40832-99-3

Usage

Uses

Used in Pharmaceutical Research and Development:
1-Phenylazepane is used as a synthetic intermediate for the development of pharmaceuticals, leveraging its structural features to create new compounds with potential therapeutic applications.
Used in Organic Chemistry:
As a member of the azepane family, 1-Phenylazepane is utilized as a key intermediate in organic synthesis, contributing to the formation of various complex organic molecules through its reactive sites and structural attributes.
Used in Medicinal Chemistry:
1-Phenylazepane is employed as a structural motif in medicinal chemistry for the design and synthesis of novel drug candidates, potentially leading to the discovery of new therapeutic agents with improved pharmacological properties.
While the specific biological effects and pharmacological applications of 1-phenylazepane have not been extensively studied, its role in the synthesis of pharmaceuticals and its potential as a structural motif in medicinal chemistry highlight its importance in the development of new chemical entities with therapeutic potential.

InChI:InChI=1/C12H17N/c1-2-7-11-13(10-6-1)12-8-4-3-5-9-12/h3-5,8-9H,1-2,6-7,10-11H2

Upstream product

• 111-49-9 hexamethylene imine 
• 592-90-5 oxepane 
• 62-53-3 aniline 
• 629-03-8 1 ,6-dibromohexane 
• 127395-14-6 Bis-benzotriazol-1-ylmethyl-phenyl-amine 
• 23708-47-6 1,4-bis(bromomagnesium)butane 
• 108-90-7 chlorobenzene 
• 4920-92-7 pivalic acid phenyl ester 
• 629-11-8 1,6-hexanediol 
• 591-50-4 iodobenzene 
• 19858-02-7 N-Phenylhexahydroazepin-2-on 
• 58028-75-4 2-(Perhydroazepin-1-yl)benzaldehyd 
• 446-52-6 2-Fluorobenzaldehyde 
• 28493-41-6 N-chloroperhydroazepine 

Downstream Products

• 131998-62-4 4-(Hexahydroazepinyl)benzenesulphonyl chloride 
• 131998-61-3 1-[4-(1-hexahydroazepinyl)benzenesulphonyl]-2-pyrrolidinone 
• 131998-67-9 1-[4-(1-hexahydroazepinyl)benzenesulphonyl]-2-piperidinone 
• 1026950-55-9 4-(4-Azepan-1-yl-benzenesulfonylamino)-butyric acid 
• 131998-65-7 5-[4-(1-Hexahydroazepinyl)benzenesulphonylamino]valeric acid 
• 855710-85-9 7-(N-cyano-anilino)-heptanenitrile 
• 1221276-55-6 C₂₀H₂₂N₂O₂ 
• 1781301-15-2 1-phenylpiperidine-2-carbaldehyde 

Relevant academic research and scientific papers

Organic photoredox catalytic α-C(sp3)-H phosphorylation of saturated: Aza -heterocycles

A metal-free C(sp3)-H phosphorylation of saturated aza-heterocycles via the merger of organic photoredox and Br?nsted acid catalyses was established under mild conditions. This protocol provided straightforward and economic access to a variety of valuable α-phosphoryl cyclic amines by using commercially available diarylphosphine oxide reagents. In addition, the D-A fluorescent molecule DCQ was used for the first time as a photocatalyst and exhibited an excellent photoredox catalytic efficiency in this transformation. A series of mechanistic experiments and DFT calculations demonstrated that this transformation underwent a sequential visible light photoredox catalytic oxidation/nucleophilic addition process.

Electron Donor-Acceptor Complex-Initiated Photochemical Cyanation for the Preparation of α-Amino Nitriles

An electron donor-acceptor complex-initiated α-cyanation of tertiary amines has been described. The reaction protocol provides a novel method to synthesize various α-amino nitriles under mild conditions. The reaction can proceed smoothly without the presence of photocatalysts and transition metal catalysts, and either oxidants are unnecessary or O2 is the only oxidant. The practicality of this method is showcased not only by the late-stage functionalization of natural alkaloid derivatives and pharmaceutical intermediate, but also by the applicability of a stop-flow microtubing reactor.

Catalyst-free photodecarbonylation ofortho-amino benzaldehyde

It is almost a consensus that decarbonylation of the aldehyde group (-CHO) needs to not only be mediated by transition metal catalysts, but also requires severe reaction conditions (high temperature and long reaction time). In this work, inspired by the “conformational-selectivity-based” design strategy, we broke this consensus and discovered a catalyst-free photodecarbonylation of the aldehyde group. It revealed that decarbonylation can be easily achieved with visible light irradiation by introducing a tertiary amine into theortho-position of the aldehyde group. A diverse array of tertiary amines is tolerated by our photodecarbonylation under mild conditions. Furthermore, the (QM) computations of the mechanism and the experiments on well-designed special substrates revealed that our photodecarbonylation depends on the conformational specificity of the aldehyde group and tertiary amine, and occurs through an unusual [1,4]-H shift and a subsequent [1,3]-H shift.

