5452-46-0

Usage

InChI:InChI=1/C12H16O3/c1-4-5-10(13)9-6-7-11(14-2)12(8-9)15-3/h4,6-8,10,13H,1,5H2,2-3H3

Upstream product

• 2622-05-1 allylmagnesium bromide 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 1730-25-2 allylmagnesium bromide 
• 5597-50-2 3-(4-hydroxyphenyl)propionic acid methyl ester 
• 80696-81-7 4-bromo-5-(1-hydroxybut-3-en-1-yl)veratrole 
• 107-05-1 3-chloroprop-1-ene 
• 106-95-6 allyl bromide 
• 24850-33-7 allyltributylstanane 
• 591-87-7 Allyl acetate 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 

Downstream Products

• 115881-08-8 N-<1-(3,4-dimethoxyphenyl)but-3-en-1-yl>glutarimide 
• 880262-17-9 1-(3,4-dimethoxyphenyl)-2-oxiranylethanol 
• 1094999-08-2 C₁₅H₁₉BrO₃ 
• 115881-09-9 1-[1-(3,4-Dimethoxy-phenyl)-but-3-enyl]-6-hydroxy-piperidin-2-one 
• 115881-10-2 5-Oxo-pentanoic acid [1-(3,4-dimethoxy-phenyl)-but-3-enyl]-amide 
• 88931-04-8 (2RS,4RS,9aSR)-4-(3,4-dimethoxyphenyl)octahydro-2H-quinolizin-2-ol 
• 880262-22-6 2-[2-(3,4-dimethoxyphenyl)-2-(prop-2-ynyloxy)ethyl]oxirane 
• 57746-45-9 (+/-)-3c-(3.4-dimethoxy-phenyl)-cyclohexene-⁽⁴⁾-dicarboxylic acid-(1r.2c) 

Relevant academic research and scientific papers

Efficient solvent-free in situ tin-mediated homoallylation reactions

Various carbonyl compounds were converted to their corresponding homoallylic alcohols under ultrasonic irradiation and solvent free conditions, in the presence of metallic Sn and excess allyl bromide. Diallyltin(IV) dibromide was identified as the reactiv

Ni-Catalyzed 1,2-Diarylation of Alkenyl Ketones: A Comparative Study of Carbonyl-Directed Reaction Systems

A nickel-catalyzed 1,2-diarylation of alkenyl ketones with aryl iodides and arylboronic esters is reported. Ketones with a variety of substituents serve as effective directing groups, offering high levels of regiocontrol. A representative product is diversified into a wide range of useful products that are not readily accessible via existing 1,2-diarylation reactions. Preliminary mechanistic studies shed light on the binding mode of the substrate, and Hammett analysis reveals the effect of electronic factors on initial rates.

Photocatalytic Umpolung Synthesis of Nucleophilic π-Allylcobalt Complexes for Allylation of Aldehydes

The concept of "umpolung"reactivity of π-allylmetal complexes has been developed as a powerful method for the allylation of aldehydes. This paper describes the photocatalytic umpolung strategy for the synthesis of nucleophilic allylcobalt complexes through a single-electron-transfer (SET) process. This strategy enables the metallaphotoredox allylation of carbonyls with allyl acetate using organic N,N-diisopropylethylamine as the terminal reductant bypassing the use of a stoichiometric amount of metals. Ultraviolet-visible spectroscopy was used to monitor the redox changes of cobalt in the reaction.

MnO2as a terminal oxidant in Wacker oxidation of homoallyl alcohols and terminal olefins

Efficient and mild reaction conditions for Wacker-type oxidation of terminal olefins of less explored homoallyl alcohols to β-hydroxy-methyl ketones have been developed by using a Pd(ii) catalyst and MnO2 as a co-oxidant. The method involves mild reaction conditions and shows good functional group compatibility along with high regio- and chemoselectivity. While our earlier system of PdCl2/CrO3/HCl produced α,β-unsaturated ketones from homoallyl alcohols, the present method provided orthogonally the β-hydroxy-methyl ketones. No overoxidation or elimination of benzylic and/or β-hydroxy groups was observed. The method could be extended to the oxidation of simple terminal olefins as well, to methyl ketones, displaying its versatility. An application to the regioselective synthesis of gingerol is demonstrated.

