50900-55-5

Upstream product

• 3698-23-5 Osmorhizole 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 1530-32-1 ethyltriphenylphosphonium bromide 
• 829-39-0 (E/Z)-2',4'-dimethoxy-1-propenylbenzene 
• 151-10-0 1,3-Dimethoxybenzene 
• 831-00-5 2,4-dimethoxypropiophenone 
• 830-99-9 1-(2,4-dimethoxyphenyl)propan-1-ol 

Downstream Products

• 36680-47-4 di-methyl ether of 4-n-propyl resorcinol 
• 831-00-5 2,4-dimethoxypropiophenone 
• 831-29-8 1-(2,4-dimethoxyphenyl)propan-2-one 
• 184900-71-8 (2R,3R)-6-Benzyloxy-2-(2,4-dimethoxy-phenyl)-3-methyl-2,3-dihydro-benzofuran-5-ol 

Relevant academic research and scientific papers

Synthesis, antiepileptic effects, and structure-activity relationships of α-asarone derivatives: In vitro and in vivo neuroprotective effect of selected derivatives

In the present study, we compared the antiepileptic effects of α-asarone derivatives to explore their structure-activity relationships using the PTZ-induced seizure model. Our research revealed that electron-donating methoxy groups in the 3,4,5-position on phenyl ring increased antiepileptic potency but the placement of other groups at different positions decreased activity. Besides, in allyl moiety, the optimal activity was reached with either an allyl or a 1-butenyl group in conjugation with the benzene ring. The compounds 5 and 19 exerted better neuroprotective effects against epilepsy in vitro (cell) and in vivo (mouse) models. This study provides valuable data for further exploration and application of these compounds as potential anti-seizure medicines.

Cobalt-Catalyzed Z to e Isomerization of Alkenes: An Approach to (E)-β-Substituted Styrenes

An efficient cobalt-catalyzed Z to E isomerization of β-substituted styrenes using the amido-diphosphine ligand was developed, delivering the (E)-isomers with good functional tolerance and high stereoselectivity. The reaction could be scaled up to gram-scale with a catalyst loading of 0.1 mol %, using a mixture of (Z)- and (E)-alkene as the starting material. Preliminary mechanistic studies indicated that cobalt(I)-hydride and a benzylic-cobalt species were probably involved in the reaction, as supported by experiments and DFT calculations.

Radical Cation Diels-Alder Reactions by TiO2 Photocatalysis

Radical cation Diels-Alder reactions by titanium dioxide (TiO2) photocatalysis in lithium perchlorate/nitromethane solution are described. TiO2 photocatalysis promotes reactions between electron-rich dienes and dienophiles, which would otherwise be difficult to accomplish due to electronic mismatching. The reactions are triggered by hole oxidation of the dienophile and are completed by the excited electron reduction of the radical cation intermediate at the dispersed surface in the absence of any sacrificial substrate.

Electronically Mismatched Cycloaddition Reactions via First-Row Transition Metal, Iron(III)-Polypyridyl Complex

The iron(III)-polypyridyl complex and its derivatives showed sufficient oxidizing potential to act as a one-electron oxidant, producing radical cations from olefins and promoting the efficient radical cation [2 + 2] and [2 + 4] cycloaddition reactions. Subsequent chain propagation afforded trisubstituted cyclobutane or cyclohexene derivatives, and this facile route enables the replacement of rare metals with sustainable, green, and inexpensive iron in radical cation cycloadditions.

Enantioselective Oxy-Heck–Matsuda Arylations: Expeditious Synthesis of Dihydrobenzofuran Systems and Total Synthesis of the Neolignan (?)-Conocarpan

This work discloses the first examples of an effective enantioselective oxy-Heck–Matsuda reaction using a variety of styrenic olefins to generate chiral dihydrobenzofurans. The reaction proceeds in moderate to good yields, with high trans diastereoselectivity (up to 20:1) in enantioselectivities up to 90:10 using the N,N-ligand pyrimidine-bisoxazoline (PyriBox). The oxy-Heck–Matsuda reactions were carried out under mild conditions and rather low catalyst loadings. The feasibility and practicality of the process is demonstrated by a concise total synthesis of the neolignan (?)-conocarpan. X-ray diffraction of an advanced brominated intermediate in the route to (?)-conocarpan has allowed the unequivocal assignment of the absolute stereochemistry of the oxy-Heck–Matsuda aryldihydrobenzofuran products. A rationale for the mechanism operating in these enantioselective oxy-Heck–Matsuda reactions is also presented. (Figure presented.).

Nonredox Metal-Ion-Accelerated Olefin Isomerization by Palladium(II) Catalysts: Density Functional Theory (DFT) Calculations Supporting the Experimental Data

Redox metal-ion-catalyzed olefin isomerization represents one of the important chemical processes. This work illustrates that nonredox metal ions can sharply accelerate Pd(II)-catalyzed olefin isomerization, while Pd(II) alone is very sluggish. Nuclear magnetic resonance (NMR) and ultraviolet-visible light (UV-vis) characterizations disclosed that the acceleration effect originates from the formation of heterobimetallic Pd(II) species with added nonredox metal ions, which improves the C-H activation capability of the Pd(II) moiety. Density functional theory (DFT) calculations further confirmed the sharp decrease of the energy barrier in C-H activation by the heterobimetallic Pd(II)/Al(III) species.

Photooxidizing chromium catalysts for promoting radical cation cycloadditions

The photooxidizing capabilities of selected CrIII complexes for promoting radical cation cycloadditions are described. These complexes have sufficiently long-lived excited states to oxidize electron-rich alkenes, thereby initiating [4+2] processes. These metal species augment the spectrum of catalysts explored in photoredox systems, as they feature unique properties that can result in differential reactivity from the more commonly employed ruthenium or iridium catalysts. Spotlight on chromium: Selected CrIII complexes were investigated for promoting radical cation cycloadditions. These species have sufficiently long-lived excited states to oxidize electron-rich alkenes, thereby initiating [4+2] processes. These metal complexes augment the spectrum of catalysts explored in photoredox systems, featuring properties that can result in differential reactivity from the more common Ru or Ir catalysts.

Stereoselective syntheses of substituted pterocarpans with anti-HIV activity, and 5-aza-/5-thia-pterocarpan and 2-aryl-2,3-dihydrobenzofuran analogues

Oxygenated pterocarpans and 5-azapterocarpans are prepared utilizing Lewis acid-promoted reactions of 2-alkoxy-1,4-benzoquinones with 2H-chromenes and N-tosyl-1,2-dihydroquinolines, respectively. Similarly, benzannulated analogues are prepared via reactions of 5-aIkoxy-1,4-naphthoquinones with chromenes, and related 2-aryl-2,3-dihydrobenzofurans result from reactions of styrenes with the quinones. Syntheses of 5-thiapterocarpans are also described utilizing Pd(0)-coupling of o-chloromercuriophenols with 2H-chromenes.