126402-10-6

Basic information

• Product Name: Bicyclo[3.2.1]oct-3-ene-2,8-dione, 3-hydroxy-6-methyl-7-phenyl-, (6-exo,7-endo)-
• CAS NO: 126402-10-6
• Molecular Formula: C15H14O3
• Molecular Weight: 242.274
• Mol File: 126402-10-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Bicyclo[3.2.1]oct-3-ene-2,8-dione, 3-hydroxy-6-methyl-7-phenyl-, (6-exo,7-endo)-(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[3.2.1]oct-3-ene-2,8-dione, 3-hydroxy-6-methyl-7-phenyl-, (6-exo,7-endo)-(126402-10-6)
• EPA Substance Registry System: Bicyclo[3.2.1]oct-3-ene-2,8-dione, 3-hydroxy-6-methyl-7-phenyl-, (6-exo,7-endo)-(126402-10-6)

Safety Data

• Hazardous Substances Data: 126402-10-6(Hazardous Substances Data)

Upstream product

• 637-50-3 1-phenylpropene 
• 29938-06-5 2-(Benzyloxy)-1,4-benzoquinone 
• 130642-21-6 2-(4-Methoxy-benzyloxy)-[1,4]benzoquinone 
• 873-66-5 1-propenylbenzene 
• 168648-80-4 N-[3-Benzyloxy-4-oxo-cyclohexa-2,5-dien-(E)-ylidene]-benzenesulfonamide 

Relevant articles and documents

Lewis acid-controlled regioselectivity in reactions of styrenyl systems with benzoquinone monoimides: New regioselective syntheses of substituted 2-aryl-2,3-dihydrobenzofurans, 2-aryl-2,3-dihydroindoles, and 2-arylindoles

Reactions of 4-(N-phenylsulfonyl)-2-alkoxy-1,4-benzoquinone monoimines 2-4 with electron-rich propenylbenzenes promoted by BF3 yield 7-alkoxy-2-aryl-3-methyl-5-[(N-phenylsulfonyl)amino]-2,3-dihydrobenzofurans 5-7 nearly exclusively, whereas promotion of the reactions by Ti4+ gives mixtures of the dihydrobenzofurans and their N-(phenylsulfonyl)-6-alkoxy-2-aryl-5-hydroxy-3-methyl-2,3-dihydroindole isomers 8-10, depending upon substituents present on the propenylbenzene. However, reactions promoted with excess Ti4+, as mixtures of TiCl4:Ti(OiPr)4, give the dihydroindoles as nearly the exclusive products. Evidence for a mechanism involving initial 5 + 2 cycloaddition of the Lewis acid-bound quinone monoimide with the propenylbenzene is found in reactions of styrenes 1f/g with monoimide 3 in which 7-aryl-3-hydroxy-6-methylbicyclo[3.2.1]oct-3-ene-2,8-diones 33 (5 + 2 adducts) are isolated. These reactions have been applied to stereoselective syntheses of pterocarpans bearing N-phenylsulfonyl groups, azapterocarpans and diazapterocarpans. In addition, DDQ oxidation of derivatives of several of the 2-aryl-2,3-dihydroindoles afford the corresponding 2-arylindoles in good yield. Finally, the experimental details of a general synthetic approach to 7-alkoxy-benzofuranoid neolignans, including (±)-licarin B and eupomatenoids-1 and -12 are reported.

Selective Control of the Various Cycloaddition Products from Reactions of Styrenes and 1,4-Benzoquinones: Optimization of the Formal 5 +2 Cycloadducts

7-Aryl-3-hydroxy-6-methylbicyclooct-3-ene-2,8-diones 4 and 8 are formed exclusively in Ti(IV)-catalyzed reactions of 2-((4-methoxybenzyl)oxy)-1,4-benzoquinones 5a/d with trans-β-methylstyrene and indene, resprectively.