Enantioselective Synthesis of Isoxazolines Enabled by Palladium-Catalyzed Carboetherification of Alkenyl Oximes

Reported here is a highly efficient Pd/Xiang-Phos catalyzed enantioselective carboetherification of alkenyl oximes with either aryl or alkenyl halides, delivering various chiral 3,5-disubstituted and 3,5,5-trisubstituted isoxazolines in good yields with u

Active bismuth mediated allylation of carbonyls/N-tosyl aldimines and propargylation of aldehydes in water

Abstract: Active bismuth is synthesized by the chemical reduction of bismuth trichloride using freshly prepared sodium stannite solution as the reducing agent at room temperature. The as-synthesized active bismuth is applied as a reagent for the synthesis of homoallyl alcohol/homopropargyl alcohol from allyl bromide/propargyl bromide and carbonyl compounds in water at 50°C. The homoallyl amines are also synthesized from N-tosyl aldimines and allyl bromide using active bismuth reagent in good yields. No assistance of organic co-solvent, co-reagent, phase transfer catalyst or inert atmosphere is required for this reaction. The waste bismuth material obtained after the completion of the organic reaction can be reduced to active bismuth by sodium stannite solution and successfully reused for mediating the allylation of aldehydes. Graphical Abstract:: Synopsis Active bismuth mediated allylation/crotylation of aldehydes is developed in water to get homoallyl alcohols. The method is also applied for the allylation of N-tosyl aldimines and propargylation of aldehydes in water to achieve the homoallyl amines and homopropargyl alcohols, respectively. The reactions do not require the assistance of organic co-solvent, co-reagent, phase transfer catalyst or inert atmosphere.[Figure not available: see fulltext.].

Palladium-Mediated Remote Functionalization in γ- And ?-Arylations and Alkenylations of Unblocked Cyclic Enones

We report herein an extensive investigation of simple and regioselective endo- as well as exo-γ-arylations of silyl-dienol ethers of unblocked cyclic enones with the utilization of palladium-catalyzed, modified Kuwajima-Urabe conditions. We have also successfully explored a new exo-?-arylation of silyl-trienol ethers of π-extended cyclic enones. In addition, we also report, herein, exclusive γ- and ?-alkenylation of silyl-dienol and silyl-trienol ethers of cyclic enones.

Water-Compatible Synthesis of 2-Trifluoromethyl-1,3-Dioxanes

A water-compatible method for the diastereoselective synthesis of 2-trifluormethyl-1,3-dioxanes is described. The reaction proceeds under mild reaction conditions using simple inorganic bases; it has a very good substrate scope and can be performed with different Michael acceptors. Additionally, the reaction products can be further functionalized, showing an excellent perspective for future applications.

CuI catalyzed Barbier type allylation of aldehyde in presence of S1,S2-dipyridin-2-yl ferrocene-1,1′-dicarbothioate as ligand

Ferrocene based ligand S1 ,S2-dipyridin-2-yl ferrocene-1,1′-dicarbothioate has been prepared from 1,1′-ferrocene-dicarboxylic acid. The ligand has been used successfully in the SnCl2.2H2O mediated Barbier type a

Synthesis and anti-inflammatory activity of phenylbutenoid dimer analogs

Several phenylbutenoid dimer (PBD) analogs were synthesized and evaluated for their inhibitory activities against nitric oxide (NO) production and TNF-α release. The PBD analogs were synthesized via Diels - Alder and subsequent Schlosser reactions as key steps. Among the tested compounds, two analogs (8c, 8f) exhibited much stronger inhibitory activity against LPS-stimulated NO production and TNF-α release in RAW 264.7 cells than that of wogonin.