32384-16-0

Basic information

• Product Name: endo-3,5,10-Trioxatricyclo<5.2.1.0^2,6>dec-8-en-4-on
• Synonyms: endo-3,5,10-Trioxatricyclo<5.2.1.0^2,6>dec-8-en-4-on
• CAS NO: 32384-16-0
• Molecular Weight: 154.122
• Mol File: 32384-16-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: endo-3,5,10-Trioxatricyclo<5.2.1.0^2,6>dec-8-en-4-on(CAS DataBase Reference)
• NIST Chemistry Reference: endo-3,5,10-Trioxatricyclo<5.2.1.0^2,6>dec-8-en-4-on(32384-16-0)
• EPA Substance Registry System: endo-3,5,10-Trioxatricyclo<5.2.1.0^2,6>dec-8-en-4-on(32384-16-0)

Safety Data

• Hazardous Substances Data: 32384-16-0(Hazardous Substances Data)

Upstream product

• 110-00-9 furan 
• 872-36-6 vinylene carbonate 

Downstream Products

• 94294-12-9 cis, endo-7-oxabicyclo<2.2.1>hepta-2,3-diyl dibrosylate 
• 61825-76-1 (1α,2α,3β,6β)-6-bromo-4-cyclohexene-1,2,3-triol 
• 4381-96-8 (+/-)-tetra-O-acetylconduritol F 
• 109526-05-8 conduritol A tetraacetate 
• 50269-97-1 7-Oxabicyclo<2.2.1>hept-5-en-exo/endo-2,exo/endo-3-diol 

Relevant articles and documents

Synthesis of haloconduritols from an endo-cycloadduct of furan and vinylene carbonate

A method for preparing haloconduritols having a conduritol-A construction is described. A mixture of endo- and exo-cycloadduct derivatives prepared from the Diels-Alder reaction of furan and vinylene carbonate was converted into diacetate derivatives by hydrolysis (K2CO3/MeOH) followed by acetylation (Ac2O/pyridine). Boron trihalide (BBr3 or BCl3)-assisted ring-opening of the endo-diacetate in CH2Cl2 at -78°C gave (1α,2α,3β,6β)-6-halogeno-4-cyclohexene-1,2,3-triol 1,2-diacetate from which the corresponding triacetate was prepared by acetylation (AcCl). trans-Esterification of the triacetate (MeOH/HCl) afforded (1α,2α,3β,6β)-6-halogeno-4-cyclohexene-1,2,3-triol (X=Br or Cl). BF3-Assisted ring-opening of the endo-diacetate in CH2Cl2 gave (1α,2α,3β,6β)-6-chloro-4-cyclohexene-1,2,3-triol 1,2-diacetate by means of halogen exchange.