4435-52-3

Usage

Physical state

Colorless to pale yellow liquid

Solubility

Insoluble in water, soluble in organic solvents

Uses

a. Fragrance ingredient in perfumes
b. Chemical intermediate in the synthesis of other organic compounds

Preparation method

Reduction of 1,3-diphenylbutan-1-one with reducing agents such as sodium borohydride or lithium aluminum hydride

Odor

Mild, sweet

Toxicity

Low toxicity

Upstream product

• 98-85-1 1-Phenylethanol 
• 855280-58-9 1-acetoxy-1,3-diphenylbutane 
• 98-86-2 acetophenone 
• 100-51-6 benzyl alcohol 
• 947597-52-6 (C₅H₅)2ZrClCH₂CHCH₃C₆H₅ 
• 100-52-7 benzaldehyde 
• 495-45-4 dypnone 
• 20698-95-7 (3S)-1,3-diphenylbutan-1-one 
• 35660-91-4 (E)-1-phenyl-2-buten-1-one 
• 98-80-6 phenylboronic acid 
• 64-17-5 ethanol 
• 91-01-0 1,1-Diphenylmethanol 
• 1445-91-6 (S)-1-phenylethanol 
• 54435-79-9 (E)-1,3-diphenyl-3-methyl-2-propen-1-one 

Downstream Products

• 7614-93-9 1,3-diphenyl-1-butene 
• 1533-20-6 1,3-diphenylbutane-1-one 
• 102592-75-6 4-nitro-benzoic acid-(1,3-diphenyl-butyl ester) 

Relevant academic research and scientific papers

Compartmentalization and Photoregulating Pathways for Incompatible Tandem Catalysis

This contribution describes an advanced compartmentalized micellar nanoreactor that possesses a reversible photoresponsive feature and its application toward photoregulating reaction pathways for incompatible tandem catalysis under aqueous conditions. The

Chromium-Catalyzed Linear-Selective Alkylation of Aldehydes with Alkenes

We developed a chromium-catalyzed, photochemical, and linear-selective alkylation of aldehydes with alkylzirconium species generated in situ from a wide range of alkenes and Schwartz's reagent. Photochemical homolysis of the C-Zr bond afforded alkyl radicals, which were then trapped by a chromium complex catalyst to generate the alkylchromium(III) species for polar addition to aldehydes. The reaction proceeded with high functional group tolerance at ambient temperature under visible-light irradiation.

Double Asymmetric Hydrogenation of Linear β,β-Disubstituted α,β-Unsaturated Ketones into γ-Substituted Secondary Alcohols using a Dual Catalytic System

Double asymmetric hydrogenation of linear β,β-disubstituted α,β-unsaturated ketones catalyzed by the DM-SEGPHOS/DMAPEN/RuII complex with t-C4H9OK afforded the γ-substituted secondary alcohols in high diastereo- and enantioselectivities. Some mechanistic experiments suggested that two different reactive species, type (I) and (II), were reversibly formed in this catalytic system: Type (I) with the diamine ligand DMAPEN enantioselectively hydrogenated the enones into the chiral allylic alcohols, and type (II) without the diamine ligand diastereoselectively hydrogenated the allylic alcohols into the γ-substituted secondary alcohols. This dual catalysis protocol was successfully applied to the reaction of a variety of aliphatic- and aromatic-substituted enone substrates.

Aldehyde-catalyzed transition metal-free dehydrative β-alkylation of methyl carbinols with alcohols

Different to the borrowing hydrogen strategy in which alcohols were activated by transition metal-catalyzed anaerobic dehydrogenation, the direct addition of aldehydes was found to be an effective but simpler way of alcohol activation that can lead to efficient and green aldehyde-catalyzed transition metal-free dehydrative C-alkylation of methyl carbinols with alcohols. Mechanistic studies revealed that the reaction proceeds via in situ formation of ketones by Oppenauer oxidation of the methyl carbinols by external aldehydes, aldol condensation, and Meerwein-Ponndorf-Verley (MPV)-type reduction of α,β-unsatutated ketones by substrate alcohols, affording the useful long chain alcohols and generating aldehydes and ketones as the by-products that will be recovered in the next condensation to finish the catalytic cycle. Copyright

Dehydrogenation of alcohols by bis(phosphinite) benzene based and bis(phosphine) ruthenocene based iridium pincer complexes

Dehydrogenation of alcohols by three iridium pincer complexes, IrH(Cl)[2,6-(tBu2PO)2C6H 3] (1), {IrH(acetone)[2,6-(tBu2PO) 2C6H3]}{BF4} (2), and IrH(Cl)[{2,5-(tBu2PCH2)2C 5H2}Ru(C5H5)] (3), is reported, in both the presence and the absence of a sacrificial hydrogen acceptor. Dehydrogenation of secondary alcohols proceeds in a catalytic mode with turnover numbers up to 3420 (85% conversion) for acceptorless dehydrogenation of 1-phenylethanol. Primary alcohols are readily decarbonylated even at room temperature to give catalytically inactive 16e Ir-CO adducts. The mechanism of this transformation was studied in detail, especially for EtOH; new intermediates were isolated and characterized.

Palladium-catalysed transfer hydrogenation of aromatic nitro compounds - An unusual chain elongation

Aromatic nitro compounds are reduced via transfer hydrogenation in the presence of palladium on magnesium-lanthanum mixed oxide support in ethanol yielding the corresponding amines. With several acetophenone derivatives, the reduction was accompanied by c

Cross-coupling reaction of alcohols for carbon-carbon bond formation using pincer-type NHC/palladium catalysts

A cross-coupling reaction of different alcohols was achieved using a pincer-type NHC/PdBr complex as the catalyst precursor, and the reaction, under either Ar or H2 gas, displayed a broad substrate scope with respect to both primary and secondary alcohol components, with high alcohol product selectivity. The Royal Society of Chemistry 2010.

Rh(I)/diene-catalyzed addition reactions of aryl/alkenylboronic acids with aldehydes

[Rh(COD)Cl]2-catalyzed addition reactions of arylboronic acids with aldehydes, with low Rh(I) catalyst loading, are described. We also found that the reaction of arylboronic acids with α,β-unsaturated aldehydes greatly depends on the solvent and the steric hindrance of the reagents/substrates.

Highly chemo- And enantioselective hydrogenation of linear α,β-unsaturated ketones

A study was conducted to report the synthesis of sulfoximine-derived P,N-ligands and their applications in indium-catalyzed asymmetric hydrogenation reactions. Investigations were conducted using linear β,β- disubstituted 1,3-diphenyl-2-butenone as model substrate and iridium, having a ketonic phenyl group and two alkyl substituents at the olefinic β-positions. Methyl ketone with β-methyl and β-phenyl substituent was also applied in the investigations.

Orthoplatinated triarylphosphite as a highly efficient catalyst for addition reactions of arylboronic acids with aldehydes: Low catalyst loading catalysis and a new tandem reaction sequence

(Chemical Equation Presented) Readily available, air/moisture-stable orthoplatinated triarylphosphite catalyzes the addition reactions of arylboronic acids with aldehydes with the catalyst loading as low as 0.01%. It also cataylzes a new tandem reaction of arylboronic acids with α,β- unsaturated aldehydes to form 1,3-diaryl-1-propanols. Our study provides a new paradigm for the application of orthoplatinated triarylphosphites, and may pave the road to develop other Pt(II) catalysts for such addition reactions and other tandem reactions with such addition reactions as part of the reaction sequence.