35106-82-2

Usage

General Description

(2-Vinylphenyl)methanol, also known as styrenyl methanol, is a chemical compound that belongs to the class of phenylmethyl alcohols. It is a colorless to pale yellow liquid with a characteristic odor. It is mainly used as an intermediate for the synthesis of various chemicals, including pharmaceuticals, agrochemicals, and flavor and fragrance compounds. It also finds applications in the production of polymers and resins. However, it is important to handle (2-Vinylphenyl)methanol with care as it can cause skin and eye irritation upon contact, and it is flammable in nature. Overall, (2-Vinylphenyl)methanol is a versatile chemical with diverse industrial applications.

Upstream product

• 28272-96-0 2-vinylbenzaldehyde 
• 27326-44-9 methyl o-vinylbenzoate 
• 57056-91-4 1-[(ethenoxy)methyl]-2-iodobenzene 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 5159-41-1 2-iodobenzyl alcohol 
• 1826-67-1 vinyl magnesium bromide 
• 18982-54-2 o-bromobenzyl alcohol 
• 4122-56-9 methyl o-formylbenzoate 
• 27326-43-8 2-vinylbenzoic acid 
• 74-85-1 ethene 
• 10602-08-1 2-ethynylbenzyl alcohol 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 612-14-6 phthalyl alcohol 
• 6630-33-7 ortho-bromobenzaldehyde 

Downstream Products

• 28272-96-0 2-vinylbenzaldehyde 
• 22570-84-9 2-chloromethylstyrene 
• 656807-25-9 2-(2-vinylphenyl)acetonitrile 
• 763082-26-4 2-ethenyl-N-2-propenyl-benzeneethaneamine 
• 762239-29-2 2-ethenyl-N-3-butenyl-benzeneethaneamine 
• 1319203-99-0 C₂₃H₃₂O₂Si 
• 1319203-97-8 C₁₇H₁₈O₂ 
• 73357-78-5 vinylbenzyl bromide 
• 1396690-23-5 2-vinylbenzyl formate 
• 1569076-57-8 C₃₁H₃₀N₂O₃S₂ 

Relevant academic research and scientific papers

Diastereoselective Synthesis of the ABCD Ring System of Rubriflordilactone B

A novel nine-step diastereoselective route to the ABCD ring system of the natural product rubriflordilactone B is reported. Use of an α-substituted butenolide derived from maleic anhydride facilitated a 1,4-conjugate addition to provide a diene. The order in which a ringclosing metathesis and enolate oxidation were performed on this compound dictated the relative stereochemistry of the target. The final product exhibited anisotropic effects during roomerature NMR studies, requiring elevatederature experiments to confirm its identity.

Copper-Catalyzed Modular Amino Oxygenation of Alkenes: Access to Diverse 1,2-Amino Oxygen-Containing Skeletons

Copper-catalyzed alkene amino oxygenation reactions using O-acylhydroxylamines have been achieved for a rapid and modular access to diverse 1,2-amino oxygen-containing molecules. This transformation is applicable to the use of alcohols, carbonyls, oximes, and thio-carboxylic acids as nucleophiles on both terminal and internal alkenes. Mild reaction conditions tolerate a wide range of functional groups, including ether, ester, amide, carbamate, and halide. The reaction protocol allows for starting with free amines as the precursor of O-benzoylhydroxylamines to eliminate their isolation and purification, contributing to broader synthetic utilities. Mechanistic investigations reveal the amino oxygenation reactions may involve distinct pathways, depending on different oxygen nucleophiles.

Enantioselective Copper-Catalyzed Desymmetrization of 1,3-Diketones Involving Borylation of Styrenes

A copper-catalyzed intramolecular enantioselective and diastereoselective borylative coupling of styrenes and ketones was achieved by merging desymmetrization strategy and olefin difunctionalization. The reaction proceeds through an initial enantioselective borylcupration of styrenes, followed by a highly selective direct addition to 1,3-diketones. The bicyclic scaffolds with three chiral carbon centers, including two tetrasubstituted carbons, were generated in excellent yields, diastereoselectivities, and enantioselectivities. This catalytic tandem reaction has great potential for further synthetic application of the chiral polycyclic compounds, because of the versatility of the functional groups in the products.

Synthesis of Phthalans Via Copper-Catalyzed Enantioselective Cyclization/Carboetherification of 2-Vinylbenzyl Alcohols

Enantiomerically enriched phthalans were synthesized efficiently via an enantioselective copper-catalyzed alkene carboetherification reaction. In this reaction, 2-vinylbenzyl alcohols enantioselectively cyclize then couple with vinylarenes. The utility of the method was demonstrated by the enantioselective synthesis of (R)-fluspidine, a σ1 receptor ligand.

