4432-63-7

Basic information

• Product Name: Atropaldehyde
• Synonyms: Atropaldehyde;2-Phenyl-2-propene-1-al;2-Phenylacrylaldehyde;2-Phenylpropenal;Benzeneacetaldehyde, .alpha.-Methylene-
• CAS NO: 4432-63-7
• Molecular Formula: C₉H₈O
• Molecular Weight: 132.15922
• Mol File: 4432-63-7.mol

Chemical Properties

• Boiling Point: 260 °C at 760 mmHg
• Flash Point: 86.5 °C
• Appearance: /
• Density: 0.996 g/cm³
• CAS DataBase Reference: Atropaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: Atropaldehyde(4432-63-7)
• EPA Substance Registry System: Atropaldehyde(4432-63-7)

Safety Data

• Hazardous Substances Data: 4432-63-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Atropaldehyde is used as a precursor for the synthesis of atropine, which is a medication for treating nerve agent and pesticide poisonings, as well as certain types of slow heart rate. It also helps in decreasing secretions such as saliva and stomach acid.
Atropaldehyde is used as a research compound for exploring its potential therapeutic uses in the treatment of disorders related to the nervous system and muscle function. Its involvement in the regulation of various bodily functions makes it a promising candidate for developing new drugs and treatments for various medical conditions.
Used in Medical Research:
Atropaldehyde is used as a subject of research in the medical field to understand its role in the regulation of bodily functions and its potential applications in the development of new drugs and treatments for various medical conditions. Its connection to acetylcholine, a neurotransmitter, makes it an interesting area of study for scientists working on nervous system-related disorders and muscle function.

Upstream product

• 50-00-0 formaldehyd 
• 122-78-1 phenylacetaldehyde 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 2327-99-3 1-phenylpropadiene 
• 6006-81-1 3-hydroxy-2-phenylpropene 
• 129665-64-1 2-phenyl-3-tosyl-1-propanol 
• 75700-24-2 3-phenyloxete 
• 121034-40-0 2-Phenyl-2-phenylselanyl-propionaldehyde 
• 98-83-9 isopropenylbenzene 
• 80234-04-4 2-phenylacrylaldehyde diethyl acetal 
• 25451-53-0 2-phenyl-1,3-propanediol monocarbamate 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 
• 2415-80-7 1,1-dichloro-2-phenylcyclopropane 

Downstream Products

• 1125-70-8 2-phenylpropanamide 
• 132356-38-8 3,4-dihydro-2-hydroxy-3-phenyl-2H,5H-pyrano<3,2-c><1>benzopyran-5-one 
• 345929-47-7 2-Nitro-2-(3-oxo-2-phenyl-propyl)-malonic acid dimethyl ester 
• 97728-02-4 2-phenyl-1-hexen-5-yn-3-ol 
• 53847-12-4 2-phenyl-1,5-hexadien-3-ol 
• 149379-74-8 2-methoxy-5-phenylpyridine-3-carbonitrile 
• 149379-78-2 2-amino-5-phenylbenzene-1,3-dicarbonitrile 
• 6006-81-1 3-hydroxy-2-phenylpropene 
• 162660-52-8 4-methyl-4-nitro-2-phenylvaleraldehyde 
• 162660-53-9 4-(dioxolan-2-yl)-2-methyl-2-nitro-4-phenylbutane 
• 53847-15-7 5-phenylhexa-1,5-dien-3-ol 
• 178817-64-6 [1-2H]-2-phenyl-2-propen-1-ol 
• 78593-99-4 2-Phenyl-3-phenylsulfanyl-propionaldehyde 

Relevant articles and documents

Synthesis of the cis diastereoisomer of 5-diethoxyphosphoryl-5-methyl-3- phenyl-1-pyrroline N-oxide (DEPMPPOc) and ESR study of its superoxide spin adduct

The cis and trans diastereoisomers of 5-diethoxyphosphoryl-5-methyl-3- phenyl-1-pyrroline N-oxide (DEPMPPO), the C(3)-phenyl analogue of DEPMPO, were prepared in three steps from phenylacetaldehyde and used in ESR-spin trapping of various carbon-, oxygen- and sulfur-centred radicals. In the case of the cis-isomer, the presence of the phenyl group cancels the alternating line width phenomenon observed for the DEPMPO-OOR (R = H, But) spin adducts. The ESR spectra of the DEPMPPOc-OOR spin adducts exhibit more straightforward patterns and are more easily assignable.

