939-21-9

Usage

Uses

Used in Fragrance and Flavor Industry:
3-phenylpent-4-enal is used as a key ingredient in the production of fragrances and flavors due to its strong, sweet, and floral scent. It contributes significantly to the olfactory profile of various natural products such as jasmine, gardenia, and tea, enhancing their aroma and appeal.
Used in Pharmaceutical Research:
3-phenylpent-4-enal is being studied for its potential pharmacological properties, including its anti-inflammatory and antioxidant effects. This research aims to explore its therapeutic applications and benefits in the development of new medications and treatments.

InChI:InChI=1/C11H12O/c1-2-10(8-9-12)11-6-4-3-5-7-11/h2-7,9-10H,1,8H2

Upstream product

• 940-52-3 3-phenyl-2-propenyl vinyl ether 
• 80816-24-6 (E)-[3-(vinyloxy)prop-1-en-1-yl]benzene 
• 82263-47-6 (2S,3R,4S,5R)-3,4-Dimethyl-5-phenyl-2-((E)-styryl)-oxazolidine 
• 75927-49-0 pinacol vinylboronate 
• 111-34-2 -butyl vinyl ether 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 60066-61-7 ethyl 3-phenyl-4-pentenoate 
• 88083-18-5 (E)-3-<(E)-3-phenyl-2-propenoxy>propenoic acid 
• 80816-30-4 3-phenyl-4-pentenol 
• 130655-07-1 1-Chloro-4-[2-((E)-3-phenyl-allyloxy)-ethanesulfinyl]-benzene 
• 130655-01-5 C₁₇H₁₈O₂S 
• 80816-23-5 (E)-3-phenyl-3-vinyloxyprop-1-ene 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 75-07-0 acetaldehyde 

Downstream Products

• 127826-96-4 N-(3-phenyl-4-pentylidene)-2-benzothiazolesulfenamide 
• 127826-97-5 N-(3-phenyl-4-pentylidene)-2-benzenesulfenamide 
• 5703-57-1 3-phenylpent-4-enoic acid 
• 34097-95-5 3-Phenylpentanal 
• 80816-30-4 3-phenyl-4-pentenol 
• 64145-51-3 3-phenylcyclopentanone 
• 95921-51-0 5-(1-hexenyl)-2-methyl-3-phenyl-2-oxolene 
• 95921-50-9 3-phenyl-1,6-undecadien-5-ol 
• 95921-26-9 2-iodomethyl-5-(1-hexenyl)-3-phenyloxolane 
• 53646-85-8 1,3-diphenyl-1H-pyrrole 
• 66515-33-1 2-phenylsuccinaldehyde 
• 2845-27-4 3-phenylpentanoic acid 
• 173673-32-0 3,4-dihydro-2-methyl-3-phenyl-2H-pyrrole 
• 182194-87-2 1-tosyloxy-3-phenylpent-4-ene 

Relevant academic research and scientific papers

Acceleration of a dipolar Claisen rearrangement by hydrogen bonding to a soluble diaryl urea

The Claisen rearrangement of 6-methoxy allyl vinyl ether is catalyzed by a soluble diaryl urea, and evidence is presented that the urea stabilizes a dipolar transition state by hydrogen bonding.

Regioselective allylzincation of alkenylboronate

(Formula Presented) Boryl substitution on an olefin activates the olefinic double bond toward addition of an organozinc reagent. Addition of an allylic zinc reagent to an alkenylboronate thus takes place smoothly to afford a variety of gem-zincio/boryl species. Theoretical studies with density functional calculations on the reaction pathway revealed that the reaction proceeds via a zincio-ene reaction rather than a bora-Claisen rearrangement.

Enantioselective Iridium-Catalyzed α-Allylation with Aqueous Solutions of Acetaldehyde

The enantioselective α-allylation of aqueous solutions of acetaldehyde using iridium- A nd amine-catalyzed substitution of racemic allylic alcohols is described. The method utilizes a readily available, safely handled aqueous solution of acetaldehyde and furnishes ?,?-unsaturated aldehydes in good yields and greater than 99% enantiomeric excess. The synthetic potential of the method is demonstrated with the enantioselective formal syntheses of heliannuols C and E as well as heliespirones A and C.

