156927-76-3

Basic information

• Product Name: (S)-1-phenyl-1-methoxyprop-2-ene
• Synonyms: (S)-1-phenyl-1-methoxyprop-2-ene
• CAS NO: 156927-76-3
• Molecular Weight: 148.205
• Mol File: 156927-76-3.mol

Chemical Properties

• CAS DataBase Reference: (S)-1-phenyl-1-methoxyprop-2-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-phenyl-1-methoxyprop-2-ene(156927-76-3)
• EPA Substance Registry System: (S)-1-phenyl-1-methoxyprop-2-ene(156927-76-3)

Safety Data

• Hazardous Substances Data: 156927-76-3(Hazardous Substances Data)

Upstream product

• 128806-31-5 (S)-1-(2,4-Dinitro-phenyl)-pyrrolidine-2-carboxylic acid [2'-(2-methoxy-1-methyl-2-phenyl-ethylselanyl)-[1,1']binaphthalenyl-2-yl]-amide 
• 67-56-1 methanol 
• 873-66-5 1-propenylbenzene 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 87802-71-9 (E)-methyl cinnamyl carbonate 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 444575-79-5 carbonic acid 1,1-dimethylethyl 1-phenyl-2-propenyl ester 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 438497-34-8 1-methoxy-2-[(1S,2R)-2-methoxy-1-methyl-2-phenylethyl]seleno-3-[(1S)-1-(methylthio)ethyl]benzene 

Downstream Products

• 121194-48-7 (2S,3R)-3-Methoxy-3-phenyl-1,2-propanediol 

Relevant articles and documents

Time-dependent enantiodivergent synthesis via sequential kinetic resolution

The preparation of both enantiomers of chiral molecules is among the most fundamental tasks in organic synthesis, medicinal chemistry and materials science. Achieving this goal typically requires reversing the absolute configuration of the chiral component employed in the reaction system that is being used. The task becomes challenging when the natural source of the chiral component is not available in both configurations. Herein, we report a time-dependent enantiodivergent synthesis, in which an Ir-catalysed allylic substitution reaction uses one catalyst sequentially to promote two kinetic resolution reactions, enabling the synthesis of both enantiomers of the product using the same enantiomer of a chiral catalyst. The appropriate permutation of individual reaction rates is essential for the isolation of the chiral products in opposite configurations with high enantiopurity when quenched at different reaction times. This work provides an alternative solution for the preparation of both enantiomers of chiral molecules. [Figure not available: see fulltext.].

Catalytic asymmetric oxyselenenylation-elimination reactions using chiral selenium compounds

Only catalytic amounts of chiral selenium reagents are necessary to achieve a sequence of methoxyselenenylation and oxidative β-hydride elimination of alkenes. Performing this reaction with peroxodisulfates and various metal salts led to enantiomeric excesses of up to 75%.

Regio- and Enantioselective Allylation of Phenols via Decarboxylative Allylic Etherification of Allyl Aryl Carbonates Catalyzed by (Cyclopentadienyl)ruthenium(II) Complexes and Pyridine-Hydrazone Ligands

(Cyclopentadienyl)tris(acetonitrile)ruthenium hexafluorophosphate [CpRu(CH3CN)3][PF6] in combination with pyridine-hydrazone ligands efficiently catalyzes the asymmetric decarboxylative allylic rearrangement of allyl aryl carbonates. Formation of C-O bonds with high regio- and enantioselectivity ratios (up to 95:5 and 98% ee) is obtained. Good stereocontrol of the pseudotetrahedral geometry of the CpRu moiety is achieved by the hydrazone ligand and its "electron-poor" nature is evidenced through the epimerization of the hexacoordinated TRISPHAT-N anion.

