52438-21-8

Basic information

• Product Name: 1-cinnamoylpyrrolidine
• Synonyms: 1-cinnamoylpyrrolidine;1-[(2E)-1-Oxo-3-phenyl-2-propenyl]pyrrolidine;Cinnamopyrrolidide
• CAS NO: 52438-21-8
• Molecular Formula: C₁₃H₁₅NO
• Molecular Weight: 201.2643
• Product Categories: Alkaloids
• Mol File: 52438-21-8.mol

Chemical Properties

• Melting Point: 123℃
• Appearance: /
• CAS DataBase Reference: 1-cinnamoylpyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-cinnamoylpyrrolidine(52438-21-8)
• EPA Substance Registry System: 1-cinnamoylpyrrolidine(52438-21-8)

Safety Data

• Hazardous Substances Data: 52438-21-8(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
1-Cinnamoylpyrrolidine is used as a flavoring agent for its distinct aromatic properties, enhancing the taste and scent of various food products.
Used in Tobacco Industry:
1-Cinnamoylpyrrolidine is used as a flavoring component in certain types of tobacco, contributing to their unique and appealing flavor and scent.
Used in Pharmaceutical Research:
1-Cinnamoylpyrrolidine is used as a research compound in the development of new pharmaceuticals, due to its potential to inhibit specific enzymes, which may have therapeutic applications. Further studies are necessary to understand its full potential and safety profile in this context.

Upstream product

• 15097-49-1 N-trimethylsilylpyrrolidine 
• 38986-89-9 trans-cinnamoyl fluoride 
• 123-75-1 pyrrolidine 
• 102-92-1 Cinnamoyl chloride 
• 100-52-7 benzaldehyde 
• 849693-82-9 1-[(diphenylphosphono)acetyl]pyrrolidine 
• 140-10-3 (E)-3-phenylacrylic acid 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 56900-83-5 C₁₉H₃₃AlSi 
• 2033-24-1 cycl-isopropylidene malonate 
• 151647-54-0 3-phenyl-1-pyrrolidin-1-yl-propane-1-one 
• 4030-18-6 N-(acetyl)pyrrolidine 

Downstream Products

• 119163-37-0 ((2S,3R)-3-Phenyl-oxiranyl)-pyrrolidin-1-yl-methanone 
• 185621-76-5 (E)-3-phenyl-1-pyrrolidin-1-yl propenethione 
• 415917-73-6 [(1S,2S,3R)-2-Phenyl-3-((E)-2-trimethylsilanyl-vinyl)-cyclopropyl]-pyrrolidin-1-yl-methanone 
• 389572-81-0 1-{[(2S,3R)-3-phenylaziridin-2-yl]carbonyl}pyrrolidine 
• 198982-11-5 [Ru2(μ-H)(μ-η(3)-PhC=CHC(O)N(CH2)4)(CO)6] 
• 1257558-17-0 3-(4-(1H-pyrrol-1-yl)phenyl)-3-phenyl-1-(pyrrolidin-1-yl)propan-1-one 
• 1257630-49-1 potassium 3-phenyl-1-(pyrrolidin-1-yl)-3-(trifluoroborato)propan-1-one 

Relevant articles and documents

Photoenzymatic Reductions Enabled by Direct Excitation of Flavin-Dependent "Ene"-Reductases

Non-natural photoenzymatic reactions reported to date have depended on the excitation of electron donor-acceptor complexes formed between substrates and cofactors within protein active sites to facilitate electron transfer. While this mechanism has unlocked new reactivity, it limits the types of substrates that can be involved in this area of catalysis. Here we demonstrate that direct excitation of flavin hydroquinone within "ene"-reductase active sites enables new substrates to participate in photoenzymatic reactions. We found that by using photoexcitation these enzymes gain the ability to reduce acrylamides through a single electron transfer mechanism.

Erratum: Photoenzymatic Reductions Enabled by Direct Excitation of Flavin-Dependent 'Ene'-Reductases (J. Am. Chem. Soc. (2021) 143:4 (1735-1739) DOI: 10.1021/jacs.0c11494)

Support by the Department of Energy was inadvertently left out of the Acknowledgments and a coauthor's name was misspelled in the Supporting Information. The scientific part of the manuscript remains unchanged. The complete correct Acknowledgment paragraph is as follows.

Stereoselective formal hydroamidation of si-substituted arylacetylenes with DIBAL-H and isocyanates: Synthesis of (E)- And (Z)-α-Silyl-α,β-unsaturated amides

An efficient and stereoselective method for the synthesis of (E)- and (Z)-α-silyl-α,β-unsaturated amides and its synthetic applications are presented herein. The solvent-controlled hydroaluminations of Si-substituted alkynes with DIBAL-H generate diastereomerically enriched alkenylaluminum reagents that are directly reacted with isocyanates at ambient temperature to afford α-silyl-α,β-unsaturated amides in high yields with retained stereoselectivity. In particular, this process enables the synthesis of a broad range of (E)-α-silyl-α,β- unsaturated amides, which are the less studied isomers. The synthetic utility of this method is highlighted by its short reaction time, ease of purification, easily accessible substrates and reagents, gram-scale synthesis, and the further transformations of C-Si bonds into C-H, C-X, and C-C bonds.

