27927-59-9

Basic information

• Product Name: 1-Pentanone,4-hydroxy-1-phenyl-
• Synonyms: Valerophenone,4-hydroxy- (8CI)
• CAS NO: 27927-59-9
• Molecular Formula: C11H14 O2
• Molecular Weight: 178.231
• Mol File: 27927-59-9.mol

Chemical Properties

• CAS DataBase Reference: 1-Pentanone,4-hydroxy-1-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pentanone,4-hydroxy-1-phenyl-(27927-59-9)
• EPA Substance Registry System: 1-Pentanone,4-hydroxy-1-phenyl-(27927-59-9)

Safety Data

• Hazardous Substances Data: 27927-59-9(Hazardous Substances Data)

Upstream product

• 583-05-1 1-phenylpentane-1,4-dione 
• 64-17-5 ethanol 
• 768-03-6 Phenyl vinyl ketone 
• 132205-09-5 (1R*,2Z,4S*)/(1R*,2Z,4R*)-1-Phenyl-2-pentene-1,4-diol 
• 1228681-29-5 1-phenyl-2-pentene-1,4-diol 
• 89968-81-0 1-Phenylpentane-1,4-diol 
• 1713-41-3 trans-1-Phenyl-2-methylcyclobutanol 
• 98-88-4 benzoyl chloride 
• 861399-10-2 (RS)-1-(n-butyltellanyl)-3-butanol 
• 16330-23-7 1-phenyl-1-pentyn-4-ol 
• 613-91-2 acetophenone oxime 
• 1008-76-0 4,5-dihydro-5-phenyl-2(3H)-furanone 
• 98-86-2 acetophenone 
• 75-56-9 methyloxirane 

Downstream Products

• 164113-08-0 2-ethylthio-2-methyl-5-phenyltetrahydrofuran 
• 4457-59-4 (2R*,5S*)-2-methyl-5-phenyltetrahydrofuran 
• 2235-83-8 5-phenyl-2-pentanone 
• 583-05-1 1-phenylpentane-1,4-dione 

Relevant articles and documents

Identification of Bond-Weakening Spirosilane Catalyst for Photoredox α-C?H Alkylation of Alcohols

The development of catalyst-controlled site-selective C(sp3)?H functionalization is a current major challenge in organic synthesis. This paper describes DFT-guided identification of pentavalent silicate species as a novel bond-weakening catalyst for the α-C?H bonds of alcohols together with a photoredox catalyst and a hydrogen atom transfer catalyst. Specifically, Martin's spirosilane accelerated α-C?H alkylation of alcohols. (Figure presented.).

Nonclassical Mechanism in the Cyclodehydration of Diols Catalyzed by a Bifunctional Iridium Complex

1,4- and 1,5-diols undergo cyclodehydration upon treatment with cationic N-heterocyclic carbene (NHC)–IrIII complexes to give tetrahydrofurans and tetrahydropyrans, respectively. The mechanism was investigated, and a metal-hydride-driven pathway was proposed for all substrates, except for very electron-rich ones. This contrasts with the well-established classical pathways that involve nucleophilic substitution.

Mutual Cooperation in the Formal Allyl Alcohol Nucleophilic Substitution and Hydration of Alkynes for the Construction of γ-Substituted Ketones

Mutual cooperation in the formal allyl alcohol nucleophilic substitution reaction and hydration of an alkyne has been utilized in the presence of a gold catalyst to give a series of γ-functionalized ketones with high to excellent yields. This reaction actually involved an intramolecular O-H insertion cyclization of an alkyne to form the dihydrofuran intermediate, which was followed by the nucleophilic addition ring-opening of a dihydrofuran to give the target compound.

A facile preparation of tetralins from arene-1,4-diones using titanium(IV) chloride and triethylsilane

A facile method for the synthesis of tetralins has been described which uses various substituted phenylpentane-1,4-diones as starting material with a combination of TiCl4/Et3SiH. The synthesis involves three reactions under mild conditions. A mechanism has been proposed for the reductive cyclization through ionic hydrogenation, and titanium(IV) chloride catalyzed cyclization.

Phenyliodine diacetate-mediated oxidative cleavage of cyclobutanols leading to γ-hydroxy ketones

Oxidative cleavage of cyclobutanols using PIDA, which leads to efficient entry of γ-hydroxy ketones, is described. When using 2-substituted cyclobutanols, γ-substituted γ-hydroxy ketones are obtained through regioselective C-C bond cleavage.

Functionalized organozincates and organocuprates derived from γ-hydroxytellurides in the preparation of 1,4-hydroxyketones

A C-O-dianionic zincate was generated by a Te/Li exchange reaction of an alkyltelluride, followed by Li/Zn transmetallation and reaction with methyllithium. The reaction between the enantiomerically pure (99% ee) (R)-dianionic zincate and benzoyl chloride

TMSOTf-promoted addition of alkynes to aldehydes: A novel synthesis of chroman-4-ones

A novel synthetic method to prepare chalcones 2 and chroman-4-ones 3 by TMSOTf-promoted addition of alkynes 1 to various aldehydes has been developed. The ratios of chalcones 2, chroman-4-ones 3 and hydrated products 4 varied depending upon the substituents R (nBu, phenyl, H and TMS) on the alkynes 1. We also describe the transformation of the chalcones 2 to the corresponding chroman-4-ones 3 under basic conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Yttrium triflate-catalyzed addition of lithium enolates to 1,2-epoxides. Efficient synthesis of γ-hydroxy ketones

A simple, efficient method is described for the synthesis of γ-hydroxy ketones by the direct opening of 1,2-epoxides with lithium enolates derived from simple ketones in anhydrous toluene, in the presence of Y(OTf)3.

Mechanism of the Rearrangement of 2-(Vinyloxy)alkyl to 4-Ketobutyl Radicals

The rearrangement of 2-(vinyloxy)alkyl to 4-ketobutyl radicals has been demonstrated to proceed by a two step mechanism involving initial 5-endo-trigonal cyclization to give a tetrahydrofuranyl radical which then fragments to the final radical.Fragmentation of the tetrahydrofuranyl radicals is demonstrated by their generation from the corresponding 2-(ethylthio)-tetrahydrofurans with stannanes and AIBN.The rearrangement reaction is completely blocked when the intermediate tetrahydrofuranyl radical is set up to undergo a 5-hexenyl rearrangement.