67907-59-9

Upstream product

• 67907-54-4 benzylidene-(3-chloro-benzyl)-amine 
• 141-52-6 sodium ethanolate 
• 587-04-2 m-Chlorobenzaldehyde 
• 100-46-9 benzylamine 

Downstream Products

• 67907-54-4 benzylidene-(3-chloro-benzyl)-amine 
• 501033-40-5 N-benzyl-1-(3-chlorophenyl)methanamine 
• 96788-21-5 Benzylamino-(3-chloro-phenyl)-acetonitrile 

Relevant academic research and scientific papers

Application of sequential Cu(I)/Pd(0)-catalysis to solution-phase parallel synthesis of combinatorial libraries of dihydroindeno[1,2-c]isoquinolines

Parallel solution-phase synthesis of combinatorial libraries of dihydroindenoisoquinolines employing a sequential Cu(I)/Pd(0)-catalyzed multicomponent coupling and annulation protocol was realized. The scope and limitations of the protocol with respect to the substitution pattern in the aryl ring of the indene core, as well as the N-substituent have been defined, revealing that the methodology is compatible with a wide-range of aliphatic linear, branched, and ester functionalized N-substituents. Unexpectedly, the formation of regioisomers featuring a 1,2,3-contiguous substitution pattern in the aromatic ring of the indene core was observed. Three distinct combinatorial libraries with a total of 111 of members were synthesized, and 80 highly substituted dihydroindenoisoquinolines structurally related to known medicinal agents including some consisting of mixtures of two regioisomers were made available for biological activity testing.

Allosteric functional switch of neurokinin A-mediated signaling at the neurokinin NK2 receptor: Structural exploration

The neurokinin NK2 receptor is known to pre-exist in equilibrium between at least three states: restinginactive, calcium-triggering, and cAMP-producing. Its endogeneous ligand, NKA, mainly induces the calcium response. Using a FRET-based assay, we have previously discovered an allosteric modulator of the NK2 receptor that has the unique ability to discriminate among the two signaling pathways: calcium-signaling is not affected while cAMP signaling is significantly decreased. A series of compounds have been prepared and studied in order to better understand the structural determinants of this allosteric functional switch of a GPCR. Most of them display the same allosteric profile, with smooth pharmacomodulation. One compound however exhibits significantly improved modulatory properties of NKA induced signaling when compared to the original modulator. 2009 American Chemical Society.

Catalytic, asymmetric Strecker reactions catalysed by titaniumIV and vanadiumV(salen) complexes

VanadiumV(salen) complex 3 has been found to be an effective catalyst for the asymmetric addition of hydrogen cyanide (generated in situ from trimethylsilyl cyanide) to imines. The best results (up to 81% enantiomeric excess) were obtained for aromatic imines in which the nitrogen atom is protected with a benzyl group and in which the imine bond is not sterically encumbered.

Oxidative N-debenzylation of N-benzyl-N-substituted benzylamines catalyzed by horseradish peroxidase

A report on the oxidative N-debenzylation of N-benyl-N-substituted benzylamines catalyzed by horseradish peroxidase was presented. A solution of benzylamine in benzene was added to a benzene solution of p-anisaldehyde in 100 ml flask over 10 minutes. Expulsion of proton and hydroxylation yielding α-hydroxylamines were followed by the formation of benzaldehydes and benzylamines.

C-H and C-Cl bond activation in the formation of cyclometallated platinumt(II) and platinum(IV) compounds with chlorinated N-benzylidenebenzylamines

Platinum substrate [Pt2Me4(μ-SMe2)2] (1) reacts with chlorinated imines 3,5-Cl2C6H3CH=NCH2C6H5 (2a) and 3-ClC6H4CH=NCH2C6H5 (2b) to yield cyclometallated platinum(II) compounds [PtMe(3,5-Cl2C6H2CH=NCH2C5H5)(SMe2)] (4a) and [PtMe(3-ClC6H3CH=NCH2C6H5)(SMe2)] (4b), arising from C-H bond activation followed by loss of methane. A reaction intermediate [PtMe2(3,5-Cl2C6H3CH=NCH2C6H5)(SMe2)] (3a) was detected by 1H NMR. The reaction of [Pt2Me4(μ-SMe2)2] (1) with chlorinated imine 2,4-Cl2C6H3CH=NCH2C6H5 (2c) produces a mixture of cyclometallated platinum(II) compound [PtMe(2,4-Cl2C6H2CH=NCH2C6H5)(SMe2)] (4c) and cyclometallated platinum(IV) compound [PtMe2Cl(4-ClC6H3CH=NCH2C6H5)(SMe2)] (4c′) arising respectively from aryl C-H and aryl C-Cl bond activation. The reaction of complex 4a with triphenylphosphine produces metallacycle cleavage and [PtMe(3,5-Cl2C6H2CH=NCH2C6H5)(PPh3)2] (5a) is formed with the imine acting as a [C-] unidentate ligand. 5a crystallizes in the monoclinic space group P21/n with a = 10.899(5) A, b = 22.953(5) A and c = 17.588(9) A, β = 95.14(5)° and Z = 4. Compounds 4b, 4c and 4c′ react with PPh3 to give cyclometallated compounds [PtMe(3-ClC6H3CH=NCH2C6H5)(PPh3)] (5b), [PtMe(2,4-Cl2C6H2CH=NCH2C6H5)(PPh3)] (5c), and [PtMe2Cl(4-ClC6H3CH=NCH2C6H5)(PPh3)] (5c′) respectively. The stereo-electronic effect of chlorine substituents, as well as the NMR parameters, are discussed in relation to the observed reactivity of these compounds.