Rapid access to cinnamamides and piper amides: Via three component coupling of arylaldehydes, amines, and Meldrum's acid

A practical method for the synthesis of cinnamamides and piper amides via a conceptually novel three component reaction of aldehydes, amines and Meldrum's acid has been reported. The reaction proceeds under operationally simple conditions without the aid of coupling reagents, oxidants, or catalysts, which are essential for the preparation of cinnamamides/piper amides via known methods. The formation of undesired chemical wastes that generally originate from the use of coupling reagents, oxidants, or catalysts has been avoided to make this reaction more atom economical.

Radical α,β-Dehydrogenation of Saturated Amides via α-Oxidation with TEMPO under Transition Metal-Free Conditions

A transition metal-free radical process for the selective α,β-dehydrogenation of saturated amides under mild conditions is developed. Utilizing radical activation strategy, the challenging issue associated with the low α-acidity of amides is resolved. For the first time, α,β-unsaturated Weinreb amides and acrylamides could be efficiently prepared directly from corresponding saturated amides. Mechanistic studies confirm the radical nature of this transformation. Two gram scale α,β-dehydrogenation have also been performed to demonstrate the utility of this method.

Visible-light-promoted oxidation/condensation of benzyl alcohols with dialkylacetamides to cinnamides

Oxidative cross-coupling reactions of benzyl alcohols with N,N-dialkylacetamides were developed only employing oxygen as the terminal oxidant, efficiently providing a new, novel protocol for the construction of multifunctionalized cinnamides with the synergistic effects of KOH, organic photocatalyst eosin Y, and visible light irradiation at room temperature. A broad substrate scope and mild reaction conditions are the prominent features of this transformation.

Enantioselective Epoxidation of Electron-Deficient Alkenes Catalyzed by Manganese Complexes with Chiral N4 Ligands Derived from Rigid Chiral Diamines

A series of tetradentate sp2N/sp3N hybrid chiral N4 ligands derived from rigid chiral diamines were synthesized, which enabled the first manganese-catalyzed enantioselective epoxidation of electron-deficient alkenes with hydrogen peroxide (H2O2) as an oxidant. The reaction furnishes enantiomerically pure epoxy amides, epoxy ketones as well as epoxy esters in good yields and excellent enantioselectivities (up to 99.9% ee) with lower catalyst loading. Preliminary studies on structure–activity relationship demonstrated that maintaining comparatively lower electron-donating ability of the sp3N and relatively higher electron-donating ability of sp2N of the N4 ligands is beneficial to getting higher activity and selectivity, thus providing us a new view to understand epoxidation with H2O2. (Figure presented.).

General and Efficient Intermolecular [2+2] Photodimerization of Chalcones and Cinnamic Acid Derivatives in Solution through Visible-Light Catalysis

[2+2] Photocycloaddition, for example, the dimerization of chalcones and cinnamic acid derivatives, is a unique strategy to construct cyclobutanes, which are building blocks for a variety of biologically active molecules and natural products. However, most attempts at the above [2+2] addition have focused on solid-state, molten-state, or host–guest systems under ultraviolet-light irradiation in order to overcome the competition of facile geometric isomerization of nonrigid olefins. We report a general and simple method to realize the intermolecular [2+2] dimerization reaction of these acyclic olefins to construct cyclobutanes in a highly regio- and diastereoselective manner in solution under visible light, which provides an efficient solution to a long-standing problem.

Borane-Catalyzed Reductive α-Silylation of Conjugated Esters and Amides Leaving Carbonyl Groups Intact

Described herein is the development of the B(C6F5)3-catalyzed hydrosilylation of α,β-unsaturated esters and amides to afford synthetically valuable α-silyl carbonyl products. The α-silylation occurs chemoselectively, thus leaving the labile carbonyl groups intact. The reaction features a broad scope of both acyclic and cyclic substrates, and the synthetic utility of the obtained α-silyl carbonyl products is also demonstrated. Mechanistic studies revealed two operative steps: fast 1,4-hydrosilylation of conjugated carbonyls and then slow silyl group migration of a silyl ether intermediate.

Amides in one pot from Carboxylic Acids and Amines via Sulfinylamides

An efficient method has been developed for the direct amidification of carboxylic acids via sulfinylamides preformed in situ by the reaction of pure amines with prop-2- ene-1-sulfinyl chloride. The method can be applied to aliphatic acids, including pivalic acid, aromatic acids, and primary and secondary amines. It is compatible with acids bearing unprotected alcohol, phenol, and ketone moieties and applicable to the synthesis of peptides. It does not induce their a-epimerization.