1794-45-2

Usage

Uses

Used in Flavor and Fragrance Industry:
2-Chlorocinnamaldehyde is used as a flavoring agent and fragrance ingredient in the food and cosmetic industries, leveraging its distinctive sweet and floral scent to enhance the sensory experience of products.
Used in Pharmaceutical Production:
In the pharmaceutical sector, 2-Chlorocinnamaldehyde serves as a crucial component in the manufacturing process, contributing to the development of various medicinal compounds.
Used as an Intermediate in Organic Synthesis:
2-Chlorocinnamaldehyde is utilized as an intermediate in organic synthesis, playing a key role in the creation of a range of chemical products through chemical reactions.
Used in Antimicrobial and Antitumor Research:
2-Chlorocinnamaldehyde has been studied for its potential antimicrobial and antitumor properties, indicating its possible use in the development of treatments for infections and cancer.
It is important to handle 2-Chlorocinnamaldehyde with care due to its potential to cause irritation to the skin, eyes, and respiratory system.

InChI:InChI=1/C9H7ClO/c10-9-6-2-1-4-8(9)5-3-7-11/h1-7H/b5-3+

Upstream product

• 89-98-5 2-chloro-benzaldehyde 
• 75-07-0 acetaldehyde 
• 56-23-5 tetrachloromethane 
• 120681-06-3 3-(2-chlorophenyl)propenoyl chloride 
• 3752-25-8 o-chlorocinnamic acid 
• 75-27-4 bromodichloromethane 
• 2039-87-4 2-chlorostyrene 
• 782498-45-7 C₉H₉ClO₂ 
• 14371-10-9 (E)-3-phenylpropenal 
• 148775-24-0 (2E)-3-(2-chlorophenyl)-prop-2-en-1-ol 
• 108-05-4 vinyl acetate 
• 704-96-1 trans-2-chlorocinnamic acid 
• 157433-36-8 3-(2-chlorophenyl)propanal 
• 298-12-4 Glyoxilic acid 

Downstream Products

• 1062117-96-7 (4R)-4-(2-chlorophenyl)-2-hydroxy-3,4,7,8-tetrahydro-2H-chromen-5(6H)-one 
• 1062118-18-6 (4R)-4-(2-chlorophenyl)-2-hydroxy-7,7-dimethyl-3,4,7,8-tetrahydro-2H-chromen-5(6H)-one 
• 1134193-25-1 1-(o-chlorophenyl)-2-(o-chlorophenyl)-5-benzoyl-1,2-dihydropyridine 
• 1134193-16-0 4-(o-chlorophenyl)-1-(p-fluorophenyl)-3-benzoyl-1,4-dihydropyridine 
• 1134193-17-1 4-(o-chlorophenyl)-1-(p-bromophenyl)-3-(p-chlorobenzoyl)-1,4-dihydropyridine 
• 1146770-48-0 (4R)-4-(2-chlorophenyl)-2-hydroxy-7-methyl-3,4-dihydropyrano-[4,3-b]-pyran-5(2H)-one 
• 1159012-12-0 3-(2-chlorobenzyl)-5-methoxy-7-methyl-2H-chromen-2-one 
• 1151841-85-8 (R)-3-(2-chlorophenyl)-3-(4,7-dihydro-1H-indol-2-yl)propanal 
• 1181810-10-5 (4R)-4-(2-chlorophenyl)-3,4-dihydro-2H-benzo[h]chromen-2-ol 
• 1208396-43-3 (S)-3-(2-chlorophenyl)-3H-pyrrolo[1,2-a]indole-2-carbaldehyde 
• 112853-60-8 3-(2-chlorophenyl)-5-hydroxy-2-isoxaline 

Relevant academic research and scientific papers

Preparation method of alpha-deuterated olefine aldehyde

The invention relates to a preparation method of alpha-deuterated olefine aldehyde, which comprises the following steps: by taking alpha, beta-olefine aldehyde as a raw material, carrying out a reversible Michael addition mechanism under the action of deuterium water, a nucleophilic reagent and an organic catalyst to obtain an alpha-deuterated olefine aldehyde compound. The method has high selectivity, and does not generate deuterated by-products at other positions. The alpha-deuterated olefine aldehyde compound prepared by the invention has great application value, can be further widely converted to prepare mono (poly) deuterated olefin and derivatives, olefine acid, conjugated olefine aldehyde, eneyne and other compounds, and has important significance in drug synthesis.

Enantiodivergent One-Pot Synthesis of Axially Chiral Biaryls Using Organocatalyst-Mediated Enantioselective Domino Reaction and Central-to-Axial Chirality Conversion

Enantiodivergent one-pot synthesis of biaryls was developed using a catalytic amount of a single chiral source. A domino organocatalyst-mediated enantioselective Michael reaction and aldol condensation provided centrally chiral dihydronaphthalenes with excellent enantioselectivity, from which an enantiodivergent chirality conversion from central-to-axial chirality was achieved. Both enantiomers of biaryls were obtained with excellent enantioselectivity. All transformations can be conducted in a single reaction vessel. A plausible reaction mechanism for the enantiodivergence is proposed.