Robust Buchwald-Hartwig amination enabled by ball-milling

An operationally simple mechanochemical method for the Pd catalysed Buchwald-Hartwig amination of arylhalides with secondary amines has been developed using a Pd PEPPSI catalyst system. The system is demonstrated on 30 substrates and applied in the context of a target synthesis. Furthermore, the performance of the reaction under aerobic conditions has been probed under traditional solution and mechanochemical conditions, the observations are discussed herein.

Metal-Free Synthesis of N-Aryl-Substituted Azacycles from Cyclic Ethers Using POCl3

A facile method for the synthesis of N-aryl-substituted azacycles from arylamines and cyclic ethers has been developed. In this study, arylamines were treated with cyclic ethers in the presence of POCl3 and DBU to provide five- A nd six-membered azacycles. Using this method, various azacycloalkanes, isoindolines, and tetrahydroisoquinolines were prepared in high yields. This synthetic method offers an efficient approach to the production of azacycles from cyclic ethers.

Practical and regioselective amination of arenes using alkyl amines

The formation of carbon–nitrogen bonds for the preparation of aromatic amines is among the top five reactions carried out globally for the production of high-value materials, ranging from from bulk chemicals to pharmaceuticals and polymers. As a result of this ubiquity and diversity, methods for their preparation impact the full spectrum of chemical syntheses in academia and industry. In general, these molecules are assembled through the stepwise introduction of a reactivity handle in place of an aromatic C–H bond (that is, a nitro group, halogen or boronic acid) and a subsequent functionalization or cross-coupling. Here we show that aromatic amines can be constructed by direct reaction of arenes and alkyl amines using photocatalysis, without the need for pre-functionalization. The process enables the easy preparation of advanced building blocks, tolerates a broad range of functionalities, and multigram scale can be achieved via a batch-to-flow protocol. The merit of this strategy as a late-stage functionalization platform has been demonstrated by the modification of several drugs, agrochemicals, peptides, chiral catalysts, polymers and organometallic complexes.

Efficient nickel-catalysed: N -alkylation of amines with alcohols

The selective N-alkylation of amines with alcohols via the borrowing hydrogen strategy represents a prominent sustainable catalytic method, which produces water as the only by-product and is ideally suited for the catalytic transformation of widely available alcohol reaction partners that can be derived from renewable resources. Intensive research has been devoted to the development of novel catalysts that are mainly based on expensive noble metals. However, the availability of homogeneous or heterogeneous non-precious metal catalysts for this transformation is very limited. Herein we present a highly active and remarkably easy-to-prepare Ni based catalyst system for the selective N-alkylation of amines with alcohols, that is in situ generated from Ni(COD)2 and KOH under ligand-free conditions. This novel method is very efficient for the functionalization of aniline and derivatives with a wide range of aromatic and aliphatic alcohols as well as diols and exhibits excellent functional group tolerance including halides, benzodioxane and heteroaromatic groups. Several TEM measurements combined with elemental analysis were conducted in order to gain insight into the nature of the active catalyst and factors influencing reactivity.

Nickel-Catalyzed Reductive Cleavage of Carbon-Oxygen Bonds in Anisole Derivatives Using Diisopropylaminoborane

The catalytic removal of a methoxy group on an aromatic ring allows this group to be used as a traceless activating and directing group for aromatic functionalization reactions. Although several catalytic methods for the reductive cleavage of anisole derivatives have been reported, all are applicable only to π-extended aryl ethers, such as naphthyl and biphenyl ethers, while monocyclic aryl ethers cannot be reduced. Herein, we report a nickel-catalyzed reductive cleavage reaction of C-O bonds in aryl ethers using diisopropylaminoborane as the reducing agent. Unlike previously reported methods, this reducing reagent allows effective C-O bond reduction in a much wider range of aryl ether substrates, including monocyclic and heterocyclic ethers bearing various functional groups.

Dual C(sp3)?H Bond Functionalization of N-Heterocycles through Sequential Visible-Light Photocatalyzed Dehydrogenation/[2+2] Cycloaddition Reactions

Herein we describe a mild method for the dual C(sp3)?H bond functionalization of saturated nitrogen-containing heterocycles through a sequential visible-light photocatalyzed dehydrogenation/[2+2] cycloaddition procedure. As a complementary approach to the well-established use of iminium ion and α-amino radical intermediates, the elusive cyclic enamine intermediates were effectively generated by photoredox catalysis under mild conditions and efficiently captured by acetylene esters to form a wide array of bicyclic amino acid derivatives, thus enabling the simultaneous functionalization of two vicinal C(sp3)?H bonds.

A new route to N-aromatic heterocycles from the hydrogenation of diesters in the presence of anilines

The hydrogenation of dicarboxylic acids and their esters in the presence of anilines provides a new synthesis of heterocycles. [Ru(acac)3] and 1,1,1-tris(diphenylphosphinomethyl)ethane (triphos) gave good to excellent yields of the cyclic amines at 220 °C. When aqueous ammonia was used with dimethyl 1,6-hexadienoic acid, ?-caprolactam was obtained in good yield. A side reaction involving alkylation of the amine by methanol was suppressed by using diesters derived from longer chain and branched alcohols. Hydrogenation of optically pure diesters (dimethyl (R)-2-methylbutanedioate and dimethyl (S)-2-methylbutanedioate) with aniline afforded racemic 3-methyl-1-phenylpyrrolidine in 78% yield.