1445876-92-5

Basic information

• Product Name: (R)-3'-O-methylviolanone
• CAS NO: 1445876-92-5
• Molecular Weight: 330.337
• Mol File: 1445876-92-5.mol

Chemical Properties

• CAS DataBase Reference: (R)-3'-O-methylviolanone(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3'-O-methylviolanone(1445876-92-5)
• EPA Substance Registry System: (R)-3'-O-methylviolanone(1445876-92-5)

Safety Data

• Hazardous Substances Data: 1445876-92-5(Hazardous Substances Data)

Upstream product

• 56973-42-3 3′-O-methylviolanone 
• 108-46-3 recorcinol 
• 76240-27-2 7-hydroxy-2,3-dihydro-4H-chromen-4-one 

Relevant articles and documents

A stereoselective switch: Enantiodivergent approach to the synthesis of isoflavanones

A modular six-step asymmetric synthesis of two naturally occurring and three non-natural isoflavanones containing tertiary α-aryl carbonyls is reported. This synthetic route, utilising a Pd-catalyzed decarboxylative asymmetric protonation, produces isoflavanones in excellent enantioselectivities from 76-97 %. A switch in the sense of stereoinduction was observed when different H+ sources were employed, showing the first example of dual stereocontrol in an asymmetric protonation reaction. The first enantioselective synthesis of the naturally occurring isoflavanones sativanone and 3-o-methylviolanone has been accomplished. Proton haze - Don′t know if I′m comin' up or down: The first asymmetric synthesis of the naturally occurring isoflavanones, sativanone and 3-O-methylviolanone, containing tertiary α-aryl carbonyls, has been accomplished. This was achieved through a Pd-catalyzed decarboxylative asymmetric protonation in excellent enantioselectivities from 76-97 %. A switch in the sense of stereoinduction was observed when different H+ sources were employed.

Dihydroisocoumarins and dihydroisoflavones from the rhizomes of dioscorea collettii with cytotoxic activity and structural revision of 2,2’-oxybis(1,4-di-tert-butylbenzene)

The investigation of the constituents of the rhizomes of Dioscorea collettii afforded one new dihydroisocoumarin, named (?)-montroumarin (1a), along with five known compounds—montroumarin (1b), 1,1’-oxybis(2,4-di-tert-butylbenzene) (2), (3R)-3′-O-methylviolanone (3a), (3S)-3′-O-methylviolanone (3b), and (RS)-sativanone (4). Their structures were elucidated using extensive spectroscopic methods. To the best of our knowledge, compound 1a is a new enantiomer of compound 1b. The NMR data of compound 2 had been reported but its structure was erroneous. The structure of compound 2 was revised on the basis of a reinterpretation of its NMR data (1D and 2D) and the assignment of the1H and13C NMR data was given rightly for the first time. Compounds 3a–4, three dihydroisoflavones, were reported from the Dioscoreaceae family for the first time. The cytotoxic activities of all the compounds were tested against the NCI-H460 cell line. Two dihydroisocoumarins, compounds 1a and 1b, displayed moderate cytotoxic activities, while the other compounds showed no cytotoxicity.