5919-69-7

Usage

Uses

Used in the Food and Beverage Industry:
[(1Z)-3-ethoxyprop-1-en-1-yl]benzene is used as a flavoring agent for enhancing the taste and aroma of various food and beverage products. Its strong, sweet odor makes it a suitable candidate for creating appealing flavors in the culinary world.
Used in the Cosmetic and Personal Care Products Industry:
In the cosmetic and personal care sector, [(1Z)-3-ethoxyprop-1-en-1-yl]benzene serves as a fragrance component, adding a pleasant scent to products such as perfumes, lotions, and shampoos. Its sweet odor contributes to the overall sensory experience of these products.
Used in the Chemical Synthesis Industry:
[(1Z)-3-ethoxyprop-1-en-1-yl]benzene can also be utilized as an intermediate in the synthesis of other organic compounds. Its chemical structure allows for further reactions and modifications, making it a valuable building block in the creation of more complex molecules.
Safety Precautions:
It is important to handle [(1Z)-3-ethoxyprop-1-en-1-yl]benzene with care, as it has the potential to cause irritation to the skin, eyes, and respiratory system if not used properly. Appropriate safety measures should be taken to minimize the risk of exposure and ensure the well-being of those who work with [(1Z)-3-ethoxyprop-1-en-1-yl]benzene.

Upstream product

• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 4392-24-9 Cinnamyl bromide 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 64-67-5 diethyl sulfate 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 64-17-5 ethanol 
• 5044-52-0 vinyltriphenylphosphonium bromide 
• 100-52-7 benzaldehyde 
• 300-57-2 allylbenzene 
• 23250-03-5 β-hydroxyethyltriphenylphosphonium chloride 
• 7647-01-0 hydrogenchloride 
• 21040-45-9 Cinnamyl acetate 
• 201230-82-2 carbon monoxide 
• 106625-69-8 ethyl (E)-3-phenyl-2-propenyl carbonate 

Downstream Products

• 22554-02-5 ethyl N-(3-phenylprop-2-enyl)carbamate 
• 95964-32-2 ethyl N-(1-phenylallyl)carbamate 
• 55666-17-6 (1E)-1,4-pentadienylbenzene 
• 36004-04-3 ethyl (E)-1-phenylbut-1-en-3-ol 
• 14371-10-9 (E)-3-phenylpropenal 
• 58506-33-5 5-phenyl-trans,trans-2,4-pentadien-1-ol 
• 38447-05-1 (2E,4E)-methyl 5-phenylpenta-2,4-dienoate 
• 24808-74-0 (E)-(3-methoxybut-1-en-1-yl)benzene 
• 112655-08-0 ((1E,3E)-5-methoxypenta-1,3-dien-1-yl)benzene 
• 1896-62-4 (E)-benzalacetone 
• 13466-40-5 (2E, 4E)-5-phenylpenta-2,4-dienal 
• 123-01-3 1-dodecylbenzene 
• 100-52-7 benzaldehyde 
• 65-85-0 benzoic acid 

Relevant academic research and scientific papers

Oxoammonium-Mediated Allylsilane–Ether Coupling Reaction

A new C(sp3)?H functionalization reaction consisting of the oxidative α-allylation of allyl- and benzyl- methyl ethers has been developed. The C?C coupling could be carried out under mild conditions thanks to the use of cheap and green oxoammonium salts. The scope of the reaction was studied over 27 examples, considering the nature of the substituents on the two coupling partners.

Bioactivity and structure–activity relationship of cinnamic acid derivatives and its heteroaromatic ring analogues as potential high-efficient acaricides against Psoroptes cuniculi

A series of cinnamic acid derivatives and its heteroaromatic ring analogues were synthesized and evaluated for acaricidal activity in vitro against Psoroptes cuniculi, a mange mite. Among them, eight compounds showed the higher activity with median lethal concentrations (LC50) of 0.36–1.07 mM (60.4–192.1 μg/mL) and great potential for the development of novel acaricidal agent. Compound 40 showed both the lowest LC50 value of 0.36 mM (60.4 μg/mL) and the smallest median lethal time (LT50) of 2.6 h at 4.5 mM, comparable with ivermectin [LC50 = 0.28 mM (247.4 μg/mL), LT50 = 8.9 h], an acaricidal drug standard. SAR analysis showed that the carbonyl group is crucial for the activity. The type and chain length of the alkoxy in the ester moiety and the steric hindrance near the ester group significantly influence the activity. The esters were more active than the corresponding thiol esters, amides, ketones or acids. Replacement of the phenyl group of cinnamic esters with α-pyridyl or α-furanyl significantly increase the activity. Thus, a series of cinnamic esters and its heteroaromatic ring analogues with excellent acaricidal activity emerged.

