4108-58-1

Usage

Chemical Properties

White to off-white powder

InChI:InChI=1/C15H15NO/c1-12(13-8-4-2-5-9-13)16-15(17)14-10-6-3-7-11-14/h2-12H,1H3,(H,16,17)/t12-/m0/s1

Upstream product

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 98-88-4 benzoyl chloride 
• 159717-45-0 (R)-N-(2-chloro-1-phenylethyl)benzamide 
• 618-36-0 rac-methylbenzylamine 
• 404942-41-2 [(3aS,8aR)-3-benzoyl-3,3a,8,8a-tetrahydro-2H-indenol[1,2-d][1,3]oxazol-2-ylidene]cyanamide 
• 17279-30-0 (S)-(-)-α-methylbenzylamine hydrochloride 
• 7782-24-3 (S)-2-Phenylpropionic acid 
• 65-85-0 benzoic acid 
• 78798-33-1 (S)-N-hydroxy-α-methyl-benzenemethanamine ethanedioate 
• 611-73-4 Benzoylformic acid 
• 35474-20-5 N-chloro-α-methylbenzylamine 
• 100-52-7 benzaldehyde 
• 42157-97-1 1-bromo-1-phenyl-nitromethane 
• 451-40-1 phenyl benzyl ketone 

Downstream Products

• 100-47-0 benzonitrile 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 1297595-41-5 (S)-N-(1-phenylethyl)benzimidoyl chloride 
• 100969-25-3 N-nitroso-N-((S)-1-phenyl-ethyl)-benzamide 
• 17480-69-2 (S)-N-benzyl-1-phenylethylamine 

Relevant academic research and scientific papers

AMINE-BORANES AS BIFUNCTIONAL REAGENTS FOR DIRECT AMIDATION OF CARBOXYLIC ACIDS

The present invention generally relates to a process for selective and direct activation and subsequent amidation of aliphatic and aromatic carboxylic acids to afford an amide R3CONR1R2. That the process is capable of delivering gaseous or low-boiling point amines provides a major advantage over existing methodologies, which involves an intermediate of triacyloxyborane-amine complex [(R3CO2)3—B—NHR1R2]. This procedure readily produces primary, secondary, and tertiary amides, and is compatible with the chirality of the acid and amine involved. The preparation of known pharmaceutical molecules and intermediates has also been demonstrated.

Generation of Oxyphosphonium Ions by Photoredox/Cobaloxime Catalysis for Scalable Amide and Peptide Synthesis in Batch and Continuous-Flow

Phosphine-mediated deoxygenative nucleophilic substitutions, such as the Mitsunobu reaction, are of great importance in organic synthesis. However, the conventional protocols require stoichiometric oxidants to trigger the formation of the oxyphosphonium i

Direct enantioseparation of axially chiral 1,1′-biaryl-2,2′-diols using amidine-based resolving agents

Amidine-based optically active resolving agents for enantiomer separation of axially chiral 1,1′-biaryl-2,2′-diols have been developed. A strongly basic amidine bearing no substituents on its nitrogen atoms enables the formation of their diastereomeric salts upon being mixed with weakly acidic phenol derivatives. Enantiopure 1,1′-biaryl-2,2′-diols can be obtained in high yields after only one crystallization of their salts with the chiral amidine derived from dehydroabietic acid. X-ray crystallography revealed that the amidine moiety forms a salt with the phenol group and additional intermolecular NH/π interactions contribute to the efficient chiral recognition process.

Design and synthesis of 3,3′-triazolyl biisoquinoline N,N’-dioxides via Hiyama cross-coupling of 4-trimethylsilyl-1,2,3-triazoles

A new strategy to effectively lock the conformation of substituents at the 3,3′-positions of axial-chiral biisoquinoline N,N’-dioxides was developed based on the strong dipole–dipole interaction between 1,2,3-triazole and pyridine N-oxide rings. The crystal structure and the DFT calculations of 3,3′-bis(1-benzyl-1H-1,2,3-triazole-4-yl)-1,1′-biisoquinoline N,N’-dioxide (3a) provided strong support for this strategy. Furthermore, we successfully demonstrated that readily available 4-trimethylsilyl-1,2,3-triazoles are viable nucleophiles for Hiyama cross-coupling.

Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP)

This work describes the application of pentafluoropyridine (PFP), a cheap commercially available reagent, in the deoxyfluorination of carboxylic acids to acyl fluorides. The acyl fluorides can be formed from a range of acids under mild conditions. We also demonstrate that PFP can be utilized in a one-pot amide bond formation via in situ generation of acyl fluorides. This one-pot deoxyfluorination amide bond-forming reaction gives ready access to amides in yields of ≤94%.