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.

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.

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 %).

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.).

Potent Inhibition of Nicotinamide N-Methyltransferase by Alkene-Linked Bisubstrate Mimics Bearing Electron Deficient Aromatics

Nicotinamide N-methyltransferase (NNMT) methylates nicotinamide (vitamin B3) to generate 1-methylnicotinamide (MNA). NNMT overexpression has been linked to a variety of diseases, most prominently human cancers, indicating its potential as a therapeutic target. The development of small-molecule NNMT inhibitors has gained interest in recent years, with the most potent inhibitors sharing structural features based on elements of the nicotinamide substrate and the S-adenosyl-l-methionine (SAM) cofactor. We here report the development of new bisubstrate inhibitors that include electron-deficient aromatic groups to mimic the nicotinamide moiety. In addition, a trans-alkene linker was found to be optimal for connecting the substrate and cofactor mimics in these inhibitors. The most potent NNMT inhibitor identified exhibits an IC50 value of 3.7 nM, placing it among the most active NNMT inhibitors reported to date. Complementary analytical techniques, modeling studies, and cell-based assays provide insights into the binding mode, affinity, and selectivity of these inhibitors.

Boosting multiple photo-assisted and temperature controlled reactions with a single redox-switchable catalyst: Solvents as internal substrates and reducing agent

An alternative and economically viable process for the synthesis of β-aryl enals, enones and the aryl amines has been developed by partial oxidation of ethanol, isopropanol and N, N-dimethyl formamide (DMF). The formation of β-aryl enals, enones and the aryl amines was catalyzed by a mixed metal oxides layer of cobalt and chromium supported on halloysite nanotubes, designated as CoCr2O4-HNT. The C[sbnd]C and C[sbnd]N bond formation reactions were found to be influenced by temperature and the nature of base. The condensation of aldehyde with in situ generated acetaldehyde by ethanol oxidation forming β-aryl enals occurred selectively at 120 °C. The partial oxidation of isopropanol to acetone and its condensation with aldehydes forming β-aryl enones occurred at room temperature. Increase in temperature caused the liberation of hydrogen gas from isopropanol and allowed the reversible reduction of aldehydes to alcohols. Increase in temperature in isopropanol and increase in base concentration in ethanol causes the selective reduction of aldehydes to alcohols. Besides being active for the Claisen-Schmidt type of reactions and the aryl halides amination process, the synthesized catalyst was also found to be highly active for the photocatalytic oxidation of benzyl alcohols in absence of any external oxidizing agent. The positive holes (h+) generated at the Co(II) site as evident from EPR analysis was considered to be responsible for high photocatalytic activity of the material reducing the recombination rate of holes and electrons (e?). Density Functional Theory calculations were performed to understand the mechanism of ethanol oxidation to acetaldehyde.

In Situ Acetaldehyde Synthesis for Carboligation Reactions

The enzyme 4-oxalocrotonate tautomerase (4-OT) can promiscuously catalyze various carboligation reactions using acetaldehyde as a nucleophile. However, the highly reactive nature of acetaldehyde requires intricate handling, which can impede its usage in practical synthesis. Therefore, we investigated three enzymatic routes to synthesize acetaldehyde in situ in one-pot cascade reactions with 4-OT. Two routes afforded practical acetaldehyde concentrations, using an environmental pollutant, trans-3-chloroacrylic acid, or a bio-renewable, ethanol, as starting substrate. These routes can be combined with 4-OT catalyzed Michael-type additions and aldol condensations in one pot. This modular systems biocatalysis methodology provides a stepping stone towards the development of larger artificial metabolic networks for the practical synthesis of important chemical synthons.

Enantioselective Aldol Addition of Acetaldehyde to Aromatic Aldehydes Catalyzed by Proline-Based Carboligases

Aromatic β-hydroxyaldehydes, 1,3-diols, and α,β-unsaturated aldehydes are valuable precursors to biologically active natural products and drug molecules. Herein we report the biocatalytic aldol condensation of acetaldehyde with various aromatic aldehydes to give a number of aromatic α,β-unsaturated aldehydes using a previously engineered variant of 4-oxalocrotonate tautomerase [4-OT(M45T/F50A)] as carboligase. Moreover, an efficient one-pot two-step chemoenzymatic route toward chiral aromatic 1,3-diols has been developed. This one-pot chemoenzymatic strategy successfully combined a highly enantioselective aldol addition step catalyzed by a proline-based carboligase [4-OT(M45T/F50A) or TAUT015] with a chemical reduction step to convert enzymatically prepared aromatic β-hydroxyaldehydes into the corresponding 1,3-diols with high optical purity (e.r. up to >99:1) and in good isolated yield (51-92%). These developed (chemo)enzymatic methodologies offer alternative synthetic choices to prepare a variety of important drug precursors.