1963-36-6

Usage

Uses

Used in Flavor and Fragrance Industry:
4-Methoxycinnamaldehyde is used as a flavoring agent for its cherry flesh, sweet taste, and cinnamic dry aromatic profile. It is particularly suitable for the creation of flavors in the food and beverage industry, enhancing the taste of various products.
4-Methoxycinnamaldehyde is also used as a fragrance ingredient in the perfumery industry, contributing to the spicy, floral scent of various perfumes and colognes.
Used in Chemical Research:
Due to its unique chemical properties, 4-Methoxycinnamaldehyde serves as a valuable compound in chemical research and development. It can be utilized in the synthesis of various organic compounds and may have potential applications in the pharmaceutical industry.

InChI:InChI=1/C10H10O2/c1-12-10-6-4-9(5-7-10)3-2-8-11/h2-8H,1H3/b3-2+

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 75-07-0 acetaldehyde 
• 53484-50-7 p-methoxycinnamyl alcohol 
• 135386-71-9 2-Phenyl-3-(4-methoxyphenyl)-5-hydroxyisoxazolidine 
• 37815-96-6 2-(4-methoxy-phenyl)-5-phenyl-3,6-dihydro-2H-pyran 
• 140-67-0 Estragole 
• 104-46-1 anethole 
• 7446-08-4 selenium(IV) oxide 
• 4180-23-8 E-1-(4'-methoxyphenyl)prop-1-ene 
• 603-35-0 triphenylphosphine 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 3054-95-3 acrylaldehyde diethyl acetal 
• 696-62-8 para-iodoanisole 
• 104-45-0 4-n-propylanisole 

Downstream Products

• 6342-88-7 (4-methoxy-cinnamylidene)-malonic acid 
• 50667-94-2 (2E,4E)-5-(4-methoxyphenyl)penta-2,4-dienoic acid 
• 62643-86-1 1-(4-chlorophenyl)-5-(4-methoxyphenyl)penta-2,4-dien-1-one 
• 55284-14-5 (E)-4-chloro-N-((E)-3-(4-methoxyphenyl)allylidene)aniline 
• 27394-81-6 5-(4'-methoxyphenyl)-2,4-pentadienal 
• 4842-77-7 5-(4-methoxy-phenyl)-1-phenyl-penta-2,4-dien-1-one 
• 62378-72-7 6-(4-methoxyphenyl)-3,5-hexadiene-2-one 
• 126772-76-7 7-(4-methoxy-phenyl)-1-phenyl-hepta-1,4,6-trien-3-one 
• 25163-70-6 1,5-bis(4-methoxyphenyl)penta-2,4-dien-1-one 
• 144561-03-5 5-(4-methoxy-phenyl)-1-(3-nitro-phenyl)-penta-2,4-dien-1-one 
• 66601-57-8 1,7-bis-(4-methoxy-phenyl)-hepta-1,4,6-trien-3-one 
• 122055-54-3 4-(4-methoxyphenyl)-1,1-dicyano-1,3-butadiene 
• 95161-74-3 1-<4-Methoxy-trans-cinnamyliden-(ξ)>-acenaphthenon-(2) ('p-Methoxycinnamyliden-acenaphthenon') vom F:202grad 
• 76553-92-9 4-[(E)-3-(4-Methoxy-phenyl)-prop-2-en-(E)-ylideneamino]-benzoic acid propyl ester 

Relevant academic research and scientific papers

Sodium bismuthate-induced oxidation of baccatin

Sodium bismuthate in acetic acid has proven very effective in the oxidation of allyic alcohols. An extension of this oxidation method using baccatin as the substrate has provided keto-baccatin, an important compound for the semisynthesis of Taxol and Taxotere. Copyright Taylor & Francis, Inc.

TWO PHENOLIC CONSTITUENTS FROM ALPINIA GALANGA RHIZOMES

Chemical investigation of the chloroform extract of the rhizomes of Alpinia galanga yielded p-hydroxycinnamaldehyde and methane.The former is isolated for the first time in nature and the latter is a new chemical component.These compounds were characterized from spectral studies and chemical reactions. - Key Word Index: Alpinia galanga; Zingiberaceae; p-hydroxycinnamaldehyde and methane.

Method for preparing olefine aldehyde by catalyzing terminal alkyne or terminal conjugated eneyne and diphosphine ligand used in method

The invention discloses a method for preparing olefine aldehyde by catalyzing terminal alkyne or terminal conjugated eneyne and a diphosphine ligand used in the method. According to the invention, indole-substituted phosphoramidite diphosphine ligand which is stable in air and insensitive to light is synthesized by utilizing a continuous one-pot method, and the indole-substituted phosphoramidite diphosphine ligand and a rhodium catalyst are used for jointly catalyzing to successfully achieve a hydroformylation reaction of aromatic terminal alkyne and terminal conjugated eneyne under the condition of synthesis gas for the first time, so that an olefine aldehyde structure compound can be rapidly and massively prepared, and particularly, a polyolefine aldehyde structure compound which is more difficult to synthesize in the prior art can be easily prepared and synthesized, and a novel method is provided for synthesis and modification of drug molecules, intermediates and chemical products.

