67279-69-0

Basic information

• Product Name: 2(3H)-Furanone, dihydro-5-(iodomethyl)-4-phenyl-, (4R,5S)-rel-
• CAS NO: 67279-69-0
• Molecular Formula: C11H11IO2
• Molecular Weight: 302.112
• Mol File: 67279-69-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2(3H)-Furanone, dihydro-5-(iodomethyl)-4-phenyl-, (4R,5S)-rel-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(3H)-Furanone, dihydro-5-(iodomethyl)-4-phenyl-, (4R,5S)-rel-(67279-69-0)
• EPA Substance Registry System: 2(3H)-Furanone, dihydro-5-(iodomethyl)-4-phenyl-, (4R,5S)-rel-(67279-69-0)

Safety Data

• Hazardous Substances Data: 67279-69-0(Hazardous Substances Data)

Upstream product

• 104-54-1 3-Phenylpropenol 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 5703-57-1 3-phenylpent-4-enoic acid 

Downstream Products

• 950838-18-3 (4S,5R)-5-(hydroxymethyl)-4-phenyldihydrofuran-2(3H)-one 
• 1423026-43-0 (R)-methyl 3-((S)-oxiran-2-yl)-3-phenylpropanoate 
• 112423-41-3 cis-5-Methyl-4-phenyl-4,5-dihydro-2(3H)-furanone 
• 92927-63-4 (4R^*, 5S^*)-dihydro-5-methyl-4-phenyl-2(3H)-furanone 
• 112654-28-1 2-Allyl-2-[2-((2S,3R)-5-oxo-3-phenyl-tetrahydro-furan-2-yl)-1-phenyl-ethyl]-malononitrile 

Relevant articles and documents

Optically pure γ-butyrolactones and epoxy esters via two stereocentered HKR of 3-substituted epoxy esters: A formal synthesis of (-)-paroxetine, Ro 67-8867 and (+)-eldanolide

The HKR of racemic anti- or syn-3-substituted epoxy esters catalyzed by a Co(iii)salen complex provides ready access to the corresponding enantioenriched 3,4-disubstituted γ-butyrolactones and 3-substituted epoxy esters. This strategy has been successfully employed in the formal synthesis of biologically active 3,4-disubstituted piperidine derivatives, (-)-paroxetine and Ro 67-8867 and a natural product, (+)-eldanolide.

Stereocontrolled iodolactonization of acyclic olefinic amides

Acyclic olefinic amides were iodolactonized in the mixed solvent of CH3CN and H2O (90:10, v/v) under reflux to give products with trans configuration of the newly formed iodomethyl to the inherent alkyl group in high yield.

Synthesis of 4-Penten-4-olides (γ-Methylene-γ-butyrolactones) via 4-Pentenoic Acids

4-Penten-4-olides (γ-Methylene-γ-butyrolactones) 7 are easily accessible starting from allylic alcohols 1, which on ortho ester Claisen rearrangement and hydrolytic work-up furnish 4-pentenoic acids 5.The latter on iodolactonization and hydrogen iodide elimination by means of 1,8-diazabicycloundec-7-ene (DBU) furnish 7, in good over-all yield and with variable substitution patterns. - Iodolactonization under kinetic control shows moderate 1,2- or 1,3-asymmetric induction (3:1 and ca. 2:1, respectively).The composition of the iodolactone mixtures 6 as well as the individual relative configurations are deduced from 1H and 13C NMR data. - Similary, the spirobipentenolide 13 is obtained starting from diethyl diallylmalonate (9) via 11 resulting from ester iodocyclization.