Direct Wittig Olefination of Alcohols

A base-promoted transition metal-free approach to substituted alkenes using alcohols under aerobic conditions using air as the inexpensive and clean oxidant is described. Aldehydes are relatively difficult to handle compared to corresponding alcohols due to their volatility and penchant to polymerize and autoxidize. Wittig ylides are easily oxidized to aldehydes and consequently form homo-olefination products. By the strategy of simultaneously in situ generation of ylides and aldehydes, for the first time, alcohols are directly transferred to olefins with no need of prepreparation of either aldehydes or ylides. Thus, the di/monocontrollable olefination of diols is accomplished. This synthetically practical method has been applied in the gram-scale synthesis of pharmaceuticals, such as DMU-212 and resveratrol from alcohols.

Stable Zero-Valent Nickel Nanoparticles in Glycerol: Synthesis and Applications in Selective Hydrogenations

Small (mean diameter, ca. 1.2 nm) and well-dispersed zero-valent nickel nanoparticles (NiNPs) stabilized by cinchona-based alkaloids and TPPTS (tris(3-sulfophenyl)phosphine trisodium salt), were synthesized from the organometallic precursor [Ni(cod)2] in neat glycerol under hydrogen pressure. NiNPs were fully characterized ((HR)-TEM, EDX, XPS, XRD, IR, magnetization), both at solid state and directly from the corresponding colloidal solutions in glycerol due to its negligible vapour pressure. NiNPs dispersed in glycerol were applied in hydrogenation reactions, in particular in semihydrogenation of alkynes to give (Z)-alkenes under satisfactory conditions (3 bar H2, 1 mol% Ni, 100 °C), showing remarkable activity and selectivity. The catalytic phase was recycled at least ten times without loss of activity, affording in each case metal-free organic products. Other functional groups such as nitro, nitrile and formyl groups were efficiently hydrogenated to the corresponding anilines, benzylamines and benzylalcohols respectively (77–95% yields). (Figure presented.).

C- ARYL GLYCOSID DERIVATIVES, PHARMACEUTICAL COMPOSITION, PREPARATION PROCESS AND USES THEREOF

This invention relates to a kind of C-aryl glycoside derivatives, its pharmaceutical compositions, preparation methods, and uses thereof. The preparation method comprises: method 1: in a solvent, deprotecting the acetyl protecting groups of compound 1-f in the presence of a base; method 2: 1) compound 2-g reacts with via Mitsunobu reaction; 2) deprotecting the acetyl protecting groups of compound 2-f obtained from step 1; method 3: 1) compound 2-g reacts with via nucleophilic substitution reaction; 2) deprotecting the acetyl protecting groups of compound 3-f obtained from step 1. The pharmaceutical composition comprises a kind of C-aryl glycoside derivatives; it's pharmaceutically acceptable salts and/or prodrugs thereof and excipient thereof. This invention further relates to a kind of C-aryl glycoside derivatives, it's pharmaceutically acceptable salts or pharmaceutical compositions thereof for the use in preparation of a SGLT inhibitor. The C-aryl glycoside derivatives of this invention provides a new direction for the study of SGLT inhibitors.

Endo-selective pd-catalyzed silyl methyl heck reaction

A palladium (Pd)-catalyzed endo-selective Heck reaction of iodomethylsilyl ethers of phenols and aliphatic alkenols has been developed. Mechanistic studies reveal that this silyl methyl Heck reaction operates via a hybrid Pd-radical process and that the silicon atom is crucial for the observed endo selectivity. The obtained allylic silyloxycycles were further oxidized into (Z)-alkenyldiols.

Enantioselective allylation of selected ortho-substituted benzaldehydes: A comparative study

We report a systematic study of the allylation of ortho-substituted benzaldehydes under catalysis of a Lewis base (N, Ndioxide), a Lewis acid (Keck allylation), and a Bronsted acid. ortho-Halobenzaldehydes were used as the aldehydic substrates, and specia

Flow Chemistry Syntheses of Styrenes, Unsymmetrical Stilbenes and Branched Aldehydes

Two tandem flow chemistry processes have been developed. A single palladium-catalysed Heck reaction with ethylene gas provides an efficient synthesis for functionalised styrenes. Through further elaboration the catalyst becomes multi-functional and performs a second Heck reaction providing a single continuous process for the synthesis of unsymmetrical stilbenes. In addition, the continuous, rhodium-catalysed, hydroformylation of styrene derivatives with syngas affords branched aldehydes with good selectivity. Incorporation of an in-line aqueous wash and liquid-liquid separation allowed for the ethylene Heck reaction to be telescoped into the hydroformylation step such that a single flow synthesis of branched aldehydes directly from aryl iodides was achieved. The tube-in-tube semi-permeable membrane-based gas reactor and liquid-liquid separator both play an essential role in enabling these telescoped flow processes.