40359-62-4

Usage

InChI:InChI=1/C10H9BrO2/c1-2-5-13-10-4-3-9(11)6-8(10)7-12/h2-4,6-7H,1,5H2

Upstream product

• 181280-10-4 2-allyloxy-5-bromo-benzaldehyde oxime 
• 106-95-6 allyl bromide 
• 1761-61-1 5-bromosalicyclaldehyde 

Downstream Products

• 18385-87-0 6-bromo-2H-benzopyran 
• 1314234-86-0 tert-butyl N-[5-bromo-2-(prop-2-en-1-yloxy)phenyl]methylidenecarbamate 
• 1314234-88-2 tert-butyl N-{[5-bromo-2-(prop-2-en-1-yloxy)phenyl](3,3-dimethylcycloprop-1-en-1-yl)methyl}carbamate 
• 1314234-71-3 [5-bromo-2-(prop-2-en-1-yloxy)phenyl](3,3-dimethylcycloprop-1-en-1-yl)methanol 
• 1536075-29-2 1-(2-(allyloxy)-5-bromophenyl)-2,2,2-trichloroethanol 
• 62176-23-2 2-(allyloxy)-5-bromobenzoic acid 

Relevant academic research and scientific papers

tert-Butyl Hydroperoxide-Initiated Radical Cyclization of 1-(Allyloxy)-2-(1-Arylvinyl)Benzenes with Sulfinic Acids to Access Sulfonated Benzoxepines

A tert-butyl hydroperoxide-initiated radical cyclization of 1-(allyloxy)-2-(1-arylvinyl)benzenes with sulfinic acids for the construction of sulfonated benzoxepines is developed. This reaction involves a radical pathway and offers a straightforward route to the formation of seven-membered ring via sulfonylation/cyclization process. This methodology features mild reaction conditions, a broad substrate scope and good functional group tolerance. (Figure presented.).

Visible-Light-Promoted Cascade Radical Cyclization: Synthesis of 1,4-Diketones Containing Chroman-4-One Skeletons

A visible-light-induced cascade radical cyclization of aroyl chlorides with 2-(allyloxy)-benzaldehyde derivatives has been developed. The method takes advantages of unactivated C=C bonds as the acyl radical acceptors and offers a mild and green approach for the synthesis of 1,4-diketones bearing biologically important chroman-4-one skeletons with moderate to good yields.

Synthesis of chroman-4-one and indanone derivatives via silver catalyzed radical ring opening/coupling/cyclization cascade

A variety of chroman-4-one and indanone derivatives were conveniently synthesized from readily available cyclopropanols and alkenyl aldehydes via a silver catalyzed radical ring-opening/coupling/cyclization cascade. The reaction proceeded under mild and neutral conditions with broad substrate scope and afforded the desired products in moderate to good yields. A probable mechanism for the cascade reaction was also proposed.

BENZOCYCLOBUTANE DERIVATIVES USEFUL AS DUAL SGLT1/SGLT2 MODULATORS

The present invention is directed to benzocyclobutane derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by SGLT activity, more particularly dual SGLT1/2 activity. More particularly, the compounds of the present invention are useful in the treatment of for example, Type II diabetes mellitus, Syndrome X, and complications and symptoms associated with said disorders.

Tetrahydrobenzochromene Synthesis Enabled by a Deconjugative Alkylation/Tsuji-Saegusa-Ito Oxidation on Knoevenagel Adducts

A modular and practical route to versatile cyano-1,3-dienes by a sequence involving deconjugative alkylation and "Tsuji-Saegusa-Ito oxidation" is reported. In this letter, the versatility of the products is also explored, including a route to benzochromene scaffolds common to many natural products.

Silver-Catalyzed Radical Cascade Cyclization toward 1,5-/1,3-Dicarbonyl Heterocycles: An Atom-/Step-Economical Strategy Leading to Chromenopyridines and Isoxazole-/Pyrazole-Containing Chroman-4-Ones

A novel and convenient silver-catalyzed radical cascade cyclization toward a large variety of 1,5-/1,3-dicarbonyl heterocycles containing a chroman-4-one, indanone, or 2,3-dihydroquinolin-4(1H)-one moiety was developed, by reacting various 2-functionalized benzaldehydes, including 2-allyloxy benzaldehydes, 2-allyl benzaldehyde, and 2-N(Ts)CH2-CH CH2 substituted benzaldehyde, with 1,3-dicarbonyl compounds in the presence of AgNO3/K2S2O8 in one pot under mild reaction conditions. The newly obtained 1,5-/1,3-dicarbonyl-containing heterocycles were further used directly to synthesize more structurally diverse polyheterocycles, mainly including chromenopyridines as well as isoxazole- or pyrazole-containing chroman-4-ones.

Catalytic Intramolecular Cycloaddition Reactions by Using a Discrete Molecular Architecture

A discrete tetragonal tube-shaped complex (MT-1) has been synthesised by coordination-driven self-assembly of a carbazole-based tetraimidazole donor L and a Pd(II) 90° acceptor, that is, [cis-(dppf)Pd(OTf)2] (dppf=diphenylphosphinoferrocene, OTf=CF3SO3?). Complex MT-1 was characterised by multinuclear NMR, ESI-MS and single-crystal X-ray diffraction analysis (SCXRD), which showed its symmetrical tetrafacial tube-shaped architecture possessing a large cavity described by four aromatic walls. This coordination cage was successfully utilised as a molecular vessel to perform intramolecular cycloaddition reactions of O-allylated benzylidinebarbituric acid derivatives inside its confined nanospace. The presence of a catalytic amount of MT-1 promoted [4+2] cycloaddition reactions in a regio- and stereoselective manner, yielding the corresponding penta/tetracyclouracil derivatives in good yields under mild reaction conditions. This protocol is interesting compared with the literature reports for the synthesis of similar chromenopyran pyrimidinedione derivatives under high-temperature reflux conditions or solid-state melt reactions (SSMRs).

Straightforward synthesis of functionalized chroman-4-ones through cascade radical cyclization-coupling of 2-(allyloxy)arylaldehydes

A novel and direct approach to synthesize a series of phosphonate, azide and hydroxy functionalized chroman-4-ones has been developed. The cascade transformation appears to proceed through an intramolecular addition of an in situ generated acyl radical onto the alkene, followed by a selective nucleophilic radical-electrophilic radical cross coupling.

Organoselenium and DMAP co-catalysis: Regioselective synthesis of medium-sized halolactones and bromooxepanes from unactivated alkenes

A catalytic system consisting of bis(4-methoxyphenyl)selenide and 4-(dimethylamino)pyridine (DMAP) has been developed for the regioselective synthesis of medium-sized bromo/iodo lactones and bromooxepanes possessing high transannular strain. 77Se NMR, mass spectrometry and theoretical studies reveal that the reaction proceeds via a quaternary selenium intermediate.

One-pot synthesis of 5-amino-2,5-dihydro-1-benzoxepines: Access to pharmacologically active heterocyclic scaffolds

A one-pot multibond-forming process involving a thermally mediated Overman rearrangement and a ring closing metathesis reaction of allylic trichloroacetimidates bearing a 2-allyloxyaryl group has been developed for the synthesis of 5-amino-substituted 2,5-dihydro-1-benzoxepines. Chemoselective reduction and functionalization of these compounds allowed access to a range of pharmacologically active 5-amino-2,3,4,5-tetrahydro-1-benzoxepine scaffolds.