5208-89-9

Usage

Physical state

Colorless liquid

Odor

Sweet, floral

Uses

a. Flavor and fragrance additive in perfumes and food flavorings
b. Production of pharmaceuticals
c. Precursor in organic synthesis

Health hazards

Potential health risks; proper safety measures should be taken when handling

Safety considerations

Handle with care and follow safety guidelines to minimize exposure and potential health risks

Upstream product

• 1826-67-1 vinyl magnesium bromide 
• 104-55-2 3-phenyl-propenal 
• 14371-10-9 (E)-3-phenylpropenal 
• 14604-31-0 (E)-1-phenylpent-1-en-4-yn-3-ol 
• 593-60-2 Vinyl bromide 
• 108-86-1 bromobenzene 
• 922-65-6 divinylcarbinol 
• 2768-02-7 (vinyl)trimethoxylsilane 

Downstream Products

• 1215019-99-0 C₁₉H₁₉NO₄S 
• 3152-68-9 1-phenyl-pent-1-en-3-one 
• 132592-42-8 (E)-1-phenyl-1,4-pentadien-3-yl 2,2-dimethylpropanoate 
• 615547-08-5 2-((E)-Hexa-3,5-dienyl)-2-((2E,4E)-5-phenyl-penta-2,4-dienyl)-malonic acid bis-(2,2,2-trifluoro-ethyl) ester 
• 687638-55-7 [(E)-1-phenylpenta-1,4-dien-3-yloxy](tert-butyl)dimethylsilane 
• 3152-68-9 (1E)-1-phenylpent-1-en-3-one 
• 35376-41-1 5-phenylcyclohex-2-en-1-one 
• 73291-51-7 (E)-1-phenylpenta-1,4-dien-3-one 
• 117894-26-5 (S)-(+)-5-phenyl-2-cyclohexen-1-one 

Relevant academic research and scientific papers

Iridium-Catalyzed Asymmetric Allylic Alkylation of Deconjugated Butyrolactams

Compared with the ever-growing list of nonprochiral nucleophiles in Ir-catalyzed asymmetric allylic substitution reactions, prochiral nucleophiles are less studied. We present a new prochiral nucleophile, namely, deconjugated butyrolactam, for Ir-catalyze

Enantio- and Diastereodivergent Synthesis of Spirocycles through Dual-Metal-Catalyzed [3+2] Annulation of 2-Vinyloxiranes with Nucleophilic Dipoles

The development of efficient and straightforward methods for obtaining all optically active isomers of structurally rigid spirocycles from readily available starting materials is of great value in drug discovery and chiral ligand development. However, the

Counteranion-controlled regioselectivity in palladium-catalyzed allylic amination of dienyl allylic carbonates

A regioselective Pd-catalyzed allylic amination reaction of dienyl allylic carbonates and aromatic amines has been developed by means of phosphoramidite-palladium catalysis. The regioselectivity could be altered by the counterion of the π-allylpalladium intermediate. As a result, either branched Z-dienyl allylic amines or linear conjugated allylic amines were generated in high levels of regioselectivity from the same substrates by tuning the reaction conditions.

Stereoselective Synthesis of Oxacycles via Ruthenium-Catalyzed Atom-Economic Coupling of Propargyl Alcohols and Michael Acceptors

Synthesis of β-hydroxyenones and its application toward development of tetrahydro-4H-pyran-4-one in an atom-economic fashion is limited. This manuscript describes a ruthenium-catalyzed atom-economic coupling of pent-2-yne-1,5-diols and Michael acceptors as an efficient route for the synthesis of β-hydroxyenones with excellent yields and high regioselectivity. The β-hydroxyenones further undergo a 6-endo trig cyclization under acid-catalyzed conditions to deliver the tetrahydro-4H-pyran-4-ones with high diastereoselectivity. An intramolecular aldol condensation under mild basic conditions and palladium-catalyzed oxidative aromatization was developed for the synthesis of hexahydro-6H-isochromen-6-ones and isochromanols, respectively, from highly substituted tetrahydro-4H-pyran-4-ones with excellent yield and diastereoselectivity. Overall, this work demonstrates the synthetic potential toward the synthesis of oxacycles like tetrahydro-4H-pyran-4-ones, hexahydro-6H-isochromen-6-ones, and isochromanols via an atom-economic catalysis.

