18075-40-6

Usage

Uses

Used in Pharmaceutical Industry:
3-Allyloxy-4-methoxybenzaldehyde is used as an intermediate in the synthesis of Diosmetin 3',7-Diglucuronide (D485040), a metabolite of Diosmetin (D485000). Diosmetin is a flavonoid commonly used in the treatment of chronic venous insufficiency, hemorrhoids, and related conditions. The synthesis of this metabolite allows for the development of more effective treatments and pharmaceutical formulations for these medical conditions.

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

Upstream product

• 52507-49-0 4-hydroxy-3-(2-propenyloxy)benzaldehyde 
• 74-88-4 methyl iodide 
• 621-59-0 isovanillin 
• 106-95-6 allyl bromide 

Downstream Products

• 99661-59-3 (E)-3-(3-Allyloxy-4-methoxy-phenyl)-thioacrylamide 
• 179128-85-9 (E)-3-[3-(allyloxy)-4-methoxyphenyl]acrylic Acid 
• 188255-39-2 3-isopropoxy-4-methoxy-2-(prop-2'-enyl)benzaldehyde 
• 854954-43-1 O-allylisovanillyl alcohol 
• 847144-91-6 3-acetyl-4-[3-(allyloxy)-4-methoxyphenyl]but-3-enoic acid 
• 57189-64-7 1,2-dimethoxynaphthalene 
• 374073-56-0 1-(2-allyl-3,4-dimethoxyphenyl)prop-2-en-1-ol 
• 374073-59-3 1-(2-allyl-3-ethoxy-4-methoxyphenyl)prop-2-en-1-ol 
• 374073-60-6 1-[2-allyl-3-(benzyloxy)-4-methoxyphenyl]prop-2-en-1-ol 
• 778638-70-3 7-ethoxy-6-methoxyindene 
• 812646-82-5 5-ethoxy-6-methoxy-1-naphthol 
• 778638-68-9 2-allyl-3,4-dimethoxy-1-vinylbenzene 
• 778638-77-0 2-allyl-3-ethoxy-4-methoxy-1-vinylbenzene 
• 812646-72-3 1-(2-allyl-3,4-dimethoxy-phenyl)-propenone 

Relevant academic research and scientific papers

Iodine-DMSO catalyzed chemoselective oxidative aromatization and deallylation, nondeallylation of aryl allyl ether of tetrahydro-β-carboline

We have developed a simple method for the chemoselective aromatization of tetrahydro-β-carboline with selective nondeallylation O-allyl groups in the presence of iodine (100 mol %) in dimethyl sulfoxide/H2O2. A convergent approach toward the oxidative aromatization with selective deallylation (deprotection) of O-allyl-tetrahydro-β-carboline using iodine in dimethyl sulfoxide/HCl has been described. The present protocol contains cheap catalyst, easy work up, normal reaction conditions, and high selectivity.

Enantiopure C1-Cyclotriveratrylene with a Reversed Spatial Arrangement of the Substituents

Cyclotriveratrylene (CTV) is a macrocyclic cyclophane presenting a bowl-shaped conformation, used as building block to construct cryptophane and hemicryptophane capsules. A method to synthesize new enantiopure CTV derivatives with an unprecedented spatial

TBuO 2H/Cu(acac) 2-Mediated Intramolecular Oxidative Lactonization of o -Allyl Arylaldehydes: Synthesis of 1-Oxoisochromans

A concise route for the tBuO 2H/Cu(acac) 2-mediated synthesis of 1-oxoisochromans is described. This includes: (i) oxidation of oxygenated o -allyl arylaldehydes and (ii) sequential intramolecular lactonization of the resulting olefin-containing benzoic acids. A plausible mechanism is proposed and discussed.

PdCl2/CuCl2/Bi(OTf)3-promoted Construction of Sulfonyl Dibenzooxabicyclo[3.3.1]nonanes and Arylnaphthalenes via Intramolecular Annulation of Sulfonyl o-Allylarylchromanones

PdCl2/CuCl2/Bi(OTf)3-promoted intramolecular domino annulation of sulfonyl o-allylarylchromanones provides tetracyclic sulfonyl dibenzooxabicyclo[3.3.1]nonanes and bicyclic arylnaphthalenes with good to excellent yields in MeOH at room (25 °C) and refluxing (65 °C) temperature, respectively. The starting sulfonyl o-allylarylchromanones can be easily obtained from the intermolecular cyclocondensation of α-sulfonyl o-hydroxyacetophenones and o-allylbenzaldehydes. The uses of various catalysts and solvent systems are investigated herein for convenient transformation. A plausible mechanism is proposed and discussed. This protocol provides one-pot ring closure via carbon-carbon (C?C) bond formation. (Figure presented.).

Concise Synthesis of the ABC-Ring System of the Azafluoranthene, Tropoisoquinoline and Proaporphine Alkaloids: An Olefin Hydroacylation/Pomeranz-Fritsch Cyclization Approach

A straightforward approach toward a decorated cyclopenta[ ij ]isoquinoline embodying the ABC-ring system characteristic of the azafluoranthene (triclisine), tropoisoquinoline (pareitropone) and proaporphine (prodensiflorin B) alkaloids, is reported. The s

Diethylaminosulfur Trifluoride (DAST)-Mediated Intramolecular Benzannulation of o-Allylchalcones: Synthesis of 3-Fluorotetralins

A concise route for the synthesis of 3-fluorotetralines is described, including: (i) NaBH 4 -mediated reduction of oxygenated o -allylchalcones and (ii) sequential DAST-mediated intramolecular annulation of the resulting alkenols. A plausible m

Biomimetic Syntheses of (±)-Isopalhinine A, (±)-Palhinine A, and (±)-Palhinine D

The first total synthesis of isopalhinine A, as well as unified syntheses of palhinine A and palhinine D, were successfully accomplished by means of a biomimetic strategy that proceeds through a bioinspired 5/6/6/9 tetracyclic intermediate, which mimics t

Synthesis of Polysubstituted 3-Methylisoquinolines through the 6π-Electron Cyclization/Elimination of 1-Azatrienes derived from 1,1-Dimethylhydrazine

A convenient one pot microwave-assisted 6π-electron cyclization/aromatization approach toward 3-methylisoquinolines is reported. The starting 1-azatriene derivatives were prepared in situ by reaction of 2-propenylbenzaldehydes with 1,1-dimethylhydrazine, which exhibited superior performance when compared with other hydrazine derivatives. Minor amounts of the related 3,4-dihydro isoquinolines were formed concomitantly with the isoquinolines, and a mechanism for their generation was proposed. The reaction conditions were optimized, and its scope and limitations were explored. In general, the transformation proceeded in moderate to good yields.

Sodium Perborate: A Facile Catalyst for Allylation of Active Centers

An efficient and ecofriendly allylation of O-H, N-H, and C-H groups has been achieved successfully with the reaction of allyl bromide by using sodium perborate as a new catalyst in aqueous media. The advantage of this method is operationally simple, short reaction time, good yield, and simple workup conditions over the previously reported conventional methods such as amination, oxyalkylation reactions of allyl bromide, and Friedel-Crafts allylation chemistry.

A Biomimetic Strategy to Access the Silybins: Total Synthesis of (-)-Isosilybin A

(Figure Presented). We report the first asymmetric, total synthesis of (-)-isosilybin A. A late-stage catalytic biomimetic cyclization of a highly functionalized chalcone is employed to form the characteristic benzopyranone ring. A robust and flexible app