65401-83-4

Usage

Uses

Used in Pharmaceutical Industry:
4-(2-formylvinyl)-2-methoxyphenyl acetate is used as an intermediate in the synthesis of pharmaceutical compounds for its versatile chemical properties, allowing for the development of new drugs with potential therapeutic benefits.
Used in Flavor and Fragrance Industry:
4-(2-formylvinyl)-2-methoxyphenyl acetate is utilized as a key ingredient in the creation of unique fragrances and flavors due to its distinct aromatic profile, enhancing the sensory experience of various consumer products.
Used in Chemical Research:
4-(2-formylvinyl)-2-methoxyphenyl acetate serves as a valuable research tool in organic chemistry, enabling scientists to explore new reactions and mechanisms, ultimately contributing to the advancement of chemical knowledge.
Used in Material Science:
In the field of material science, 4-(2-formylvinyl)-2-methoxyphenyl acetate is employed in the development of novel materials with specific properties, such as improved stability or reactivity, for various applications including coatings, adhesives, and polymers.

InChI:InChI=1/C12H12O4/c1-9(14)16-11-6-5-10(4-3-7-13)8-12(11)15-2/h3-8H,1-2H3/b4-3+

Upstream product

• 93-28-7 eugenol acetate 
• 97-53-0 4-allylguaiacol 
• 458-36-6 trans-coniferyl aldehyde 
• 108-24-7 acetic anhydride 
• 881-68-5 vanillin acetate 
• 52509-14-5 (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide 
• 1006614-61-4 2-methoxy-4-(3-oxopropyl)phenyl ethanoate 
• 69017-41-0 (E)-3-(4-acetoxy-3-methoxyphenyl)-2-propen-1-ol 
• 2596-47-6 (E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 5912-87-8 (E)-1-(4-acetoxy-3-methoxyphenyl)-1-propene 
• 50906-12-2 4-acetoxy-3-methoxycinnamoyl chloride 
• 20649-42-7 coniferaldehyde 
• 84-58-2 2,3-dicyano-5,6-dichloro-p-benzoquinone 

Downstream Products

• 1186656-09-6 4-[(1S,3aS,6R,6aR)-3a,6-dihydroxyhexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenyl acetate 
• 1352411-37-0 3-(4-acetoxy-3-methoxyphenyl)-5-oxo-2-(pyridine-2-sulfonyl)-pentanoic acid methyl ester 
• 1352411-60-9 C₂₂H₂₇NO₉S 
• 1422364-13-3 C₁₈H₁₆O₄ 
• 1422364-14-4 C₁₉H₁₈O₅ 
• 1422364-16-6 C₁₈H₁₆O₅ 
• 81766-26-9 4-O-acetyl-coniferyl alcohol 
• 1006614-61-4 2-methoxy-4-(3-oxopropyl)phenyl ethanoate 

Relevant academic research and scientific papers

Synthesis method of 4-hydroxycinnamaldehyde compound

The invention relates to the field of organic synthesis and agricultural chemistry, and particularly discloses a synthesis method of a 4-hydroxycinnamaldehyde compound shown as a formula II. The synthesis method comprises the following steps: with 4-hydroxy-allylbenzene as a raw material, firstly performing hydroxyl protection, then with 2, 3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as an oxidant and water (H2O) as a nucleophile, oxidizing an allyl group into alpha, beta-unsaturated aldehyde (namely, a cinnamaldehyde structure) under a relatively mild condition, and finally performing deprotection to obtain a target product. The invention elaborates a novel synthesis method of the 4-hydroxycinnamaldehyde compound. The novel synthesis method has the characteristics of no transition metalparticipation, a simple and mild reaction condition, high product yield and the like, and has a wide application prospect in the field of the agricultural chemistry, especially in plant science and bioenergy conversion.

DDQ-mediated oxidation of allylarenes: Expedient access to cinnamaldehyde-containing phenylpropanoids

Phenylpropanoid natural products containing a cinnamaldehyde motif were easily synthesized from allylarenes mediated by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidation. Representative examples described herein are five types of 4-hydroxycinnamaldehyde derivatives from monolignols biosynthesis, Boropinal C, and 7-methoxywutaifuranal from plant extracts. Especially, simple synthesis of 7-methoxywutaifuranal was exploited through selective mono-oxidation and subsequent isomerization-ring-closing-metathesis strategy.

A selective and mild glycosylation method of natural phenolic alcohols

Several bioactive natural p-hydroxyphenylalkyl β-D-glucopyranosides, such as vanillyl β-D-glucopyranoside, salidroside and isoconiferin, and their glycosyl analogues were prepared by a simple reaction sequence. The highly efficient synthetic approach was achieved by utilizing acetylated glycosyl bromides as well as aromatic moieties and mild glycosylation promoters. The aglycones, p-O-acetylated arylalkyl alcohols, were prepared by the reduction of the corresponding acetylated aldehydes or acids. Various stereoselective 1,2-trans-O-glycosylation methods were studied, including the DDQ-iodine or ZnO-ZnCl2 catalyst combination. Among them, ZnO-iodine has been identified as a new glycosylation promoter and successfully applied to the stereoselective glycoside synthesis. The final products were obtained by conventional Zemplén deacetylation.

p-Coumaroyl-CoA:Monolignol Transferase

The invention relates to nucleic acids encoding a p-coumaroyl-CoA:monolignol transferase and to inhibitory nucleic acids adapted to inhibit the expression and/or translation of a p-coumaroyl-CoA:monolignol transferase RNA. Inhibition of p-coumaroyl-CoA:monolignol transferase in plants improves the incorporation of monolignol ferulates into the lignin of plants, giving rise to plant biomass that is more easily processed into useful products such as paper and biofuels.

