24292-29-3

Basic information

• Product Name: (1R,6R)-5β-Hydroxy-3-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one
• Synonyms: Epoxydone;Phyllosinol;(1R,5R,6R)-5-Hydroxy-3-(hydroxymethyl)-7-oxabicyclo[4.1.0]hepta-3-ene-2-one;(1R,6R)-5β-Hydroxy-3-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one;(1R,6R)-5β-Hydroxy-3-hydroxymethyl-7-oxabicyclo[4.1.0]hept-3-en-2-one;(1α,6α)-3-(Hydroxymethyl)-5β-hydroxy-7-oxabicyclo[4.1.0]hepta-3-ene-2-one
• CAS NO: 24292-29-3
• Molecular Formula: C₇H₈O₄
• Molecular Weight: 156.13602
• Mol File: 24292-29-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 40-45 °C
• Boiling Point: 445.2°C at 760 mmHg
• Flash Point: 196.2°C
• Appearance: /
• Density: 1.567g/cm³
• Vapor Pressure: 8.53E-10mmHg at 25°C
• Refractive Index: 1.617
• PKA: 12.66±0.40(Predicted)
• CAS DataBase Reference: (1R,6R)-5β-Hydroxy-3-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,6R)-5β-Hydroxy-3-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one(24292-29-3)
• EPA Substance Registry System: (1R,6R)-5β-Hydroxy-3-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one(24292-29-3)

Safety Data

• Hazardous Substances Data: 24292-29-3(Hazardous Substances Data)

Usage

General Description

(1R,6R)-5β-Hydroxy-3-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one, also known as 7-oxabicyclo[4.1.0]hept-3-en-2-one, is a chemical compound with a bicyclic structure. It contains a hydroxy group and a hydroxymethyl group, making it a ketone and an alcohol simultaneously. (1R,6R)-5β-Hydroxy-3-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one has potential applications in organic synthesis and medicinal chemistry due to its unique structure and reactivity. It can be used as a building block for the synthesis of more complex molecules, or as a starting material for the development of pharmaceuticals. Additionally, its bicyclic structure may exhibit interesting biological activities that could be explored for various therapeutic purposes.

InChI:InChI=1/C7H8O4/c8-2-3-1-4(9)6-7(11-6)5(3)10/h1,4,6-9H,2H2/t4-,6-,7+/m1/s1

Upstream product

• 55164-61-9 (+/-)-(1α,5α,6α)-5-hydroxy-7-oxabicyclo<4.1.0>hept-3-en-2-one 
• 76596-36-6 Chloro-acetic acid (1S,2R,3S,4S,6R)-3-bromo-4-(2-chloro-acetoxymethyl)-5-oxo-7-oxa-bicyclo[4.1.0]hept-2-yl ester 

Downstream Products

• 76596-39-9 (4R,5S,6R)-4,5-Dihydroxy-2-hydroxymethyl-6-propylsulfanyl-cyclohex-2-enone 
• 32744-80-2 2-chloro-6-(hydroxymethyl)benzene-1,4-diol 

Relevant articles and documents

Synthesis of (+)-Epoxydon, (–)-Phyllostine, (–)-RKTS 33, and (–)-Parasitenone Featuring Selective Sulfonylation and Oxirane Ring Closure of Aldol Cyclization Products

Two new synthetic approaches to anhydrogabosines are developed from the polyoxygenated aldol cyclization intermediates, bearing different O-protecting groups, which were transformed to various gabosine-type cyclitols. Selective sulfonylation on the required hydroxyl group of the intermediates and the subsequent oxirane ring closure are employed as the key steps in both approaches, by which (+)-epoxydon, (–)-phyllostine, (–)-RKTS 33, and (–)-parasitenone were synthesized from δ-d-gluconolactone.

The synthesis of epi-epoxydon utilising the Baylis-Hillman reaction

(±)-epi-Epoxydon was synthesised by means of a triethylaluminium/tri-n-butylphosphine-catalysed Baylis-Hillman reaction between an O-protected epoxidised hydroxyquinol core and paraformaldehyde, constituting the first application of the Baylis-Hillman reaction to a highly functionalised β-substituted enone.

Stereospecific Synthesis of dl-Isoepoxydon, a New Metabolite of Importance to the Patulin Pathway

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