31456-98-1

Usage

InChI:InChI=1/C11H12O3/c1-3-5-8-6-4-7-9(10(8)12)11(13)14-2/h3-4,6-7,12H,1,5H2,2H3

Upstream product

• 140706-70-3 methyl 3-oxo-4-(2-propenyl)hept-6-enoate 
• 7631-93-8 sodium o-methoxycarbonylphenolate 
• 140706-84-9 methyl 3-(2-propenyl)-2-hydroxycyclohexa-1,4-diene-1-carboxylate 
• 69-72-7 salicylic acid 
• 119-36-8 methyl salicylate 
• 106-95-6 allyl bromide 
• 140706-74-7 methyl 2-chloro-3-oxo-4-(2-propenyl)hept-6-enoate 
• 6282-42-4 methyl 2-allyloxybenzoate 

Downstream Products

• 91715-56-9 3-Formylmethyl-salicylsaeure-methylester 
• 866528-96-3 3-((E)-Propenyl)-2-trifluoromethanesulfonyloxy-benzoic acid methyl ester 
• 99517-45-0 methyl benzofuran-7-carboxylate 
• 53433-99-1 3-allyl-salicylohydrazide 
• 861564-62-7 3-(2,3-dibromo-propyl)-2-hydroxy-benzoic acid 
• 31457-07-5 2-methyl-7-benzofurancarbonsaeure 
• 861604-30-0 3,5-diallyl-2-allyloxy-benzoic acid 
• 861531-12-6 3,5-diallyl-2-allyloxy-benzoic acid methyl ester 
• 92252-07-8 3,5-diallyl-2-hydroxy-benzoic acid methyl ester 
• 861530-40-7 3-allyl-2-allyloxy-benzoic acid 
• 860756-99-6 3,5-diallyl-2-hydroxy-benzoic acid 
• 3383-04-8 1,3-di(prop-2-en-1-yl)-2-[(prop-2-en-1-yl)-oxy]benzene 
• 20490-22-6 2,4,6-tris(2-propenyl)phenol 
• 74663-50-6 2,4,6-tri-n-Propylphenol 

Relevant academic research and scientific papers

Subsupercritical Water Generated by Inductive Heating Inside Flow Reactors Facilitates the Claisen Rearrangement

Claisen rearrangement of electron-deficient O-allylated phenols, including fluorine-modified phenols, is facilitated in aqueous media at high temperatures and pressures under flow conditions, as opposed to organic solvents. The O-allylation of phenols can be coupled with the Claisen rearrangement in an integrated flow system.

Discovery of orthogonal synthesis using artificial intelligence: Pd(OAc)2-catalyzed one-pot synthesis of benzofuran and bicyclo[3.3.1]nonane scaffolds

A synthetic route for the common intermediate, methyl 2-formylbenzofuran-7-carboxylate (7a), to efficiently assemble three bioactive benzofurans 4–6 was explored using the artificial intelligence system SYNSUP. Among the routes proposed by SYNSUP, we investigated a three-step synthesis of 7a using methyl 4-ally-3-oxohept-6-enoate (10). A new catalytic reaction was found in which 7a was directly obtained from 10 in a single step with a yield of 24percent. It was found that this chemical yield could be increased to 74percent when methyl 3-allyl-2-hydroxybenzoate (9a), an intermediate of the above one-pot transformation, was subjected to the catalytic process. In addition, in this catalytic process, 8a (76percent) and 11 (77percent) were each selectively synthesized from 10 by changing only the solvent. Therefore, we created a novel orthogonal synthesis of methyl 2-methylbenzofuran-7-carboxylate (8a) and methyl 9-oxobicyclo[3.3.1]nona-3,6-diene-1-carboxylate (11). Finally, the total syntheses of bioactive benzofurans 4–6 were completed smoothly using 7a and 8a.

Small-molecules that covalently react with a human prolyl hydroxylase-towards activity modulation and substrate capture

We describe covalently binding modulators of the activity of human prolyl hydroxylase domain 2 (PHD2) and studies towards a strategy for photocapture of PHD2 substrates. Reversible active site binding of electrophile bearing compounds enables susbsequent covalent reaction with a lysine residue (K408) in the flexible C-terminal region of PHD2 to give a modified protein that retains catalytic activity.

