87258-91-1

Basic information

• Product Name: 5-Hexen-2-one, 3-hydroxy-3-phenyl-
• CAS NO: 87258-91-1
• Molecular Formula: C12H14O2
• Molecular Weight: 190.242
• Mol File: 87258-91-1.mol

Chemical Properties

• CAS DataBase Reference: 5-Hexen-2-one, 3-hydroxy-3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Hexen-2-one, 3-hydroxy-3-phenyl-(87258-91-1)
• EPA Substance Registry System: 5-Hexen-2-one, 3-hydroxy-3-phenyl-(87258-91-1)

Safety Data

• Hazardous Substances Data: 87258-91-1(Hazardous Substances Data)

Upstream product

• 98015-24-8 2-(allyloxy)-1-phenylpropan-1-one 
• 87258-88-6 N-allyl-N-(1-benzoylethyl)-N,N-dimethylammonium bromide 
• 762-73-2 trimethyl(allyl)stannane 
• 579-07-7 1-Phenylpropane-1,2-dione 
• 103383-80-8 1-phenyl-2-(pyrrolidin-1-yl)ethane-1,2-dione 
• 917-54-4 methyllithium 
• 762-72-1 allyl-trimethyl-silane 
• 106-95-6 allyl bromide 
• 15351-09-4 metamfepramone 
• 14088-57-4 2-diazo-1-phenyl-1-propanone 
• 65755-81-9 1-phenyl-2-(2-propenyloxy)ethanone 

Relevant articles and documents

Development of a Phase-Transfer-Catalyzed, [2,3]-Wittig Rearrangement

An investigation into the use of phase-transfer catalysis for the [2,3]-sigmatropic rearrangement of allyloxy carbonyl compounds is described. Initial studies focused on identifying viable substrate classes that would undergo selective [2,3]-rearrangement under phase-transfer catalysis. Under certain conditions, the [2,3]-sigmatropic rearrangement of allyloxy carbonyl compounds takes place in the presence of a phase-transfer agent, providing a rare example of a phase-transfer-catalyzed unimolecular reaction. In the course of this investigation, it was found that catalysis is dependent on several variables including base concentration, catalyst structure, and substrate lipophilicity. Preliminary testing of chiral, nonracemic phase-transfer catalysts has shown promising levels of enantioselectivity for future development.

Photo-allylation and photo-benzylation of carbonyl compounds using organotrifluoroborate reagents

Allyl- and benzyl-trifluoroborates can be applied to the photoreaction of carbonyl compounds to afford the corresponding alcoholic adducts in acceptable yields via a photo-induced single electron transfer pathway. The results were confirmed from the react

Remarkable enhancement of photo-allylation of aromatic carbonyl compounds with a hypervalent allylsilicon reagent by donor molecules

Photo-allylation of various aromatic carbonyl compounds with a penta-coordinated allylsiliconate reagent was remarkably accelerated by the addition of a donor molecule. As the oxidation potential of the allylsiliconate was significantly decreased in the p

Indium-mediated allylation of 1,2-diketones

Indium-mediated allylation of 1,2-dicarbonyl compounds with indium and allylic bromides was achieved in the presence of nBu4NI or NH4Cl as additive to afford mono- and/or diallylated products in good yields.

Enantioselective synthesis of α-branched α-hydroxy ketones via chiral N-sulfonyl-2-alkyl-2-cyano-1,3-oxazolidines

The stereochemically homogeneous title compounds 6, prepared with two steps from orthoesters and N-tosyl-phenylglycinol 4, afford with two sequential Grignard additions predominantly the tertiary alcohols 8. Electrochemical detosylation, followed by aqueo

Regioreversed Allylation in Lewis Acid-mediated and Photochemical Addition Reactions of Unsymmetric α-Diketones with Allylic Stannanes

In the photochemical reaction of allyl- and benzyltrimethylstannanes with unsymmetric α-diketones (PhCOCOR), the allylic group was introduced to the benzoyl carbon in high or excellent selectivity, whereas the acyl carbon was allylated either exclusively

Asymmetric Synthesis of Functionalized Tertiary Homoallyl Alcohols by Diastereoselective Allylation of Chiral α-Keto Amides Derived from (S)-Proline Esters. Control of Stereochemistry Based on Saturated Coordination of Lewis Acid

Diastereoselective additions of allylsilanes and -stannanes to chiral α-keto amides 1a-c derived from esters of (S)-proline in the persence of Lewis acids afforded optically active tertiary homoallyl alcohols of high diastereomeric excesses (up to 92percent de).Reaction conditions were examined in detail.The order of the effectiveness of Lewis acids on diastereoselectivity was SnBr4 > SnCl4 > TiCl4 > BF3*OEt2 >> AlCl3.At least 3 mol equiv of SnCl4 were required to achieve the high diastereoselection.The coordination of Lewis acids with the oxygen atom(s) of 1 may be one of the resonans for the high diastereoselectivity.When SnCl4 as used, dichloromethane was the best solvent.In the case of TiCl4, a heterogeneous reaction mixture in n-hexane and CH2Cl2 led to higher diastereoselectivity than a homogeneous solution in CH2Cl2 alone.Both allylsilane and -stannane led to homoallyl alcohols of predominant R configuration.The reaction was faster with allylstannane than with allylsilane.Allylation with allylmagnesium bromide showed the opposite diastereoselectivity.From a study of the effect of temperature, the enthalpy factor was found to be more important than the entropy factor.Some of the diastereomers (3a,b) were found to cyclize spontaneously to afford the corresponding lactones (5a,b).This lactonization process was highly stereoselective.Compounds 5a,b were separed from 4a,b, respectively, by preparative TLC.Removal of the chiral auxiliaries by methyllithium afforded essentially enantiomerically pure acyloins (6 and 9) (>98percent ee) of both enantiomers.

Base Catalysed Rearrangements involving Ylide Intermediates. Part 18. Competing , , and Rearrangements of Ammonium Ylides

The rearrangements of acyl stabilised ammonium ylides are, in several cases, accompanied by competing rearrangements and in one case by a rearrangement.For examples involving migrating benzyl or phenylethyl groups the mechanism of these rearrangements has been studied.Thus the competing , , and rearrangements of the ylide (12) are largely intramolecular, but the intermolecularity is as high as 28percent for the and rearrangements and 14percent for the rearrangement in methanol at 55 deg C.The competing and rearrangements of the optically active (29a) give products with predominant retention of the configuration of the migrating phenylethyl group, but the intramolecular stereoselectivity of the rearrangement is significantly greater than that of the rearrangement.These results are consistent with a radical pair pathway for all three modes of rearrangement.Suitably substituted acyl stabilised allylammonium ylides (55) rearrange by competing , and processes.