Regio- And Stereoselective (S N2) N -, O -, C - And S -Alkylation Using Trialkyl Phosphates

Bimolecular nucleophilic substitution (S N 2) is one of the most well-known fundamental reactions in organic chemistry to generate new molecules from two molecules. In principle, a nucleophile attacks from the back side of an alkylating agent having a suitable leaving group, most commonly a halide. However, alkyl halides are expensive, very harmful, toxic and not so stable, which makes them problematic for laboratory use. In contrast, trialkyl phosphates are inexpensive, readily accessible and stable at room temperature, under air, and are easy to handle, but rarely used as alkylating agents in organic synthesis. Here, we describe a mild, straightforward and powerful method for nucleophilic alkylation of various N -, O -, C - and S -nucleophiles using readily available trialkyl phosphates. The reaction proceeds smoothly in excellent yield, and quantitative yield in many cases, and covers a wide range of substrates. Further, the rare stereoselective transfer of secondary alkyl groups has been achieved with inversion of configuration of chiral centers (up to 98% ee).

Nickel-Catalyzed Asymmetric Synthesis of α-Arylbenzamides

A nickel-catalyzed asymmetric reductive hydroarylation of vinyl amides to produce enantioenriched α-arylbenzamides is reported. The use of a chiral bisimidazoline (BIm) ligand, in combination with diethoxymethylsilane and aryl halides, enables the regioselective introduction of aryl groups to the internal position of the olefin, forging a new stereogenic center α to the N atom. The use of neutral reagents and mild reaction conditions provides simple access to pharmacologically relevant motifs present in anticancer, SARS-CoV PLpro inhibitors, and KCNQ channel openers.

Carboxyesterase polypeptides for amide coupling

The present invention provides engineered carboxyesterase enzymes having improved properties as compared to a naturally occurring wild-type carboxyesterase enzymes, as well as polynucleotides encoding the engineered carboxyesterase enzymes, host cells capable of expressing the engineered carboxyesterase enzymes, and methods of using the engineered carboxyesterase enzymes in amidation reactions.

Facile Synthesis of Chiral Arylamines, Alkylamines and Amides by Enantioselective NiH-Catalyzed Hydroamination

Regio- and enantioselective hydroarylamination, hydroalkylamination and hydroamidation of styrenes have been developed by NiH catalysis with a simple bioxazoline ligand under mild conditions. A wide range of enantioenriched benzylic arylamines, alkylamines and amides can be easily accessed by nitroarenes, hydroxylamines and dioxazolones, respectively as amination reagents. The chiral induction in these reactions is proposed to proceed through an enantiodifferentiating syn-hydronickellation step.

Fluorinated solvent-assisted photocatalytic aerobic oxidative amidation of alcoholsviavisible-light-mediated HKUST-1/Cs-POMoW catalysis

Considering the irreplaceable importance of photocatalytic functionalization reactions and the widespread attention paid to the use of metal-organic frameworks, especially their modified variants, for this purpose in recent years, different types of HKUST-1/POMoW composites were prepared through the immobilization of a series of Keggin-type polyoxometalates (POMs; POW = H3PW12O40, POMo = H3PMo12O40, and POMoW = H3PMo6W6O40) on HKUST-1 as a metal-organic framework (HKUST-1; Cu3(1,3,5-benzenetricarboxilicacid)2). Then, to produce HKUST-1/Cs-POM, the substitution of H+cations with Cs+ones as counter cations was carried out. The prepared composites were fully characterized with the PXRD (powder X-ray diffraction), FT-IR (Fourier transform infrared spectroscopy), BET and BJH (sorption of N2), TGA (thermo-gravimetric analysis), SEM (scanning electron microscopy), EDX (energy dispersive X-ray), TEM (transmission electron microscopy), UV-vis DRS (diffuse reflectance UV-vis spectroscopy), photoluminescence (PL) spectroscopy and ICP-AES (inductively coupled plasma atomic emission spectroscopy) techniques. The great importance?of the amide functional group and the attractiveness of photocatalytic oxidative functionalization?reactions led us to study the formation of this functional group using the prepared catalytic system in line with our previous research in this field. The HKUST-1/Cs-POMoW composite showed a raised photocatalytic performance compared to the discrete components, HKUST-1 and Cs-POMs, in aerobic oxidative amidation of alcohols under illumination with visible light, owing to the presence of catalytically active Cs-POMs deposited on the MOF particles. Besides, the combination of composite components mitigated the recombination rate of the electron-hole pairs, raising its photocatalytic activity. The attractiveness of fluorine solvents for oxidation reactions has led to the study of their role in the efficiency of oxidative amidation of alcohols and their significant effect on the efficiency of the process has been confirmed. The Cu-MOF/POM catalyst showed excellent stability during the reaction, and no significant decrease in its ability was observed during five consecutive cycles.