Synthesis of 1,3- and 1,2,3-functionalized pyrroles via Ir(I)-catalyzed vinylation of allyl alcohols

[Figure not available: see fulltext.] An efficient method for the preparation of 1,3-disubstituted and 1,2,3-trisubstituted pyrroles was developed through a sequence involving O-vinylation of allyl alcohols followed by Claisen rearrangement and further ozonolysis, concurring in a Paal–Knorr reaction with primary amines. Hg(II) and Ir(I) catalysts and different vinylating reagents were tested. The best results were consistently obtained with the [Ir(cod)Cl]2–vinyl acetate system. The featured methodology gives access to functionalized pyrroles in overall good yields, whose chemical architecture may awake interest for assorted applications.

Enantioselective Claisen rearrangements with a hydrogen-bond donor catalyst

N,N-Diphenylguanidinium ion associated with the noncoordinating BArF counterion is shown to be an effective catalyst for the [3,3]-sigmatropic rearrangement of a variety of substituted allyl vinyl ethers. Highly enantioselective catalytic Claisen rearrangements of ester-substituted allyl vinyl ethers are then documented using a new C2-symmetric guanidinium ion derivative. Copyright

Highly regioselective [3,3] rearrangement of aliphatic allyl vinyl ethers catalyzed by a metalloporphyrin complex, Cr(TPP)Cl

The Claisen rearrangement of simple aliphatic allyl vinyl ethers catalyzed by a metalloporphyrin, Cr(TPP)Cl, is described. The porphyrin-based Lewis acid catalyst can effectively accelerate the rearrangement via a concerted [3,3] pathway with a minimal degree of bond ionization of the substrates, providing the corresponding Claisen products in moderate to high yields and almost perfect regioselectivity at low catalyst loading.

One-pot Claisen rearrangement with n-butyl vinyl ether

A protocol for one-pot Claisen rearrangement with n-butyl vinyl ether is described. Upon heating allylic alcohols with excess n-butyl vinyl ether with catalytic amount of Hg(OAc)2 and NaOAc, Claisen rearrangement takes place through in situ formation of the requisite allyl vinyl ether.

Iminyl Radicals: Part I. Generation and Intramolecular Capture by an Olefin.

Slow addition of tributylstannane to sulphenylimines 2 give the corresponding Δ1-pyrrolenines 5 by an intramolecular addition of the intermediate iminyl radical, a process which can be easily coupled to an intermolecular addition to an electrophilic olefin.

Preparation and rearrangement of 2-allyloxyethyl aryl sulfoxides; a mercury-free claisen sequence

Alkali metal hydride promoted addition of allylic alcohols to aryl vinyl sulfoxides at room temperature gives 2-allyloxyethyl aryl sulfoxides, which, on heating, are converted into γ,δ-unsaturated aldehydes via allylic vinyl ethers.

Organoaluiminum-promoted claisen rearrangement of allyl vinyl ethers

Unprecedentad stereochemical control has achieved in the Claisen of allyl vinyl of type 4 with certain bulky organoaluminum Thus, methylaluminum bis(4-bromo-2,6-di-tert-butylphenoxide) (reagent A) can be utilized for obtaining the (Z) isomer, (Z)-6, whereas the (E) isomer, (E)-6 was produced with methylaluminum bis(2,6-diphenylphenoxide) (reagent B). This organoaluminum-promoted Claisen rearrangement proceeds under very mild conditions with very good E and Z selectlvities. On the basis of the Claisen rearrangement of optically active substrate 7 with reagent A, the Z selectivity would be interpreted by the intervention of the chairlike transition-state conformation with the isobutyl substituent axial. The present organoalunminum-promoted Claisen rearrangement has successfully applied to the synthesis of (4E,7Z)-4,7-tridecadienyl acetate (15), a component of the sex of tuberworm moth, in stereoselective fashion. Furthermore, the Claisen rearrangement of bisallyl vinyi ether16 with reagent A or B has been found to involve the more substituted allylic system to furnish dienal 18 preferentially, not obtainable in the ordinary thermal rearrangement. This chemistry been further extended to the ionic rearrangement of dienyl vinyl ether 28 by using reagent A in a polar solvent the previously unknown, remote transfer of the vinyloxy moiety by [3,5]-sigmatropic rearrangement via ionic intermediate 29 has observed.