13632-62-7

Usage

Structure

A phenyl group attached to a propargyl alcohol moiety, with a methoxy group located on the phenyl ring.

Composition

Carbon (C), Hydrogen (H), and Oxygen (O) atoms

Molecular Weight

238.29 g/mol (calculated based on the chemical formula)

Functional Groups

Phenyl, propargyl alcohol, and methoxy groups

Physical State

Likely a solid or a liquid at room temperature (not specified in the material)

Applications

a. Organic synthesis
b. Formation of pharmaceuticals and agrochemicals
c. Reagent in the preparation of other organic compounds
d. Potential applications in materials science

Biological Properties

a. Anti-inflammatory
b. Anti-cancer

Field of Interest

Medicinal chemistry and drug discovery

Upstream product

• 611-94-9 4-Methoxybenzophenone 
• 74-86-2 acetylene 
• 1369584-53-1 C₁₉H₂₂O₂Si 
• 4301-14-8 acetylenemagnesium bromide 

Downstream Products

• 13632-74-1 1,4-bis-(4-methoxy-phenyl)-1,4-diphenyl-but-2-yne-1,4-diol 
• 120548-41-6 4-[4-(3-nitro-phenyl)-1,4-diphenyl-butatrienyl]-anisole 
• 119852-63-0 4-[4-(4-nitro-phenyl)-1,4-diphenyl-butatrienyl]-anisole 
• 20921-53-3 N-Cyclohexyl-carbaminsaeure-<3-(p-methoxy-phenyl)-3-phenyl-propin-(1)-yl-(3)>-ester 
• 1257403-40-9 ethyl 2-(4-methoxyphenyl)-2-phenyl-2H-naphtho[1,2-b]pyran-5-carboxylate 
• 1267600-38-3 10-(4-methoxyphenyl)-5,10-diphenylbenzo-[de]pyrano[2,3-g]isoquinoline-4,6(5H,10H)-dione 
• 1267600-37-2 5-butyl-10-(4-methoxyphenyl)-10-phenylbenzo-[de]pyrano[2,3-g]isoquinoline-4,6(5H,10H)-dione 
• 1408444-26-7 benzyl 2-(3-hydroxy-3-(4-methoxyphenyl)-3-phenylprop-1-yn-1-yl)benzoate 
• 1606139-20-1 C₂₅H₂₃NO₄S 
• 120555-67-1 (Z)-β-(4-methoxyphenyl)cinnamic aldehyde 
• 120553-80-2 (E)-β-(4-methoxyphenyl)cinnamic aldehyde 

Relevant academic research and scientific papers

Synthesis and photochromic behaviour of a series of benzopyrans bearing an: N -phenyl-carbazole moiety: Photochromism control by the steric effect

Five new N-phenyl-carbazole benzopyrans bearing different substitutions on one of the phenyl rings at the sp3 carbon have been synthesized. Their molecular structures were investigated by X-ray and NMR analyses and through quantum chemical calculations. T

Synthesis, Characterization, and Reactivity of Cationic Gold Diarylallenylidene Complexes

Methoxide abstraction from gold acetylide complexes of the form (L)Au[η1-C≡CC(OMe)ArAr′] (L=IPr, P(tBu)2(ortho-biphenyl); Ar/Ar′=C6H4X where X=H, Cl, Me, OMe) with trimethylsilyl trifluoromethanesulfonate (TMSOTf) at ?78 °C resulted in the formation of the corresponding cationic gold diarylallenylidene complexes [(L)Au=C=C=CArAr′]+ OTf? in ≥85±5 % yield according to 1H NMR analysis. 13C NMR and IR spectroscopic analysis of these complexes established the arene-dependent delocalization of positive charge on both the C1 and C3 allenylidene carbon atoms. The diphenylallenylidene complex [(IPr)Au=C=C=CPh2]+ OTf? reacted with heteroatom nucleophiles at the allenylidene C1 and/or C3 carbon atom.