FERULOYL-CoA:MONOLIGNOL TRANSFERASE

The invention relates to nucleic acids encoding a feruloyl-CoA:monolignol transferase and the feruloyl-CoA:monolignol transferase enzyme that enables incorporation of monolignol ferulates, for example, including p-coumaryl ferulate, coniferyl ferulate, and sinapyl ferulate, into the lignin of plants.

Efficient preparation of trans-α,β-unsaturated aldehydes from saturated aldehydes by oxidative enamine catalysis

A mild and highly efficient amine-catalyzed, IBX-mediated oxidation of aldehydes to (E) selective α,β-unsaturated aldehydes has been achieved in good yields. The process features a new oxidation of enamines to iminium ions in a catalytic fashion.

Synthesis of cinnamaldehydes by oxidation of arylpropenes with 2,3-dichloro-5,6-dicyanoquinone

Alkoxylated 1-aryl-1-propenes [1-(4-methoxyphenyl)-1-propene, 1-(3,4-dimethoxyphenyl)-1-propene, 1-(3,4,5-trimethoxyphenyl)-1-propene] and 3-aryl-1-propenes [3-(4-methoxyphenyl)-1-propene, 3-(3,4-dimethoxyphenyl)-1-propene 3-(3,4,5-trimethoxyphenyl)-1-propene] gave cinnamaldehydes in 71-84% yield on treatment with 2,3-dichloro-5,6-dicyanoquinone (DDQ) (slight excess) at room temperature for 0.5-2 h in the two-phase system dichloromethane-water (4:1). Arylpropenes lacking electron-donating alkoxy groups (1-phenyl-1-propene, 3-phenyl-1-propene) or carrying an acetoxy group [1-(4-acetoxy-3-methoxyphenyl)-1-propene, 3-(4-acetoxy-3-methoxyphenyl)-1-propene] were converted into cinnamaldehydes in low to moderate yields on oxidation with a large excess of DDQ in combination with long reaction times (> 12 h). All the 1-aryl-1-propones examined were rapidly converted into a mixture of mono-and bis-(3-aryl-2-propenyl) ethers of 2,3-dichloro-5,6-dicyanohydroquinone (DDHQ) on DDQ oxidation. The rate of formation of DDHQ ethers from alkoxy-substituted 3-aryl-1-propenes was slightly lower. 3-Phenyl-1-propene and also 3-(4-acetoxy-3-methoxyphenyl)-1-propene were largely unchanged at the initial stage of the oxidation. Significant differences in the compositions of the DDHQ ether mixtures obtained from 1-aryl-1-propenes and 3-aryl-1-propones were not observed. Acta Chemica Scandinavica 1998.

Facile Synthesis of 4-Hydroxycinnamyl p-Coumarates

Coniferyl p-coumarate (4-hydroxy-3-methoxycinnamyl 4-hydroxycinnamate) and sinapyl p-coumarate (3,5-dimethoxy-4-hydroxycinnamyl 4-hydroxycinnamate) were synthesized in high overall yield. In this improved method acetate was used as the phenol protecting group instead of 2,4-dinitrophenyl ether; selective deacetylation, without cinnamate ester hydrolysis, was accomplished with neat pyrrolidine.

Synthesis of cinnamaldehydes, esters of cinnamic acids and acylals of cinnamaldehydes by oxidation of arylpropenes with 2,3-dicyano-5,6- dichlorobenzoquinone (DDQ)

1-Arylpropenes and 3-arylpropenes give cinnamaldehydes (yield= 80%) on oxidation with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) in the presence of water. The conversion to aldehydes is promoted by electron-donating groups at the aromatic ring. On DDQ oxidation in the presence of methanol, methyl esters of cinnamic acids are the predominant products. DDQ oxidation of 1- or 3-(3,4-dimethoxyphenyl)-1-propene in the presence of acetic acid gives an acylal [the diacetate of (E)-3-(3,4-dimethoxyphenyl)-2-propene-1, 1-diol].

Phase transfer Wittig reaction with 1,3-dioxolan-2-yl-methyltriphenyl phosphonium salts: An efficient method for vinylogation of aromatic aldehydes

Aldehydes were efficiently transformed into allylic dioxolanes by a Wittig-type reaction, using 1,3-dioxolan-2-yl-methyltriphenylphosphonium bromide under phase transfer conditions. The substituent kinetic effects were studied, and related to Hammett values and electrochemical potentials.