16619-19-5

Usage

Uses

Used in Pharmaceutical Industry:
4-(1-oxo-3-phenylallyl)morpholine is used as an intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of various medicinal compounds.
Used in Agrochemical Industry:
4-(1-oxo-3-phenylallyl)morpholine is used as an intermediate in the synthesis of agrochemicals, playing a role in the creation of substances that can enhance crop protection and productivity.
It is important to handle 4-(1-oxo-3-phenylallyl)morpholine with care, as it may have harmful effects on human health and the environment.

InChI:InChI=1/C13H15NO2/c15-13(14-8-10-16-11-9-14)7-6-12-4-2-1-3-5-12/h1-7H,8-11H2/b7-6+

Upstream product

• 110-91-8 morpholine 
• 102-92-1 Cinnamoyl chloride 
• 621-82-9 Cinnamic acid 
• 798044-45-8 3-(2,3-dichlorophenyl)-3-phenylpropionamide 
• 101132-14-3 2-morpholin-4-yl-4-phenyl-but-3-enenitrile 
• 140-10-3 (E)-3-phenylacrylic acid 
• 328012-09-5 (E)-1-(1H-benzo[d][1,2,3]triazol-1-yl)-3-phenylprop-2-en-1-one 
• 102-92-1 cinnamoyl chloride 
• 39205-49-7 2,2-dichloro-1-morpholinoethan-1-one 
• 100-52-7 benzaldehyde 
• 621-79-4 cinnamamide 
• 40299-87-4 N-(bromoacetyl)morpholine 
• 4885-64-7 1-morpholin-4-yl-2-(triphenyl-phosphanylidene)-ethanone 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 

Downstream Products

• 37935-65-2 4-(3-phenyl-3-trimethylsilanyl-propionyl)-morpholine 
• 17077-46-2 4-(3-phenyl-propionyl)-morpholine 
• 134715-42-7 3-(3-Morpholin-4-yl-5-phenyl-4,5-dihydro-pyrazol-1-yl)-3-oxo-N-p-tolyl-propionamide 
• 134715-40-5 3-(3-Morpholin-4-yl-5-phenyl-4,5-dihydro-pyrazol-1-yl)-3-oxo-N-o-tolyl-propionamide 
• 134715-41-6 3-(3-Morpholin-4-yl-5-phenyl-4,5-dihydro-pyrazol-1-yl)-3-oxo-N-m-tolyl-propionamide 
• 134715-30-3 4-<3'-(1'-anilinomalonyl-5'-phenyl)pyrazolinyl>morpholine 
• 134715-46-1 N-(4-Chloro-phenyl)-3-(3-morpholin-4-yl-5-phenyl-4,5-dihydro-pyrazol-1-yl)-3-oxo-propionamide 
• 134715-44-9 N-(2-Chloro-phenyl)-3-(3-morpholin-4-yl-5-phenyl-4,5-dihydro-pyrazol-1-yl)-3-oxo-propionamide 
• 134715-45-0 N-(3-Chloro-phenyl)-3-(3-morpholin-4-yl-5-phenyl-4,5-dihydro-pyrazol-1-yl)-3-oxo-propionamide 
• 134715-43-8 N-(2-Methoxy-phenyl)-3-(3-morpholin-4-yl-5-phenyl-4,5-dihydro-pyrazol-1-yl)-3-oxo-propionamide 
• 19184-21-5 (E)-1-phenylhept-1-en-3-one 
• 38661-84-6 (E)-1,4-diphenylbut-1-en-3-one 
• 147599-28-8 4-((2R,3R)-5-oxo-3-phenyltetrahydrofuran-2-yl)benzonitrile 
• 897392-13-1 morpholin-4-yl-(2-phenyl-3-styryl-cyclopropyl)-methanone 