Metal- and Acid-Free Methyl Triflate Catalyzed Meyer-Schuster Rearrangement

A novel metal- and acid-free preparation of synthetically useful α,β-unsaturated carbonyl compounds from propargyl alcohols has been realized. This Meyer-Schuster rearrangement process is effectively catalyzed by methyl triflate (20 mol%) to prepare a broad scope of conjugated E -enals and E -enones generally in good to excellent yields (up to 90%). This reaction procedure operates under mild conditions (70 °C), in air, with short reaction times (1 h). Moreover, a carbocation intermediate trapped by the solvent 2,2,2-trifluoroethanol was isolated during this transformation.

Synthesis of Organophosphorus Compounds through Copper-Catalyzed Annulation Involving C-O and C-P Bond Formations

A novel copper(II) trifluoromethanesulfonate-catalyzed, high-efficiency, and atom-economical synthesis of valuable organophosphorus compounds via cascade annulation of propargylic alcohols with diphenylphosphine oxide is described. This protocol, which has a good functional-group compatibility and insensitivity to an ambient atmosphere, provides a simple and direct pathway to the products, organophosphorus compounds, in good yields under mild conditions. The method could be efficiently scaled up to gram scale, thus highlighting a potential application of this methodology.

Complementary iron(II)-catalyzed oxidative transformations of allenes with different oxidants

Substituent- and oxidant-dependent transformations of allenes are described. Given the profound influence of the substituent on the reactivity of allenes, the subtle differences in allene structures are manifested in the formation of diverse products when reacted with different electrophiles/oxidants. In general, reactions of nonsilylated allenes involve an allylic cation intermediate by forming a C-O bond, at the sp-hybridized C2, with either DDQ (2,3-dichloro-5,6-dicyano-p-benzoquinone) or TBHP (tert-butyl hydroperoxide), along with FeCl2·4 H2O (10 mol %). In contrast, silylated allenes favor the formation of propargylic cation intermediates by transferring the allenic hydride to the oxidant, thus generating 1,3-enynes (E1 product) or propargylic THBP ethers (SN1 product). The formation of these different putative cationic intermediates from nonsilylated and silylated allenes is strongly supported by DFT calculations. Profound impact: Iron(II)-catalyzed transformations of allenes induced by either DDQ or tBuOOH depend on the substituent on the allenes. Nonsilylated and silylated allenes show complementary reactivity upon exposure to DDQ and tBuOOH in the presence of an iron(II) catalyst. Nonsilylated allenes incorporate the oxidant at the sp-hybridized carbon, whereas the silylated allenes generate 1,4-dehydrogenated 1,3-enynes. DDQ=2,3-dichloro-5,6-dicyano-1,4-benzoquinone.

Convenient and highly efficient routes to 2 H-chromene and 4-chromanone derivatives: Iodine-promoted and p-toluenesulfonic acid catalyzed cascade cyclizations of propynols

A convenient strategy is presented for the easy preparation of a series of 2 H-chromenes under mild conditions through iodocyclization of readily accessible propynols. In addition, various 4-chromanones can be synthesized through a p-toluenesulfonic acid catalyzed cascade cyclization with high efficiency (yields up to 99%). Our developed reaction systems are proven to have good functional-group applicability and can be scaled up to gram quantities in satisfactory yields. These systems also provide a new synthetic strategy for two types of important flavonoid skeleton without using costly and toxic metal catalysts. Additionally, the resulting halides could be further exploited in subsequent palladium-catalyzed coupling reactions, so these compounds could act as potential intermediates for the construction of some valuable drug molecules.

The influence of a 1,1-diarylvinyl moiety on the photochromism of naphthopyrans

1,1,3-Triarylpent-4-en-1-yn-3-ols, efficiently obtained in two steps from 1,1,3-triarylprop-2-yn-1-ols by a Meyer-Schuster rearrangement and subsequent addition of lithium trimethylsilylacetylide, react with either a 1- or 2- naphthol to afford photochrom