Role of glutathione S-transferases A1-1, M1-1, and P1-1 in the detoxification of 2-phenylpropenal, a reactive felbamate metabolite

Felbamate has proven to be an effective therapy for treating refractory epilepsy. However, felbamate therapy has been limited due to the associated reports of hepatotoxicity and aplastic anemia. Previous research from our laboratory has proposed 2-phenylpropenal as the reactive metabolite in felbamate bioactivation and identified its mercapturates in the urine of rats and patients undergoing felbamate therapy. While the reaction between 2-phenylpropenal and GSH has been shown to occur spontaneously under physiological conditions, the potential catalysis by glutathione transferases (GST) has remained unknown. The work presented here demonstrates a role for GST in the detoxification of 2-phenylpropenal. The kinetic data show that 2-phenylpropenal is a substrate for all three isoforms tested, with a kcat/Km of 0.275 ± 0.035 μM-1 s-1 for GSTM1-1, 0.164 ± 0.005 μM-1 s-1 for GSTP1-1, and 0.042 ± 0.005 μM-1 s-1 for GSTA1-1. Given that electrophilic substrates such as 2-propenal have been shown to inhibit GSTs, we also examined the inhibition of GSTM1-1, GSTP1-1 and GSTA1-1 by 2-phenylpropenal. The enzyme inhibition studies demonstrate that 2-phenylpropenal inhibits GSTP1-1 and GSTM1-1. The inhibition of GSTP1-1 was completely reversible upon filtration and reconstitution in buffer containing 10 mM GSH. However, 2-phenylpropenal inhibition of GSTM1-1 was irreversible under the same conditions. The irreversible inhibition of GSTM1-1 may be important in understanding the toxicities associated with felbamate. Given that 2-phenylpropenal is both a substrate and irreversible inhibitor for GSTM1-1, GSTM1-1 represents a potential target for 2-phenylpropenal haptenization in vivo, which may in turn mediate the observed idiosyncratic reactions.

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.

Rhodium-Catalyzed Regio- And Enantioselective Allylic Amination of Racemic 1,2-Disubstituted Allylic Phosphates

Alkynylphosphines are rarely used as ligands in asymmetric metal catalysis. We synthesized a series of chiral bis(oxazoline)alkynylphosphine ligands and used them in Rh-catalyzed highly regio- and enantioselective allylic amination reactions of 1,2-disubstituted allylic phosphates. Chiral 1,2-disubstituted allylic amines were synthesized in up to 95% yield with >20:1 branched/linear (b/l) ratio and 99% ee from racemic 1,2-disubstituted allylic precursors. The sterically smaller linear alkynyl group on the P atom in the bis(oxazoline)alkynylphosphine ligands was the key to fit the new requirements of the introduction of bulky 2-R′ groups.

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.

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.

Two C=C Bond Participation in Annulation to Pyridines Based on DMF as the Nonadjacent N and C Atom Donors

Two C=C bond participation in annulation to pyridines using N,N-dimethylformamide (DMF) as the N1 and C4 synthons has been carried out. In this reaction, DMF contributed one N atom and one C atom to two disconnected positions of pyridine ring, with no need for an additional nitrogen source. Two C=C bonds in two molecules of substituted styrenes offered four carbon atoms in the presence of iodine and persulfate. With the optimized conditions in hand, both symmetric and unsymmetric diaryl-substituted pyridines were obtained in useful yields. On the basis of relevant literature and a series of control experimental results, a possible mechanism was proposed in this work, which may demonstrate how DMF provides both N1 and C4 sources.

Formal Enone α-Arylation via I(III)-Mediated Aryl Migration/Elimination

A formal enone α-arylation is described. This metal-free transformation relies on the I(III)-mediated skeletal reorganization of silyl enol ethers and features mild conditions, good yields, and high stereoselectivities for β-substituted enones.

Modular Synthesis of α-Substituted Alkenyl Acetals by a Palladium-Catalyzed Suzuki Reaction of α-Haloalkenyl Acetals with Organoboranes

A modular and straightforward synthetic strategy for the preparation of α-substituted alkenyl acetals has been developed. α-Haloalkenyl acetals react smoothly with (het)aryl boronic acids, aryl boronates, or B-Alkyl-9-borabicyclo[3.3.1]nonanes through Pd-catalyzed Suzuki cross-coupling under mild conditions with good to high yields. This protocol features a broad substrate scope and good functional-group compatibility, and is easily scaled up.

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.