Relevant academic research and scientific papers

Design of enamides as new selective monoamine oxidase-B inhibitors

Objectives: To develop of new class of selective and reversible MAO-B inhibitors from enamides. Methods: Syntheses of the titled derivatives (AD1–AD11) were achieved by reacting cinnamoyl chloride and various primary and secondary amines in basic medium. All eleven compounds were investigated for in vitro inhibitory activities against recombinant human MAO-A and MAO-B. The reversibilities of lead compound inhibitions were analysed by dialysis. MTT assays of lead compounds were performed using normal VERO cell lines. Key findings: Compounds AD3 and AD9 exhibited the greatest inhibitory activity against MAO-B with IC50 values of 0.11 and 0.10?μm, respectively, and were followed by AD2 and AD1 (0.51 and 0.71?μm, respectively). Most of the compounds weakly inhibited MAO-A, with the exceptions AD9 and AD7, which had IC50 values of 4.21 and 5.95?μm, respectively. AD3 had the highest selectivity index (SI) value for MAO-B (>363.6) and was followed by AD9 (SI 42.1). AD3 and AD9 were found to be competitive inhibitors of MAO-B with Ki values of 0.044?±?0.0036 and 0.039?±?0.0047?μm, respectively. Reversibility experiments showed AD3 and AD9 were reversible inhibitors of MAO-B; dialysis restored the activity of MAO-B to the reference level. MTT assays revealed AD3 and AD9 were non-toxic to normal VERO cell lines with IC50 values of 153.96 and 194.04?μg/ml, respectively. Computational studies provided hypothetical binding modes for AD3 and AD9 in the binding cavities of MAO-A and MAO-B. Conclusions: These results encourage further studies on the enamide scaffold as potential drug candidates for the treatment of Alzheimer's and Parkinson's diseases.

Dialkylaminoacetonitrile Derivatives as Amide Synthons. A One-Pot Preparation of Heteroaryl Amides via a Strategy of Sequential SNAr Substitution and Oxidation

Dialkylamino acetonitrile derivatives were utilized as alternative to cyanohydrin synthons for preparation of the corresponding heteroaryl dialkyl amides via a strategy of sequential base-mediated coupling and oxidation. The most advantageous oxidant, NiO2-H2O, can readily oxidize 2-substituted aminoacetonitriles to the corresponding amides under both basic and neutral conditions by forming cyanohydrins in situ.

PCl3-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation

A PCl3-mediated conversion of tert-butyl esters into esters and amides in one-pot under air is developed. This novel protocol is highlighted by the synthesis of skeletons of bioactive molecules and gram-scale reactions. Mechanistic studies revealed that this transformation involves the formation of an acid chloride in situ, which is followed by reactions with alcohols or amines to afford the desired products.

Electron-Catalyzed Aminocarbonylation: Synthesis of α,β-Unsaturated Amides from Alkenyl Iodides, CO, and Amines

Aminocarbonylation of alkenyl iodides with CO and amines proceeded under heating to produce α,β-unsaturated amides in good yields (23 examples, 71% average yield). This catalyst-free method exhibited good functional-group tolerance, and open a straightforward access to functionalized acrylamides, as illustrated by the synthesis of Ilepcimide. A hybrid radical/ionic mechanism involving chain electron transfer is proposed for this transformation.

Direct Amidation of Esters by Ball Milling**

The direct mechanochemical amidation of esters by ball milling is described. The operationally simple procedure requires an ester, an amine, and substoichiometric KOtBu and was used to prepare a large and diverse library of 78 amide structures with modest to excellent efficiency. Heteroaromatic and heterocyclic components are specifically shown to be amenable to this mechanochemical protocol. This direct synthesis platform has been applied to the synthesis of active pharmaceutical ingredients (APIs) and agrochemicals as well as the gram-scale synthesis of an active pharmaceutical, all in the absence of a reaction solvent.

