3466-09-9

Usage

Uses

Used in Pharmaceutical Industry:
(2R)-2-Isopropenyl-8,9-dimethoxy-1,2-dihydro[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(12H)-one is used as a potential pharmaceutical candidate for various applications due to its complex structure and possible biological activities.
Used in Research and Development:
(2R)-2-Isopropenyl-8,9-dimethoxy-1,2-dihydro[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(12H)-one is used as a subject of research and development to explore its properties, potential uses, and to understand its full potential in various fields. Further experimentation and studies are necessary to harness its capabilities effectively.

InChI:InChI=1/C23H20O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16H,1,8,10H2,2-4H3/t16-/m1/s1

Upstream product

• 3276-13-9 Derritol 
• 105-36-2 ethyl bromoacetate 
• 93-59-4 Perbenzoic acid 
• 67-66-3 chloroform 
• 83-79-4 rotenone 
• 127-08-2 potassium acetate 
• 7664-41-7 ammonia 
• 64-17-5 ethanol 
• 7553-56-2 iodine 
• 67-64-1 acetone 
• 67-56-1 methanol 
• 34487-52-0 (2R,6aS,12aS)-8-hydroxy-9-methoxy-2-(prop-1-en-2-yl)-1,2,12,12a- tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one 

Downstream Products

• 3276-13-9 2-(2-hydroxy-4,5-dimethoxy-phenyl)-1-(4-hydroxy-2-isopropenyl-2,3-dihydro-benzofuran-5-yl)-ethanone 
• 6624-98-2 9-hydroxy-8-isopentyl-2,3-dimethoxy-6H-chromeno[3,4-b]chromen-12-one 
• 2847-34-9 {2-[2-(4-hydroxy-2-isopropenyl-2,3-dihydro-benzofuran-5-yl)-2-oxo-ethyl]-4,5-dimethoxy-phenoxy}-acetic acid 
• 41630-83-5 {2-[2-((R)-4-hydroxy-2-isopropenyl-2,3-dihydro-benzofuran-5-yl)-2-oxo-ethyl]-4,5-dimethoxy-phenoxy}-acetic acid ethyl ester 
• 4970-30-3 {2-[2-(4-hydroxy-2-isopropyl-benzofuran-5-yl)-2-oxo-ethyl]-4,5-dimethoxy-phenoxy}-acetic acid 
• 549-22-4 (+/-)-cis-isorotenone 
• 83-79-4 rotenone 
• 549-22-4 (+/-)-trans-isorotenone 
• 2847-34-9 {2-[2-((R)-4-hydroxy-2-isopropenyl-2,3-dihydro-benzofuran-5-yl)-2-oxo-ethyl]-4,5-dimethoxy-phenoxy}-acetic acid 

Relevant academic research and scientific papers

Continuous flow microchannel synthesis process of flavonoid compounds

The invention provides a continuous flow microchannel synthesis process of flavonoid compounds. According to the process, hesperidin and iodine elementary substance are used as raw materials and react in a continuous flow microchannel reactor in the presence of a reaction solvent to synthesize the flavonoid compound as shown in a formula A. Compared with a traditional kettle-type preparation process, the process disclosed by the invention has the advantages that the preparation time is obviously shortened, and the conversion rate of raw materials and the yield of products are obviously improved; and especially, when the diosmin is prepared under optimal process conditions of continuous flow microchannel synthesis, the conversion rate of the raw material hesperidin is as high as 96.48%, and the yield of the product diosmin is as high as 81.96%. The continuous flow micro-channel synthesis process provided by the invention is beneficial to realizing safe, efficient and rapid industrial production of flavonoid compounds, and has a wide application prospect.

