115397-88-1

Upstream product

• 74083-63-9 (E)-N-(3-methoxybenzylidene)-1-phenylmethanamine 
• 141-52-6 sodium ethanolate 
• 5071-96-5 3-METHOXYBENZYLAMINE 
• 100-52-7 benzaldehyde 
• 38489-80-4 3-methoxybenzaldehyde oxime 
• 591-31-1 3-methoxy-benzaldehyde 
• 100-46-9 benzylamine 
• 2835-06-5 phenylglycin 
• 1527-89-5 3-methoxybenzonitrile 

Downstream Products

• 74083-63-9 (E)-N-(3-methoxybenzylidene)-1-phenylmethanamine 

Relevant academic research and scientific papers

Novel transition bimetal-organic frameworks: Recyclable catalyst for the oxidative coupling of primary amines to imines at mild conditions

A novel type of transition bimetal-organic frameworks was described as a heterogeneous catalyst for the oxidative coupling of amines to imines under mild conditions, which was easily synthesized by the coordination assembly of manganese(ii) and cobalt(ii) with 1,3,5-benzenetricarboxylic acid (H3BTC) for the first time. The metal-organic framework material was characterized by scanning electron microscopy, energy dispersive spectroscopy, X-ray photoelectron spectroscopy, X-ray diffraction, thermogravimetry and N2 sorption. As an environmentally benign heterogeneous catalyst, the catalytic ability of the metal-organic framework material was then detected to be excellent for the tert-butyl hydroperoxide (TBHP) promoted direct oxidative coupling of benzylamines to imines in excellent yields (up to 100%) in methanol for 3 h. More importantly, it could be recycled up to six runs, while still maintaining its high catalytic activity.

Efficient Co-Catalyzed Double Hydroboration of Nitriles: Application to One-Pot Conversion of Nitriles to Aldimines

The commercially available and bench-stable Co(acac)2/dpephos system is employed as a precatalyst for selective and efficient room temperature hydroboration of organic nitriles with HBPin to produce a series of N,N-diborylamines [RN(BPin)2], which react in situ with aldehydes to give aldimines. Formation of aldimines from N,N-diborylamines does not require a dehydrating agent, is applicable to a wide range of N,N-diborylamine and aldehyde substrates and is highly chemoselective, being unaffected by various common functional groups, such as alkenes, alkynes, secondary amines, ketones, esters, amides, carboxylic acids, pyridines, nitriles, and nitro compounds. The overall transformation represents a synthetically valuable approach to aldimines from nitriles and can be performed in a sequential one-pot manner, tolerating ester, lactone, carboxamide and unactivated alkene functionalities.

Ligand-Controlled Inversion of Diastereo- and Enantioselectivity in Silver-Catalyzed Azomethine Ylide-Imine Cycloaddition of Glycine Aldimino Esters with Imines

A highly diastereo- and enantioselective silver-catalyzed azomethine ylide-imine (AYI) cycloaddition reaction of glycine aldimino esters with imines was developed in which the Xing-Phos-controlled syn-selective or DTBM-Segphos-induced anti-selective AYI cycloaddition reaction could be applied to the synthesis of a variety of stereodivergent 1-alkyl-2,5-substituted imidazolidines with high yields and excellent enantioselectivities (up to 99% ee) as well as good diastereoselectivities (up to 99:1 dr) under mild reaction conditions.

Homologation of α-aryl amino acids through quinone-catalyzed decarboxylation/Mukaiyama-Mannich addition

A new method for amino acid homologation by way of formal C-C bond functionalization is reported. This method utilizes a 2-step/1-pot protocol to convert α-amino acids to their corresponding N-protected β-amino esters through quinone-catalyzed oxidative decarboxylation/in situ Mukaiyama-Mannich addition. The scope and limitations of this chemistry are presented. This methodology provides an alternative to the classical Arndt-Eistert homologation for accessing β-amino acid derivatives. The resulting N-protected amine products can be easily deprotected to afford the corresponding free amines.

Selective extraction of N2 from air by diarylimine iron complexes

Treatment of cis-(Me3P)4FeMe2 with ortho-substituted diarylimines afforded 2 equiv of MeH, PMe3, and {mer-κC,N,C′-(Ar-2-yl)CH2N=CH(Ar′-2-yl)}Fe(PMe 3)3 (Ar = 3,4,6-(F)3-C6H, Ar′ = 3,5-(CF3)2-C6H2, 1a; Ar = 3,4,6-(F)3-C6H, Ar′ = 3,4,5-(F)3-C 6H, 1b; Ar = 4,5,6-(F)3-C6H, Ar′ = 3,5-(CF3)2-C6H2, 1c; Ar = C 6H4, Ar′ = 3-(OMe)-C6H3, 1d; Ar = 4,5,6-(F)3-C6H, Ar′ = 3,6-Me2-C 6H3, 1e; Ar = C6H4, Ar′ = 3,6-Me2-C6H2, 1f). Exposure of 1a-f to O 2 caused rapid degradation, but substitution of the unique PMe 3 with N2 occurred when 1a-f were exposed to air or N 2 (1 atm), yielding {mer-κC,N,C′-(Ar-2-yl)CH 2N=CH(Ar′-2-yl)}Fe(PMe3)2L (L = N 2, 2a-f); CO, CNMe, and N2CPh2 derivatives (L = CO, 3a-d,f; L = CNMe, 8b; L = N2CPh2, 9b) were prepared. Dihydrogen or NH3 binding to {mer-κC,N,C′-(3,4,6-(F) 3-C6H-2-yl)CH2N=CH-(3,4,5-(F) 3-C6H-2-yl)}Fe(PMe3)2 (1b′, S = 1 (calc)) to provide 5b (L = H2) or 6b (L = NH3) was found comparable to that of N2, while PMe3 (1b) and pyridine (L = py, 7b) adducts were unfavorable. Protolytic conditions were modeled using HCCR as weak acids, and trans-{κC,N-(3,4,5-(F) 3-C6H2)CH2N=CH(3,4,6-(F) 3-C6H-2-yl)}Fe(PMe3)3(CCR) (R = Me, 4b-Me; R = Ph, 4b-Ph) were generated from 1b. Exposure of 1b to N2O or N3SO2tol generated 2b and Me3PO or Me 3P=N(SO2)tol, respectively. Calculations revealed 2b to be thermodynamically and kinetically favored over the calculated Fe(III) superoxide complex, 3[FeO2], relative to 1b′ + N2 + O2. The correlation of 1b′ + 3O 2 to 3[FeO2] is likely to have a relatively high intersystem crossing point (ICP) relative to 1b′ + N2 to 2b, thereby explaining the dinitrogen selectivity.

Phosphatase inhibitors. III. Benzylaminophosphonic acids as potent inhibitors of human prostatic acid phosphatase

Further investigation of the structural requirements of a series of benzylphosphonic acid inhibitors of human prostatic acid phosphatase has led to the highly potent series of α-aminobenzylphosphonic acids. The α-benzylaminobenzylphosphonic acid, with an IC50 = 4 nM, exhibited a 3500-fold improvement in potency over the carbon analogue, α-phenylethyl. The enhanced potency may be due to a combination of four favorable interactions including those with the phosphate binding region, the presence the hydrophobic moieties of the benzylamino and phenylphosphonic acid, and a rigid conformer produced by an internal salt bridge between the phosphonate and the α-amino group. Replacement of the phosphonic acid moiety with a phosphinic or carboxylic acid as well as deletion of the benzyl substitution on the α-amino group led to great reductions in potency.