10225-38-4

Usage

Physical state

Yellow to amber liquid

Odor

Strong, sweet, and floral

Usage

Flavoring agent and fragrance ingredient in food and cosmetics industries; production of perfumes, soaps, and personal care products

Functionality

Enhances and modifies the aroma and flavor of various products; potential applications in medicinal and pharmaceutical formulations

Safety precautions

Skin and eye irritant; harmful if ingested or inhaled in large quantities

Upstream product

• 106-95-6 allyl bromide 
• 93-91-4 1-phenylbutan-1,3-dione 
• 107-05-1 3-chloroprop-1-ene 
• 107-18-6 allyl alcohol 
• 610-89-9 2-acetyl-pent-4-enoic acid ethyl ester 
• 4743-87-7 2-acetyl-pent-4-enoic acid 
• 35466-83-2 allyl methyl carbonate 
• 591-87-7 Allyl acetate 
• 109-49-9 5-Hexen-2-one 
• 93-89-0 benzoic acid ethyl ester 

Downstream Products

• 146896-37-9 (2-methyl-5-((phenylselanyl)methyl)-4,5-dihydrofuran-3-yl)(phenyl)methanone 
• 146896-35-7 3-acetyl-4,5-dihydro-2-phenyl-5-<(phenylseleno)methyl>furan 
• 1432739-11-1 2-(2-D-allyl)-1-phenylbutane-1,3-dione 
• 24836-01-9 (2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)(phenyl)methanone 
• 1432739-09-7 (1-(4-methoxyphenyl)-2,5-dimethyl-1H-pyrrol-3-yl)(phenyl)methanone 
• 1412887-48-9 C₁₃H₁₂O₂ 
• 1179891-13-4 4-allyl-1,3-dimethyl-5-phenyl-1H-pyrazole 
• 1179891-11-2 4-allyl-1-(4-methoxyphenyl)-3-methyl-5-phenyl-1H-pyrazole 
• 1179891-17-8 4-allyl-1-(4-methoxyphenyl)-5-methyl-3-phenyl-1H-pyrazole 
• 74971-29-2 endo-9-allyl-7,8-diaza-1,9-dimethyl-6-phenyltricyclo<4.2.1.0^2,5>nona-3,7-diene 

Relevant academic research and scientific papers

Copper(I) promoted C-C bond forming reactions: direct activation of allyl alcohols

Allylic alcohols, acetates, carbonates and chlorides can be activated by copper(I) salts towards nucleophilic substitution by carbon nucleophiles under relatively mild conditions.

Efficient allylation of nucleophiles catalyzed by a bifunctional heterogeneous palladium complex-tertiary amine system

We demonstrate the synergistic catalysis of a silica-supported diaminopalladium complex and a tertiary amine (SiO2/diamine/Pd/ NEt2) as well as synthetic scope of the Tsuji-Trost reaction of 1,3-dicarbonyls, phenols, and carboxylic acids with allyl carbonate and acetates. The synergistic catalysis of SiO2/diamine/Pd/NEt 2 exhibited wide applicability and high activity for the Tsuji-Trost reaction. For example, the reaction of ethyl 3-oxobutanate with allyl methyl carbonate afforded the allylated product in >99% yield at 70 °C for 5 h. The yield of allylated products was 26% for SiO2/diamine/Pd, without immobilization of the tertiary amine group. In the reaction of 1.0 mmol of ethyl 3-oxobutanate using 0.60 μmol of Pd in SiO2/diamine/Pd/NEt 2, the turnover number (TON) of Pd reached up to 1070 within 24 h. Phenols with electron-withdrawing groups, such as nitro and chloro groups, on the para position resulted in high product yields. The SiO2/diamine/ Pd/NEt2 catalyst was reusable at least 4 times without appreciable loss of its activity and selectivity in the reaction of p-chlorophenol. Copyright

Ionic liquid/water as a recyclable medium for Tsuji-Trost reaction assisted by microwave

An efficient microwave protocol is described for allylic substitution with various carbon and heteronucleophiles catalyzed by Pd(OAc)2/TPPTS in an [EMIm]BF4/H2O medium. The ionic liquid/water containing catalyst system can be recycled eight times without loss of activity.

