1323308-07-1

Basic information

• Product Name: (E)-phenyl(2-styrylphenyl)methanol
• Synonyms: (E)-phenyl(2-styrylphenyl)methanol
• CAS NO: 1323308-07-1
• Molecular Weight: 286.373
• Mol File: 1323308-07-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (E)-phenyl(2-styrylphenyl)methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-phenyl(2-styrylphenyl)methanol(1323308-07-1)
• EPA Substance Registry System: (E)-phenyl(2-styrylphenyl)methanol(1323308-07-1)

Safety Data

• Hazardous Substances Data: 1323308-07-1(Hazardous Substances Data)

Upstream product

• 100-42-5 styrene 
• 119-61-9 benzophenone 
• 6630-33-7 ortho-bromobenzaldehyde 
• 52095-44-0 (E)-2-styrylbenzaldehyde 
• 100-58-3 phenylmagnesium bromide 
• 591-51-5 phenyllithium 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 78602-28-5 1-bromo-2-(2-phenylethenyl)benzene 
• 100-52-7 benzaldehyde 

Downstream Products

• 5324-00-5 2,3-diphenyl-1H-indene 
• 18636-54-9 1,2-diphenyl-1H-indene 
• 22256-19-5 trans-1,2-diphenyl-2,3-dihydro-1H-indene 
• 7474-64-8 2,3-diphenyl-indan-1-one 
• 18636-54-9 1,2-Diphenyl-inden 

Relevant articles and documents

Manganese-Catalyzed Redox-Neutral C?H Olefination of Ketones with Unactivated Alkenes

Since 1987, stoichiometric cyclomanganation of ketones and subsequent reactions with olefins in the presence of either palladium salts or trimethylamine N-oxide (Me3N+O?) have been reported, but the catalytic versions remain untouched so far. Herein, the first manganese-catalyzed redox-neutral C?H olefination of ketones with unactivated alkenes is described, and shows a distinct reactivity with its parent stoichimetric reactions. Remarkably, mechanistic experiments and DFT calculations uncovers a unique concerted bis-metalation deprotonation (CBMD) mechanism of the Mn-Zn-enabled C?H bond activation.

Selective Divergent Synthesis of Indanols, Indanones, and Indenes via Acid-Mediated Cyclization of (Z)- and (E)-(2-Stilbenyl)methanols and Its Application for the Synthesis of Paucifloral F Derivatives

Starting from bromo/iodobenzaldehyde derivatives, the corresponding (Z)- and (E)-(2-stilbenyl)methanols could be prepared in 2-5 steps via Pd-catalyzed cross-coupling reactions (Sonogashira and Heck reactions) followed by aryllithium/aryl Grignard addition. For the (E)-stilbenes, subsequent acid-mediated cyclization using p-TsOH immobilized on silica (PTS-Si) at low temperatures furnished the 2,3-trans-1-indanols with complete stereocontrol at the C2-C3. Further oxidization of the alcohol provided the indanones, which are structurally related to the natural product paucifloral F. At higher temperatures, 1,2- and 2,3-disubstituted indenes could be selectively prepared in good to excellent yields. On the other hand, the (Z)-stilbenes, under similar conditions (PTS-Si), did not give the indanols; only the 1,2-disubstituted indenes could be obtained. To gain further insights into the stereochemistry at C2-C3 for the (Z)-stilbenes, hydride or azide was employed as a nucleophile; the corresponding indane products were obtained with the cis stereochemistry at the C2-C3. Thus, the (Z)- or (E)-olefin geometry of the substrate directed the stereoselective indanyl cyclization to furnish the cis or trans at the C2-C3 ring junction, respectively, while reaction conditions controlled the selectivity of the product types.

Photochemical studies on aromatic γ,δ-epoxy ketones: Efficient synthesis of benzocyclobutanones and indanones

Irradiation of terminal aromatic γ,δ-epoxy ketones with a 450 W UV lamp led to Norrish type II cyclization/semi-pinacol rearrangement cascade reaction which formed the benzocyclobutanones containing a full-carbon quaternary center, whereas irradiation of substituted aromatic γ,δ-epoxy ketones led to the indanones through a photochemical epoxy rearrangement and 1,5-biradicals cyclization tandem reaction.