-catalyzed C-allylation/intramolecular O- or C-1,4-addition sequence, respectively. In particular, exploiting the reversibility of the O-1,4-addition step, in combination with the irreversible C-1,4-addition/decarboxylation path, the intramolecular conjugate addition step could be diverted from the kinetic (O-alkylation) to the thermodynamic path (C-alkylation) thanks to a simple temperature increase. Crucial for the success of this bis-nucleophile/bis-electrophile [3 + 2] annulation is its well-defined step chronology in combination with the total chemoselectivity of the former step. This [3 + 2] C-C/O-C bond forming annulation protocol could be also extended to 1,3,5-triketones as well as 1,3-bis-sulfonylpropan-2-one bis-nucleophiles.

4-Hydroxycyclopent-2-en-1-one and derivatives as chiral synthetic equivalents of cyclopentadienone in asymmetric Diels-Alder reactions

Endo-tricyclodecadienone 8a and related annelated-cyclopentenones (8b, 20, 21a-c and 22) are synthesized in good chemical yield by a Diels-Alder reaction of 4-hydroxycyclo-pent-2-en-1-one 12a and derivatives 12b-h with an appropriate diene. These additions are considerably accelerated by Lewis catalysts, high pressure and by using water as solvent. Due to opposing steric and electronic effects the diastereofacial selectivity of the asymmetric cycloadditions is moderate. By carefully choosing the substrate and reaction conditions an acceptable π-facial selectivity can be achieved.