Fluorescence sensing of dichlorvos pesticide by the luminescent Tb(III)-3-ally-salicylohydrazide probe

A fluorescent probe was developed and characterized, it consisted of terbium(III) with 3-ally-salicylohydrazide in ethanol, in which the 1:2 [Tb3+:S1] molar ratio was the best stoichiometric ratio for the probe. The ligand 3-ally-sal

Discovery and structure-activity relationship of novel 2,3- dihydrobenzofuran-7-carboxamide and 2,3-dihydrobenzofuran-3(2 h)-one-7-carboxamide derivatives as poly(ADP-ribose)polymerase-1 Inhibitors

Novel substituted 2,3-dihydrobenzofuran-7-carboxamide (DHBF-7-carboxamide) and 2,3-dihydrobenzofuran-3(2H)-one-7-carboxamide (DHBF-3-one-7-carboxamide) derivatives were synthesized and evaluated as inhibitors of poly(ADP-ribose) polymerase-1 (PARP-1). A structure-based design strategy resulted in lead compound 3 (DHBF-7-carboxamide; IC50 = 9.45 μM). To facilitate synthetically feasible derivatives, an alternative core was designed, DHBF-3-one-7-carboxamide (36, IC50 = 16.2 μM). The electrophilic 2-position of this scaffold was accessible for extended modifications. Substituted benzylidene derivatives at the 2-position were found to be the most potent, with 3′,4′-dihydroxybenzylidene 58 (IC50 = 0.531 μM) showing a 30-fold improvement in potency. Various heterocycles attached at the 4′-hydroxyl/4′-amino of the benzylidene moiety resulted in significant improvement in inhibition of PARP-1 activity (e.g., compounds 66-68, 70, 72, and 73; IC50 values from 0.718 to 0.079 μM). Compound 66 showed selective cytotoxicity in BRCA2-deficient DT40 cells. Crystal structures of three inhibitors (compounds (-)-13c, 59, and 65) bound to a multidomain PARP-1 structure were obtained, providing insights into further development of these inhibitors.

Studies towards the total synthesis of Sch 56036; isoquinolinone synthesis and the synthesis of phenanthrenes

The isoquinolinone hemisphere of Sch 56036 has been prepared using a modified Pomeranz-Fritsch reaction and the synthesis of the phenanthrene core has been modelled via a Suzuki coupling and subsequent ring closing metathesis.

A domino amidation route to indolines and indoles: Rapid syntheses of anhydrolycorinone, hippadine, oxoassoanine, and pratosine

(Chemical Equation Presented) When subjected to palladium-catalyzed amidation conditions, 2-triflyloxy phenethyl carbonates undergo, in addition to the expected aryl cross-coupling, an additional amidation with net displacement of the carbonate. The result is a one-step synthesis of indolines which may be oxidized to indoles. The utility of the procedure is illustrated by the two- or three-step syntheses of anhydrolycorinone, hippadine, oxoassoanine, and pratosine.

BENZODIOXOLE, BENZOFURAN, DIHYDROBENZOFURAN, AND BENZODIOXANE MELATONERGIC AGENTS

Novel derivatives of benzodioxa alkylene ethers are provided which are useful as melatonergic agents.

Synthesis and vasorelaxant potency of monagra. A chiral 5-(2-methyl-2,3-dihydro-7-benzofuryl)-pyrazolopyrimidone analog of viagra

Synthesis and properties of a chiral 5-(2-methyl-2,3-dihydro-7-benzofuryl)pyrazolo[4,3-d]pyrimidin-7-one (3), an analog of Viagra (1) and Biagra (2), are described. The key material, (±)-3-methyl-2,3-dihydrobenzofuran-7-carboxylic acid (8a) was resolved into the (S)-8b (95% ee) and (R)-8c (99% ee) enantiomers using, respectively, (-)-cinchonidine and (+)-cinchonine. The absolute configuration of 8c was determined as R by X-Ray measurements. Preliminary in vitro experiments on rat isolated thoracic aorta show that the vasorelaxant potency of 3b,c is truly higher than that of 1 and 2.

Heterocyclic compounds: 2-styryl-4H-1-benzopyran-4-ones

A compound of the formula (I) STR1 in which: R1 represents a hydrogen atom, a lower alkyl group, a hydroxy group or a lower alkoxy group, R2, R3, R4, R5, R6, R7, R8 an