Construction of Silicon-Containing Seven-Membered Rings by Catalytic [4 + 2 + 1] Cycloaddition through Rhodium Silylenoid

A rhodium-catalyzed [4 + 2 + 1] cycloaddition involving 1,3-diene, alkyne, and silylene to afford silicon-containing seven-membered rings was established. In the presence of a rhodium catalyst bearing bis(diphenylphosphino)methane (DPPM), nona-1,3-dien-8-yne derivatives reacted efficiently at 80-110 °C with boryl(isopropoxy)silane or boryl(diethyamino)silane, which reacts as the synthetic equivalent of silylene, to afford 1-silacyclohepta-2,5-dienes (2,5-dihydro-1H-silepines). Regiodivergent and chemo- and stereoselective functionalization of the seven-membered nonconjugated diene was achieved by hydroboration mediated by Cs2CO3 or an iridium catalyst.

Chiral naphthyl-C2-indole as scaffold for phosphine organocatalysis: Application in asymmetric formal [4 + 2] cycloaddition reactions

The applications of a newly designed chiral naphthyl-C2-indole bifunctional phosphine organocatalyst in stereoselective formal [4 + 2] cycloaddition reactions were reported. The chiral naphthyl-C2-indole skeleton was introduced to bifunctional phosphine o

Manganese-Catalyzed Ring-Opening Coupling Reactions of Cyclopropanols with Enones

A manganese-catalyzed ring-opening coupling reaction of cyclopropanols with enones for the facile and efficient preparation of 1,6-diketones is described. A wide array of synthetically important 1,6-diketones bearing manifold functional groups are obtained with up to 93% yield. These reactions feature broad substrate scopes, environmentally benign conditions, inexpensive catalyst, and operational simplicity.

A Ba/Pd Catalytic System Enables Dehydrative Cross-Coupling and Excellent E-Selective Wittig Reactions

A Ba/Pd cooperative catalysis system was developed to enable the dehydrative cross-coupling of allylic alcohols with P-ylides to occur directly and promote a subsequent Wittig reaction in one pot. A variety of multisubstituted 1,4-dienes were isolated in good to excellent yields with broad P-ylides (stabilized by both ester and ketone carbonyl groups) and aldehyde (aliphatic and aromatic) substrates with excellent E selectivity.

Ruthenium-Catalyzed Redox Isomerizations inside Living Cells

Tailored ruthenium(IV) complexes can catalyze the isomerization of allylic alcohols into saturated carbonyl derivatives under physiologically relevant conditions, and even inside living mammalian cells. The reaction, which involves ruthenium-hydride intermediates, is bioorthogonal and biocompatible, and can be used for the "in cellulo" generation of fluorescent and bioactive probes. Overall, our research reveals a novel metal-based tool for cellular intervention, and comes to further demonstrate the compatibility of organometallic mechanisms with the complex environment of cells.

Enantio- A nd regioselective: Ene-reductions using F420H2-dependent enzymes

In the past decade it has become clear that many microbes harbor enzymes that employ an unusual flavin cofactor, the F420 deazaflavin cofactor. Herein we show that F420-dependent reductases (FDRs) can successfully perform enantio-, regio- A nd chemoselective ene-reductions. For the first time, we have demonstrated that F420H2-driven reductases can be used as biocatalysts for the reduction of α,β-unsaturated ketones and aldehydes with good conversions (>99%) and excellent regioselectivities and enantiomeric excesses (>99% ee). Noteworthily, FDRs typically display an opposite enantioselectivity when compared to the well established FMN-dependent Old Yellow Enzymes (OYEs).