Mizoroki-Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C-C Bond Olefination

Mizoroki-Heck reaction of unstrained aryl ketone with acrylate/styrene is accomplished via palladium-catalyzed ligand-promoted C-C bond cleavage. Various (hetero)aryl ketones are compatible in the reaction, affording the alkene product in good to excellent yields. Further applications in the late-stage olefination of some drugs, natural products, and fragrance-derived aryl ketones demonstrate the synthetic utility of this protocol. By employing ketone as both the directing group and the leaving group, 1,2-bifunctionalization is achieved via sequential ortho-C-H alkylation/ipso-Heck olefination.

Selective Construction of C?C and C=C Bonds by Manganese Catalyzed Coupling of Alcohols with Phosphorus Ylides

Herein, we report the manganese catalyzed coupling of alcohols with phosphorus ylides. The selectivity in the coupling of primary alcohols with phosphorus ylides to form carbon-carbon single (C?C) and carbon-carbon double (C=C) bonds can be controlled by the ligands. In the conversion of more challenging secondary alcohols with phosphorus ylides the selectivity towards the formation of C?C vs. C=C bonds can be controlled by the reaction conditions, namely the amount of base. The scope and limitations of the coupling reactions were thoroughly evaluated by the conversion of 21 alcohols and 15 ylides. Notably, compared to existing methods, which are based on precious metal complexes as catalysts, the present catalytic system is based on earth abundant manganese catalysts. The reaction can also be performed in a sequential one-pot reaction generating the phosphorus ylide in situ followed manganese catalyzed C?C and C=C bond formation. Mechanistic studies suggest that the C?C bond was generated via a borrowing hydrogen pathway and the C=C bond formation followed an acceptorless dehydrogenative coupling pathway. (Figure presented.).

Simple Synthesis of Amides via Their Acid Chlorides in Aqueous TPGS-750-M

The technology of surfactant chemistry is employed for amide bond construction via the reaction of acyl chlorides with amines in 2 wt % TPGS-750-M aqueous solution. Specifically, this highly efficient method enables a chromatography-free scalable process and recycling of the TPGS-750-M solution.

Catalytic α-Hydroarylation of Acrylates and Acrylamides via an Interrupted Hydrodehalogenation Reaction

The palladium-catalyzed, α-selective hydroarylation of acrylates and acrylamides is reported. Under optimized conditions, this method is highly tolerant of a wide range of substrates including those with base sensitive functional groups and/or multiple enolizable carbonyl groups. A detailed mechanistic study was undertaken, and the high selectivity of this transformation was shown to be enabled by the formation of a [PdII(Ar)(H)] intermediate, which performs selective hydride insertion into the β-position of α,β-unsaturated carbonyl compounds.

Copper(I)-Catalyzed Asymmetric 1,4-Conjugate Hydrophosphination of α,β-Unsaturated Amides

A catalytic asymmetric conjugate hydrophosphination of α,β-unsaturated amides is accomplished by virtue of the strong nucleophilicity of copper(I)-PPh2 species, which provides an array of chiral phosphines bearing an amide moiety in high to excellent yields with excellent enantioselectivity. Furthermore, the dynamic kinetic resolution of unsymmetrical diarylphosphines (HPAr1Ar2) is successfully carried out through the copper(I)-catalyzed conjugate addition to α,β-unsaturated amides, which affords P-chiral phosphines with good-to-high diastereoselectivity and high enantioselectivity. 1H NMR studies show that the precoordination of HPPh2 to copper(I)-bisphosphine complex is critical for the efficient deprotonation by Barton's Base. Moreover, the relative stability of the copper(I)-(R,RP)-TANIAPHOS complex in the presence of excessive HPPh2, confirmed by 31P NMR studies, is pivotal for the high asymmetric induction, as the ligand exchange between bisphosphine and HPPh2 would significantly reduce the enantioselectivity. At last, a double catalytic asymmetric conjugate hydrophosphination furnishes the corresponding product in high yield with high diastereoselectivity and excellent enantioselectivity, which is transformed to a chiral pincer palladium complex in moderate yield. This chiral palladium complex is demonstrated as an excellent catalyst in the asymmetric conjugate hydrophosphination of chalcone.