78394-08-8

Basic information

• Product Name: (4bR,6R,8aR)-1,3,6,9,9-Pentamethyl-1,4b,5,6,7,8,8a,9-octahydro-10-oxa-1,3-diaza-phenanthrene-2,4-dione
• CAS NO: 78394-08-8
• Molecular Weight: 292.378
• Mol File: 78394-08-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (4bR,6R,8aR)-1,3,6,9,9-Pentamethyl-1,4b,5,6,7,8,8a,9-octahydro-10-oxa-1,3-diaza-phenanthrene-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (4bR,6R,8aR)-1,3,6,9,9-Pentamethyl-1,4b,5,6,7,8,8a,9-octahydro-10-oxa-1,3-diaza-phenanthrene-2,4-dione(78394-08-8)
• EPA Substance Registry System: (4bR,6R,8aR)-1,3,6,9,9-Pentamethyl-1,4b,5,6,7,8,8a,9-octahydro-10-oxa-1,3-diaza-phenanthrene-2,4-dione(78394-08-8)

Safety Data

• Hazardous Substances Data: 78394-08-8(Hazardous Substances Data)

Upstream product

• 769-42-6 1,3-dimethylbarbituric acid 
• 106-23-0 3,7-dimethyl-oct-6-enal 

Relevant articles and documents

Simple and Induced Diastereoselectivity in Intramolecular Hetero-Diels-Alder Reactions of 1-Oxa-1,3-butadienes. Experimental Data and Calculations

The simple and induced diastereoselectivity of the intramolecular hetero-Diels-Alder reaction of the alkylidene 1,3-dicarbonyl compounds 7a-e, obtained in situ by Knoevenagel condensation of the aldehydes 5a-e and dimethylbarbituric acid 6 was investigated experimentally and theoretically.In all examples the selectivity is very high; thus the domino reaction of 5a and 6 gives nearly exclusively the trans-fused tricyclic dihydropyran 8 (trans/cis = 98.8:1.2).In the similar reactions of the chiral aldehydes 5b-e and 6 the trans cycloadducts 28, 33, 36, and 41 are the main products out of four possible diasteremers.The induced diastereoselectivity for the reaction of 5b and 5e with 6 is > 99:1 and for the reaction of 5c and 5d with 6, 95.2:3.6 and 94.1:4.7, respectively.Semiempirical AM1 calculations have been used to locate the transition structures of the intramolecular hetero-Diels-Alder reaction of 7a.The results were employed to create new parameters for the MM2-type force-field to determine the transition structures of 7b-e.The obtained data were compared with the experimental results of the cycloadditions and showed an excellent agreement.