Montmorillonite-entrapped sub-nanoordered Pd clusters as a heterogeneous catalyst for allylic substitution reactions

(Chemical Equation Presented) Caught making a change: Stable sub-nanoordered Pd clusters within the interlayer spaces of montmorillonite efficiently catalyze heterogeneous allylic substitution reactions in which the coordinatively unsaturated Pd atoms enable facile formation of π-allylpalladium intermediates (see scheme). The catalyst is reusable without any loss of activity or selectivity.

Synthesis of 3-Carbonyl Trisubstituted Furans via Pd-Catalyzed Aerobic Cycloisomerization Reaction: Development and Mechanistic Studies

Herein, we report the synthesis of 3-carbonyl-trisubstituted furans via Pd-catalyzed oxidative cycloisomerization reactions of 2-alkenyl-1,3-dicarbonyl scaffolds, using molecular oxygen as the sole oxidant to regenerate active palladium catalytic species, featuring good functional tolerance and mild reaction conditions. Deep investigation of intermediates and transition states of the reaction mechanism were conducted via experimental and DFT studies, providing a detailed mechanistical profile. The new developed methodology presents a greener alternative to Wacker-type cycloisomerizations and avoids the use of stoichiometric amounts of oxidants and strong acid additives.

Electrochemical oxidative cyclization of olefinic carbonyls with diselenides

The tandem cyclization of olefinic carbonyls with easily accessible diselenides facilitated by electrochemical oxidation has been successfully developed, which provides an environmentally friendly method for the construction of C-Se and C-O bonds simultaneously. A series of seleno dihydrofurans and seleno oxazolines, bearing fragile heterocycles, subtle C-I bonds and supernumerary vinyl groups, were forged using this elegant chelation strategy. Neither metal catalysts nor external chemical oxidants are required to promote this transformation.

Catalytic C?C Bond Formation Using a Simple Nickel Precatalyst System: Base- and Activator-Free Direct C-Allylation by Alcohols and Amines

A “totally catalytic” nickel(0)-mediated method for base-free direct alkylation of allyl alcohols and allyl amines is reported. The reaction is selective for monoallylation, uses an inexpensive NiII precatalyst system, and requires no activating reagents to be present.

Organic base-catalysed solvent-tuned chemoselective carbotrifluoromethylation and oxytrifluoromethylation of unactivated alkenes

An unprecedented and efficient organic base-catalysed highly chemoselective carbo- and oxytrifluoromethylation of unactivated alkenes with Togni's reagent was developed. The switchable chemoselectivity was tuned by simply changing the organic base catalyst and solvent. Mechanistic studies indicated that a radical cyclization pathway for carbotrifluoromethylation in DMSO and a carbocation pathway for oxytrifluoromethylation in DCE were probably involved.

Efficient synthesis of highly substituted pyrroles through a Pd(OCOCF 3)2-catalyzed cascade reaction of 2-alkenal-1,3-dicarbonyl compounds with primary amines

We describe an unprecedented Pd(OCOCF3)2-catalyzed cascade process for the synthesis of highly functionalized 1,2,3,5- tetrasubstituted pyrroles with high efficiency. Unlike documented methods relying on preformed enamines and active halogenated terminal alkenes, the process employs simple 2-alkenal-dicarbonyls and primary amines in 'one-pot'. The Royal Society of Chemistry 2013.

Palladium-Catalyzed Oxidative Alkoxylation of α-Alkenyl β-Diketones to Form Functionalized Furans

Treatment of 4-allyl-2,6-dimethyl-3,5-heptanedione with a catalytic amount of PdCl2(CH3CN)2 (5 mol %) and a stoichiometric amount of CuCl2 (2.2 equiv) in dioxane at 60 °C for 12 h formed 3-isobutyryl-2-isopropyl-5-methylfuran in 77% isolated yield. A number of α-alkenyl β-dike-tones underwent oxidative alkoxylation under these conditions to form 2,3,5-trisubsituted furans in moderate to good yield.