6054-00-8

Usage

InChI:InChI=1/C15H12O/c1-2-6-12(7-3-1)14-10-13-8-4-5-9-15(13)16-11-14/h1-10H,11H2

Upstream product

• 254-04-6 2H-chromene 
• 591-50-4 iodobenzene 
• 112635-45-7 C₁₅H₁₃BrO 
• 70340-04-4 (2-hydroxybenzyl)triphenylphosphonium bromide 
• 70-11-1 α-bromoacetophenone 
• 194665-78-6 2H-chromen-3-yl trifluoromethanesulfonate 
• 98-80-6 phenylboronic acid 
• 574-12-9 isoflavone 
• 90-01-7 salicylic alcohol 
• 80151-26-4 3-(2-chlorophenyl)-prop-2-yn-1-ol 
• 108-86-1 bromobenzene 
• 109790-41-2 [2-(2-oxo-2-phenylethoxy)benzyl]triphenylphosphonium bromide 
• 82381-21-3 (E)-β-[2-hydroxyphenylethylene]benzeneethanol 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 

Downstream Products

• 90878-07-2 2-(1-Ethyl-2-phenyl-allyl)-phenol 
• 4737-26-2 Isoflavan 
• 20879-06-5 (S)-3-phenylchromane 

Relevant academic research and scientific papers

Palladium-catalysed Intramolecular Arylation: a New Synthesis of Munduserone

Treatment of the aryl iodides (11) with palladium acetate gave the teracyclic stilbenes (13) via a formal but stereochemically disallowed Heck reaction; the method was exploited to synthesise (+/-)-munduserone (21).

Synthesis of multisubstituted cycloalkenes through carbomagnesiation of strained cycloalkynes

An efficient synthetic method of seven- and six-membered cycloalkenes through the generation of strained cycloalkynes and following carbomagnesiation is described. Further bond formations of the resulting cycloalkenylmagnesium intermediates with a wide variety of electrophiles enabled us to prepare diverse cycloalkene derivatives including benzoxepine analogs having a fully substituted alkene structure.

Benzopyrans compound as well as preparation method and application thereof

The invention relates to the field of the agricultural fungicide, and specifically relates to a benzopyrans compound as well as a preparation method and application thereof. The benzopyrans compound provided by the invention is simple in structure, easy to synthesize, low in production cost, and has a good inhibiting effect on the strawberry botrytis cinerea, potato altemaria solani, and watermelon fusarium oxysporum.

Iridium-Catalyzed Asymmetric Hydrogenation of 2H-Chromenes: A Highly Enantioselective Approach to Isoflavan Derivatives

A highly efficient (aS)-Ir/In-BiphPHOX-catalyzed asymmetric hydrogenation of substituted 2H-chromenes and substituted benzo[e][1,2]oxathiine 2,2-dioxides is described. A series of 2H-chromenes and benzo[e][1,2]oxathiine 2,2-dioxides were hydrogenated to give the target products in high yields (92-99%) with excellent enantioselectivities (up to 99.7% ee) using our catalytic system. This reaction provides a direct and efficient method for the construction of chiral benzo six-membered oxygen-containing compounds.

FeCl3-Catalyzed Ring-Closing Carbonyl–Olefin Metathesis

Exploiting catalytic carbonyl–olefin metathesis is an ongoing challenge in organic synthesis. Reported herein is an FeCl3-catalyzed ring-closing carbonyl–olefin metathesis. The protocol allows access to a range of carbo-/heterocyclic alkenes wi

Metal-ligand binding interactions in rhodium/palladium-catalyzed synthesis of dihydroquinolines

A domino Rh- and Pd-catalyzed synthesis of dihydroquinolines is disclosed. Two metals and two ligands are placed in one reaction vessel along with the two reactive reagents to afford selective sequential coupling despite the potential for side reactions.

2-Morpholinoisoflav-3-enes as flexible intermediates in the synthesis of phenoxodiol, isophenoxodiol, equol and analogues: Vasorelaxant properties, estrogen receptor binding and Rho/RhoA kinase pathway inhibition

Isoflavone consumption correlates with reduced rates of cardiovascular disease. Epidemiological studies and clinical data provide evidence that isoflavone metabolites, such as the isoflavan equol, contribute to these beneficial effects. In this study we developed a new route to isoflavans and isoflavenes via 2-morpholinoisoflavenes derived from a condensation reaction of phenylacetaldehydes, salicylaldehydes and morpholine. We report the synthesis of the isoflavans equol and deoxygenated analogues, and the isoflavenes 7,4′-dihydroxyisoflav-3-ene (phenoxodiol, haganin E) and 7,4′-dihydroxyisoflav-2-ene (isophenoxodiol). Vascular pharmacology studies reveal that all oxygenated isoflavans and isoflavenes can attenuate phenylephrine-induced vasoconstriction, which was unaffected by the estrogen receptor antagonist ICI 182,780. Furthermore, the compounds inhibited U46619 (a thromboxane A2 analogue) induced vasoconstriction in endothelium-denuded rat aortae, and reduced the formation of GTP RhoA, with the effects being greatest for equol and phenoxodiol. Ligand displacement studies of rat uterine cytosol estrogen receptor revealed the compounds to be generally weak binders. These data are consistent with the vasorelaxation activity of equol and phenoxodiol deriving at least in part by inhibition of the RhoA/Rho-kinase pathway, and along with the limited estrogen receptor affinity supports a role for equol and phenoxodiol as useful agents for maintaining cardiovascular function with limited estrogenic effects.

Synthesis of 2H-chromenes through the reduction of chromones with 9-BBN

Chromones were regioselectively reduced to 2H-1-benzopyrans through the 1,2-addition of 9-borabicyclo-[3.3.1]nonane. Although transition-metal complexes did not have a catalytic effect on the reaction, only by using palladium(II) chloride, could both 2H-1-benzopyran and dihydro-1-benzopyran be obtained to a similar extent. Also, the reduction of chromone using other organoboranes led not to 2H-1-benzopyran, but rather to chromanone through the reduction of only an olefin moiety.

A new route to 3,4-dihydro-2H-1-benzopyrans substituted at 3-position via palladium-catalysed reactions

3,4-Dihydro-2H-1-benzopyrans substituted at 3-position were prepared via palladium-catalysed reactions between a triflate and several coupling reagnets (alkyl or aryl tin reagents and borane derivatives) according to Stille or Suzuki methodologies.

Novel and Efficient Synthesis of Rotenoids via Intramolecular Radical Arylation

Treatment of the iodoarylchromenes 22 with palladium acetate gave the tetracyclic compounds 23 via a formal but stereochemically disallowed Heck reaction; a crystalline intermediate palladium species 25 (X-ray analysis) was isolated.The method was employe