A TEMPO-Functionalized Ordered Mesoporous Polymer as a Highly Active and Reusable Organocatalyst

The properties of high stability, periodic porosity, and tunable nature of ordered mesoporous polymers make these materials ideal catalytic nanoreactors. However, their application in organocatalysis has been rarely explored. We report herein for the first time the incorporation of a versatile organocatalyst, 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO), into the pores of an FDU-type mesoporous polymer via a pore surface engineering strategy. The resulting FDU-15-TEMPO possesses a highly ordered mesoporous organic framework and enhanced stability, and shows excellent catalytic activity in the selective oxidation of alcohols and aerobic oxidative synthesis of 2-substituted benzoxazoles, benzimidazoles and benzothiazoles. Moreover, the catalyst can be easily recovered and reused for up to 7 consecutive cycles.

Enantioselective Organocatalytic Synthesis of 1,2,3-Trisubstituted Cyclopentanes

An organocatalytic asymmetric domino Michael/α-alkylation reaction between enals and non-stabilized alkyl halides has been developed. Chiral secondary amine catalyzed cyclization reaction of 1-bromo-3-nitropropane with α,β-unsaturated aldehydes provides 1,2,3-trisubstituted cyclopentane carbaldehydes with high diastereo- (dr up to 8 : 1) and enantioselectivities (ee up to 96 %).

Method for preparing olefine aldehyde through catalytic oxidation of enol ether

The invention relates to the technical field of olefine aldehyde preparation, and provides a method for preparing olefine aldehyde through catalytic oxidation of enol ether. According to the invention, a palladium catalyst, a copper salt, a solvent and enol ether are mixed and subjected to a catalytic oxidation reaction to obtain olefine aldehyde. According to the method, the copper salt is used as the oxidizing agent, the mixed solvent of water and acetonitrile is used as the reaction solvent, and the volume ratio of water to acetonitrile in the mixed solvent is controlled to be (3-7): (3-7), so that the catalytic oxidation reaction can be smoothly carried out in the mixed solvent with a specific ratio, and the generation of palladium black precipitate can be avoided. The method provided by the invention has the advantages of simple steps, low reagent cost, no need of dangerous reagents, wide substrate adaptability and small catalyst dosage. Furthermore, octadecane mercaptan is added to promote the catalytic oxidation reaction, and when the dosage of the palladium catalyst is extremely low, the olefine aldehyde yield can be greatly increased by adding octadecane mercaptan.

Selective Rhodium-Catalyzed Hydroformylation of Terminal Arylalkynes and Conjugated Enynes to (Poly)enals Enabled by a π-Acceptor Biphosphoramidite Ligand

The hydroformylation of terminal arylalkynes and enynes offers a straightforward synthetic route to the valuable (poly)enals. However, the hydroformylation of terminal alkynes has remained a long-standing challenge. Herein, an efficient and selective Rh-catalyzed hydroformylation of terminal arylalkynes and conjugated enynes has been achieved by using a new stable biphosphoramidite ligand with strong π-acceptor capacity, which affords various important E-(poly)enals in good yields with excellent chemo- and regioselectivity at low temperatures and low syngas pressures.

One-Pot Preparation of (E)-α,β-Unsaturated Aldehydes by a Julia-Kocienski Reaction of 2,2-Dimethoxyethyl PT Sulfone Followed by Acid Hydrolysis

(E)-α,β-Unsaturated aldehydes were synthesized by the Julia-Kocienski reaction of 2,2-dimethoxyethyl 1-phenyl-1H-tetrazol-5-yl (PT) sulfone 3 with various aldehydes, followed by acid hydrolysis. The reaction could be carried out in one pot, and various (E)-α,β-unsaturated aldehydes were obtained in a short time and with high yields.

Saegusa Oxidation of Enol Ethers at Extremely Low Pd-Catalyst Loadings under Ligand-free and Aqueous Conditions: Insight into the Pd(II)/Cu(II)-Catalyst System

A highly efficient and practical Pd(II)/Cu(OAc)2-catalyst system of Saegusa oxidation, which converts enol ethers to the corresponding enals with a number of diverse substrates at extremely low catalyst loadings (500 mol ppm) under ligand-free and aqueous conditions, is described. Its synthetic utility was demonstrated by large-scale applications of the catalyst system to important nature molecules. This work allows Saegusa oxidation to become a highly practical approach to preparing enals and also suggests new insight into the Pd(II)/Cu(II)-catalyst system for dehydrogenation of carbonyl compounds and decreasing Pd-catalyst loadings.

Substrate-Controlled Chemo-/Enantioselective Synthesis of α-Benzylated Enals and Chiral Cyclopropane-Fused 2-Chromanone Derivatives

Substrate-controlled cascade reactions between α,β-unsaturated aldehydes or their analogues and 2,4-dinitrobenzyl chloride in the presence of a chiral secondary amine as the catalyst and base were developed, to obtain a broad spectrum of α-benzylated enals and enantioenriched cyclopropane-fused chroman-2-one derivatives. The cyclopropane-tethered iminium ion clearly served as a key intermediate in these reactions to trigger stereochemical outcomes, one of which was supported by a control experiment. (Figure presented.).