Synthesis of trans-B/C-Rotenoids: X-Ray and NMR Data for cis- and trans-Forms of Isorotenone

Reduction of 6a,12a-didehydrorotenoids with diisobutylaluminium hydride gives clean 1,4-reduction leading to unstable trans-B/C-fusions, not previously known for enolisable rotenoids: they are epimerised to stable cis-forms under acid conditions.Applied initially to isorotenone, the method is extended to trans-B/C-deguelin, α-toxicarol, the 'core' rotenoid structure and the 6aS,12aR,5'R- and 6aR,12aS,5'R-rotenone stereoisomers. 1H and 13C NMR data are compared for the cis- and trans-forms and the geometry and conformations of the isorotenones are compared by X-ray analysis, providing insight into the reasons for the instability of the trans-forms.Reduction of the ridge-tile-like cis-isorotenone by sodium borohydride occurs from one face to give a cis-12α-hydroxy product, whilst the flatter trans-structure is attacked from both faces to give trans-12α- and 12β-hydroxy products.

STUDIES ON THE CHEMICAL TRANSFORMATION OF ROTENOIDS. II. REACTIONS OF ROTENONE AND ROTENONONE WITH PRIMARY AMINES

The ring transformations of rotenone and rotenonone by primary amines were investigated.The improved synthetic methods for rotenonone were also developed.Rotenone (1) underwent cleavage of C-12a and O-13 linkage to give alkylamines (2a-b), while rotenonone (5) gave 2-alkylcarbamoyl-4-alkylimino-8-methylethenyl-3-(2-hydroxy-4,5-dimethoxy)phenyl-8,9-dihydro-4H-furobenzopyrans (7a-d) as a result of nucleophilic attack on C-12 carbon.Compound 1 was oxidized bynitrosyl chloride or dimethyl sulfoxide in the presence of iodine and sulfuric acid to provide rotenonone (5) in improved yields respectively.

Regioselective Ether Cleavages of Rotenoids: Spiro-ether Formation and Stereoselective Isotopic Labelling of (E)- or (Z)-Phenyl Methyl Groups in (6aS, 12aS)-Rot-2'-enonic Acid

Treated with boron tribromide (-)-(6aS,12aS,5'R)-rotenone is converted first into a primary allylic bromide by ring-E cleavage, then into the 2-de-O-methyl and finally the 2,3-dide-O-methyl derivatives.With (6aS,12aS,5'R)-6',7'-dihydrorotenone and (6aS,12aS)-isorotenone, ring-E cleavage does not take place.The main reaction is 2-, followed by 2,3-demethylation: this supports a stereospecific pericyclic mechanism for the rotenone ring-E cleavage.Treatment of the geometrically pure (E)-bromide with cyanoboro-deuteride or -tritide leads to (E)-4'-labelled (6aS,12aS)-rot-2'-enonic acid without reduction of the 12-carbonyl group.By using -rotenone, (E)-rot-2'-enonic acid is accessible.Trimethylsilyl iodide can cleave the 2-methoxy-group of rotenonewithout rupturing ring E, and remethylation with - or -diazomethane represents a convenient method for preparing a general tracer molecule.On treatment with sodium hydride, 3-de-O-methylisorotenone (but not the 2-isomer) rearranges into a spiroether, thus confirming the position of initial de-O-methylation as deduced from 1H and 13C n.m.r. data.Because of this rearrangement, methylenation (NaH-CH2I2) of 2,3-dide-O-methylisorotenone gives mainly the methylenedioxy-spiro-ether, with small yields of methylenedioxy-rotenoid.Deuteriogenolysis of (-)-rotenone over palladium catalyst in (2H5)pyridine gives (E)-rot-2'-enonic acid, but experiments using rotenone indicate stereoselectivity rather than stereospecificity, ca. 12percent of (Z)--accompanying the major (E)-product.A similar specimen of rotenonic acid has been prepared.A hydrogenolysis route from amorphigenin, via rotenone, to (Z)-rot-2'-enonic acid is described.

Evaluation of rotenone and related compounds as antagonists of slow-reacting substance of anaphylaxis

Rotenone, dihydrorotenone, isorotenone, mutarotenone, and deguelin were found to be potent antagonists of slow-reacting substance of anaphylaxis (SRS-A) in vitro. However, these compounds were also shown to inhibit histamine, serotonin, and acetylcholine