1644560-10-0

Basic information

• Product Name: (R)-9-(2-methoxyphenyl)-2,3,4,9-tetrahydro-1H-xanthen-1-one
• CAS NO: 1644560-10-0
• Molecular Weight: 306.361
• Mol File: 1644560-10-0.mol

Chemical Properties

• CAS DataBase Reference: (R)-9-(2-methoxyphenyl)-2,3,4,9-tetrahydro-1H-xanthen-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-9-(2-methoxyphenyl)-2,3,4,9-tetrahydro-1H-xanthen-1-one(1644560-10-0)
• EPA Substance Registry System: (R)-9-(2-methoxyphenyl)-2,3,4,9-tetrahydro-1H-xanthen-1-one(1644560-10-0)

Safety Data

• Hazardous Substances Data: 1644560-10-0(Hazardous Substances Data)

Upstream product

• 1644559-91-0 2-(hydroxy(2-methoxyphenyl)methyl)phenol 
• 504-02-9 1,3-cylohexanedione 

Relevant articles and documents

Enantio- and diastereoselective access to distant stereocenters embedded within tetrahydroxanthenes: Utilizing ortho-quinone methides as reactive intermediates in asymmetric bronsted acid catalysis

A protocol for the highly enantioselective synthesis of 9-substituted tetrahydroxanthenones by means of asymmetric Bronsted acid catalysis has been developed. A chiral binolbased N-triflyphosphoramide was found to promote the in situ generation of ortho-quinone methides and their subsequent reaction with 1,3-cyclohexanedione to provide the desired products with excellent enantioselectivities. In addition, a highly enantio- and diastereoselective Bronsted acid catalyzed desymmetrization of 5-monosubstituted 1,3-dicarbonyl substrates with ortho-quinone methides gives rise to valuable tetrahydroxanthenes containing two distant stereocenters.

Bronsted acid catalyzed, conjugate addition of β-dicarbonyls to in situ generated ortho-quinone methides - Enantioselective synthesis of 4-aryl-4H-chromenes

We describe herein a catalytic, enantioselective process for the synthesis of 4H-chromenes which are important structural elements of many natural products and biologically active compounds. A sequence comprising a conjugate addition of β-diketones to in situ generated ortho-quinone methides followed by a cyclodehydration reaction furnished 4-aryl-4H-chromenes in generally excellent yields and high optical purity. A BINOL-based chiral phosphoric acid was employed as a Bronsted acid catalyst which converted ortho-hydroxy benzhydryl alcohols into hydrogen-bonded ortho-quinone methides and effected the carbon-carbon bond-forming event with high enantioselectivity. Chiral phosphoric acids permit the in situ generation of hydrogen-bonded ortho-quinone methides which react with β-diketones and β-keto esters with excellent enantioselectivity and furnish valuable 4-aryl-4H-chromenes and related heterocycles upon subsequent cyclodehydration. These observations extend the substrate scope of enantioselective phosphoric acid catalysis towards an important additional class of compounds.