Auto-Tandem Catalysis with Frustrated Lewis Pairs for Reductive Etherification of Aldehydes and Ketones

Herein we report that a single frustrated Lewis pair (FLP) catalyst can promote the reductive etherification of aldehydes and ketones. The reaction does not require an exogenous acid catalyst, but the combined action of FLP on H2, R-OH or H2O generates the required Br?nsted acid in a reversible, “turn on” manner. The method is not only a complementary metal-free reductive etherification, but also a niche procedure for ethers that would be either synthetically inconvenient or even intractable to access by alternative synthetic protocols.

MnO2/TBHP: A Versatile and User-Friendly Combination of Reagents for the Oxidation of Allylic and Benzylic Methylene Functional Groups

In the presence of activated MnO2, tert-butyl hydroperoxide (TBHP) in CH2Cl2 is able to oxidize the allylic and benzylic methylene groups of different classes of compounds. I describe a one-pot oxidation protocol based on two sequential steps. In the first step, carried out at low temperature, MnO2 catalyses the oxidation of the methylene group. This is followed by a second step where reaction temperature is increased, allowing MnO2 both to catalyse the decomposition of unreacted TBHP and to oxidize allylic alcohols that could possibly be formed. The proposed oxidation procedure is generally applicable, although its efficiency, regioselectivity, and chemoselectivity are strongly dependent on the structure of the substrate. A simple and user-friendly synthetic procedure for the oxidation of allylic and benzylic methylene groups to the corresponding conjugated carbonyl derivatives is described. The proposed oxidation protocol is based on the combined use of MnO2 and tert-butyl hydroperoxide, and is generally applicable.

Oxidative cleavage of allyl ethers by an oxoammonium salt

A method to oxidatively cleave allyl ethers to their corresponding aldehydes mediated by an oxoammonium salt is described. Using a biphasic solvent system and mild heating, cleavage proceeds readily, furnishing a variety of α,β-unsaturated aldehydes and ketones.

Homogeneous Pd-catalyzed transformation of terminal alkenes into primary allylic alcohols and derivatives

Synthesis of primary alcohols from terminal alkenes is an important process in both bulk and fine chemical syntheses. Herein, a homogeneous Pd-complex-catalyzed transformation of terminal alkenes into primary allylic alcohols, by using 5 mol % [Pd(PPh3)4] as a catalyst, and H2O, CO2, and quinone derivatives as reagents, is reported. When alcohols were used instead of H2O, allylic ethers were obtained. A proposed mechanism includes the addition of oxygen nucleophiles at the less-hindered terminal position of π-allyl Pd intermediates.

Step-economy etherification of acylated alcohols

An efficient and convenient protocol has been developed for ether bond formation in mild conditions. A mixture of primary/secondary ester and allylic/benzylic halide in tetrahydrofuran was treated with KOtBu at room temperature to give ether in high yield. This step economic method enabled direct alkylation of the acyl group masked O-nucleophiles. Application of this method in carbohydrate synthesis was feasible and chemo-selectivity can be achieved.

Hydrogen-bond-activated palladium-catalyzed allylic alkylation via allylic alkyl ethers: Challenging leaving groups

C-O bond cleavage of allylic alkyl ether was realized in a Pd-catalyzed hydrogen-bond-activated allylic alkylation using only alcohol solvents. This procedure does not require any additives and proceeds with high regioselectivity. The applicability of this transformation to a variety of functionalized allylic ether substrates was also investigated. Furthermore, this methodology can be easily extended to the asymmetric synthesis of enantiopure products (99% ee).

Multimetallic Ir-Sn3-catalyzed substitution reaction of π-activated alcohols with carbon and heteroatom nucleophiles

An atom economic and catalytic substitution reaction of π-activated alcohols by a multimetallic IreSn3 complex has been demonstrated. The multimetallic IreSn3 complex can be easily synthesized from the reaction between [Cp*IrCl2]2 and SnCl2. In presence of as little as 1 mol % of the catalyst three different types of π-activated alcohols, namely benzyl, allyl, and propargyl alcohols, have been successfully transformed into alkylated products using carbon (arenes, heteroarenes, allyltrimethylsilane, and 1,3-dicarbonyls), nitrogen (sulfonamides), oxygen (alcohols), and sulfur (thiols) nucleophiles in very high yields. An electrophilic mechanism is proposed from the Hammett correlation study.

Nickel-catalyzed allylic substitution of simple alkenes

This report describes a nickel-catalyzed allylic substitution process of simple alkenes whereby an important structural motif, a 1,4-diene, was prepared. The key to success is the use of an appropriate nickel-phosphine complex and a stoichiometric amount of silyl triflate. Reactions of 1-alkyl-substituted alkenes consistently provided 1,1-disubstituted alkenes with high selectivity. Insight into the reaction mechanism as well as miscellaneous application of the developed catalytic process is also documented.