6935-56-4

Basic information

• Product Name: 6-iodo-7-phenylhexahydro-2H-3,5-methanocyclopenta[b]furan-2-one
• Synonyms: 3,5-Methano-2H-cyclopenta[b]furan-2-one, hexahydro-6-iodo-7-phenyl-
• CAS NO: 6935-56-4
• Molecular Formula: C₁₄H₁₃IO₂
• Molecular Weight: 340.1563
• Mol File: 6935-56-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 467.5°C at 760 mmHg
• Flash Point: 236.5°C
• Density: 1.77g/cm³
• Vapor Pressure: 6.48E-09mmHg at 25°C
• Refractive Index: 1.676
• CAS DataBase Reference: 6-iodo-7-phenylhexahydro-2H-3,5-methanocyclopenta[b]furan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-iodo-7-phenylhexahydro-2H-3,5-methanocyclopenta[b]furan-2-one(6935-56-4)
• EPA Substance Registry System: 6-iodo-7-phenylhexahydro-2H-3,5-methanocyclopenta[b]furan-2-one(6935-56-4)

Safety Data

• Hazardous Substances Data: 6935-56-4(Hazardous Substances Data)

Upstream product

• 140-10-3 cis-cinnamic acid 
• 542-92-7 cyclopenta-1,3-diene 
• 140-10-3 (E)-3-phenylacrylic acid 
• 102-92-1 Cinnamoyl chloride 

Downstream Products

• 81509-24-2 phenyl-3 endo bicyclo<2.2.1> heptene-5 carboxylate endo-2 de methyle 
• 81509-28-6 phenyl-3 endo bicyclo<2.2.1>heptane carbolactone 2-6 
• 81509-24-2 phenyl-3 exo bicyclo<2.2.1> heptene-5 carboxylate endo-2 de methyle 
• 81509-28-6 phenyl-3 exo bicyclo<2.2.1>heptane carbolactone 2-6 
• 6319-20-6 5-exo-carboxy-6-exo-phenylbicyclo<2.2.1>heptane 
• 6319-19-3 5-exo-carboxy-6-exo-phenylbicyclo<2.2.1>hept-2-ene 
• 6319-20-6 endo-2-carboxy-exo-3-phenylbicyclo<2.2.1>heptane 
• 112459-62-8 (4S,1'S,2'S,3'R,4'R)-3-[(3'-phenylbicyclo[2.2.1]hept-5'-ene-2'-yl)carbonyl]-4-iso-propyloxazolidin-2-one 
• 112459-62-8 (4S)-3-((3'R,4'S,5'S,6'R)-5'-phenylbicyclo<2.2.1>heptene-4'-carbonyl)-4-(1-methylethyl)-2-oxazolidinone 
• 6319-19-3 endo-5-carboxy-exo-6-phenylbicyclo<2.2.1>hept-2-ene 
• 6319-19-3 3-endo-phenylnorborn-5-ene-2-endo-ylcarboxylic acid 
• 86960-91-0 6-endo-hydroxy-3-phenylnortricycl-2-endo-2-ylcarboxylic acid γ-lactone 

Relevant articles and documents

SuperQuat 5,5-dimethyl-4-iso-propyloxazolidin-2-one as a mimic of Evans 4-tert-butyloxazolidin-2-one

The incorporation of a gem-dimethyl group at the 5-position of a chiral oxazolidinone biases the conformation of the adjacent C(4)-stereodirecting group such that the gem-dimethyl-4-iso-propyl combination mimics a C(4)-tert-butyl group, providing higher levels of stereocontrol than a simple 4-iso-propyloxazolidinone. The generality of this principle is demonstrated with applications in stereoselective enolate alkylations, kinetic resolutions, Diels-Alder cycloadditions and Pd-catalysed asymmetric acetalisation reactions. The Royal Society of Chemistry 2006.

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The synthesis, 1H and 13C NMR spectra of acids 1 to 4 and methyl esters 5 to 8 are described. Interaction of aromatic and polar groups in the cis acids must be steric in origin and not due to charge transfer complex or hydrogen bondi