Enantioselective allylic etherification: Selective coupling of two unactivated alcohols

An Ir(P,alkene) complex catalyzes the enantioselective allylic etherification of unactivated secondary allylic alcohols. Useful levels of enantioselectivity and yield were achieved with this operationally easy and robust protocol. Initial kinetic studies indicate a significant rate difference for the substrate enantiomers, allowing for a resolution process. cod=1,5-cyclooctadiene Copyright

(Cyclopentadienyl)ruthenium-catalyzed regio- and enantioselective decarboxylative allylic etherification of allyl aryl and alkyl carbonates

(Cyclopentadienyl)tris(acetonitrile)ruthenium hexafluorophosphate {[CpRu(NCMe)3][PF6] or (cyclopentadienyl) (I·6-naphthalene)ruthenium hexafluorophosphate {[CpRu(I·6-naphthalene)][PF6]} in combination with a pyridine oxazoline ligand efficiently catalyze the decarboxylative allylic rearrangement of allyl aryl carbonates. Good levels of regio- and enantioselectivity are obtained. Starting from enantioenriched secondary carbonates, the reaction is stereospecific and the corresponding allylic ethers are obtained with net retention of configuration. An intermolecular version of this transformation was also developed using allyl alkyl carbonates as substrates. Conditions were found to obtain the corresponding products with similar selectivity as in the intramolecular process. Through the use of a hemi-labile hexacoordinated phosphate counterion, a zwitterionic air- and moisture-stable chiral ruthenium complex was synthesized and used in the enantioselective etherification reactions. This highly lipophilic metal complex can be recovered and efficiently reused in subsequent catalysis runs. Copyright

Regio- and enantioselective O-allylation of phenol and alcohol catalyzed by a planar-chiral cyclopentadienyl ruthenium complex

(Chemical Equation Presented) Design of an asymmetric catalyst: The planar-chiral cyclopentadienyl ruthenium complex shown in the scheme effectively catalyzes the reactions of unsymmetrically substituted allyl halides with phenol and alcohol to give the corresponding branched allyl ethers with high regio- and enantioselectivity.

Preparation of a new chiral non-racemic sulfur-containing diselenide and applications in asymmetric synthesis

The synthesis of the new chiral non-racemic sulfur-containing diselenide, di-2-methoxy-6-[(1S)-1-(methylthio)ethyl]phenyl diselenide, is described. When treated with ammonium persulfate this diselenide is transformed into the corresponding selenenyl sulfate, which acts as a strong electrophilic reagent and adds to alkenes, in the presence of methanol or water, to afford the products of selenomethoxylation or selenohydroxylation, respectively, with excellent diastereoselectivities. Starting from alkenes containing internal nucleophiles, asymmetric cyclofunctionalization reactions also resulted in good chemical yields, complete regioselectivities, and high diastereoselectivities. This sulfur-containing diselenide can also be used in catalytic amounts to promote one-pot selenenylation-deselenenylation processes, from which several types of products can be obtained in high yield and with good enantiomeric excess.

Asymmetric Methoxyselenenylation of Alkenes with Chiral Ferrocenylselenium Reagents

Asymmetric methoxyselenenylation of alkenes was studied using some chiral ferrocenylselenium compounds which were prepared from chiral ferrocenyl-substituted amine, sulfoxide, oxazoline, and pyrrolidine. The highest diastereoselectivity was observed using the chiral amino-substituted ferrocenylserenium triflates in the reaction with trans-β-methylstyrene in an excellent yield. The reaction with silyl enol ethers gave chiral α-seleno ketone with moderate to excellent selectivities. The β,γ-unsaturated ester may be converted into the optically active γ-alkoxy α,β-unsaturated ester using ammonium persulfate in the presence of a catalytic amount of the chiral diferrocenyl diselenide in low optical yields.

ASYMMETRIC TRANS-ADDITION REACTIONS USING CHIRAL SELENOBINAPHTHYLS

Asymmetric trans-addition reactions of (E)-phenylpropene, a mechanistically novel reaction, have been achieved by using chiral selenium-containing binaphthyl derivatives.Introduction of an amide group at 2'-position in the binaphthyl skeleton enhances considerably the diastereomeric excess (d.e.) of the asymmetric reaction presumably due to attractive interaction between the nitrogen lone pair and the seleniranium intermediate.Introduction of another chiral center in the amide group further enhances the d.e. as high as 79 percent, which is the highest asymmetric induction ever achieved in the asymmetric trans-addition reaction.