82416-05-5

Basic information

• Product Name: 2,6-bis(phenylselenyl)bicyclo<3.3.0>octane-3,7-dione-2,4,6,8-tetracarboxylate
• CAS NO: 82416-05-5
• Molecular Weight: 680.428
• Mol File: 82416-05-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2,6-bis(phenylselenyl)bicyclo<3.3.0>octane-3,7-dione-2,4,6,8-tetracarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-bis(phenylselenyl)bicyclo<3.3.0>octane-3,7-dione-2,4,6,8-tetracarboxylate(82416-05-5)
• EPA Substance Registry System: 2,6-bis(phenylselenyl)bicyclo<3.3.0>octane-3,7-dione-2,4,6,8-tetracarboxylate(82416-05-5)

Safety Data

• Hazardous Substances Data: 82416-05-5(Hazardous Substances Data)

Upstream product

• 1666-13-3 diphenyl diselenide 
• 82416-02-2 C₁₆H₁₆O₁₀^(2-)*2Na⁽¹⁺⁾ 
• 1830-54-2 3-oxopentanedioic acid dimethyl ester 

Relevant articles and documents

REACTION OF DIMETHYL SODIO-3-KETOGLUTARATE WITH GLYOXAL AND SUBSTITUTED GLYOXALS; FIRST EXPEDITIOUS PREPARATION OF BICYCLOOCTANE-3,7-DIONE; SYNTHESIS AND CRYSTAL STRUCTURE OF 5,7-DIHYDROXY-4-METHOXYCARBONYL-3-PHENYL-1-INDANONE

A simple and efficient two-step preparation of bicyclooctane-3,7-dione starting from the sodium enolate of dimethyl 3-ketoglutarate and glyoxal is described.This is an unprecedented case in which a condensation reaction of glyoxal is more successful under vigorous conditions (refluxing methanol) than under much milder ones (buffered water at ambient temperature).The major product (after hydrolysis-decarboxylation) from the analogous sequence with phenylglyoxal is 5,7-dihydroxy-4-methoxycarbonyl-3-phenyl-1-indanone, the result of a Dieckmann reaction in addition to the Michael and aldol reactions.Only the latter two occur in aqueous buffers, where the product after hydrolysis-decarboxylation is 1-phenylbicyclooctane-3,7-dione.The X-ray crystal structure of the indanone reveals a novel hydrogen bonding phenomenon.