5433-11-4

Upstream product

• 100-52-7 benzaldehyde 
• 156-87-6 propan-1-ol-3-amine 

Downstream Products

• 174311-02-5 2-phenylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 174310-75-9 2-phenylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 98014-77-8 3-(N-benzyl-N-tert-butoxycarbonylamino)propanal 
• 105427-51-8 C₆H₅CHNCH₂CH₂CH₂OCH₃ 
• 1021461-29-9 [Pd(C6H4-2-C(H)=NCH2CH2CH2OH-κ-C1,N)(triphenylphosphine)][triflate] 
• 1021461-23-3 [PdCl(C6H4-2-C(H)=NCH2CH2CH2OH-κ-C1,N)(triphenylphosphine)] 
• 23956-46-9 3-(3-dimethylamino-propyl)-2-phenyl-2,3-dihydro-benzo[e][1,3]thiazin-4-one 
• 17785-45-4 3-(3-chloro-propyl)-2-phenyl-2,3-dihydro-benzo[e][1,3]thiazin-4-one 
• 88690-79-3 3-(4-Nitrobenzoyloxy)-2-(4-nitrophenyl)-perhydro-1,3-oxazin 
• 88690-81-7 2-(4-Chlorphenyl)-3-(4-nitrobenzoyloxy)-perhydro-1,3-oxazin 

Relevant academic research and scientific papers

[Co(TPP)]-Catalyzed Formation of Substituted Piperidines

Radical cyclization via cobalt(III)-carbene radical intermediates is a powerful method for the synthesis of (hetero)cyclic structures. Building on the recently reported synthesis of five-membered N-heterocyclic pyrrolidines catalyzed by CoII porphyrins, the [Co(TPP)]-catalyzed formation of useful six-membered N-heterocyclic piperidines directly from linear aldehydes is presented herein. The piperidines were obtained in overall high yields, with linear alkenes being formed as side products in small amounts. A DFT study was performed to gain a deeper mechanistic understanding of the cobalt(II)-porphyrin-catalyzed formation of pyrrolidines, piperidines, and linear alkenes. The calculations showed that the alkenes are unlikely to be formed through an expected 1,2-hydrogen-atom transfer to the carbene carbon. Instead, the calculations were consistent with a pathway involving benzyl-radical formation followed by radical-rebound ring closure to form the piperidines. Competitive 1,5-hydrogen-atom transfer from the β-position to the benzyl radical explained the formation of linear alkenes as side products.

Preparation method of 8-tert-butyl-1-ethyl-6,7-dihydro-5H-imidazo[1,5-a][1,4]diazepine-1,8(9H)-dicarboxylic acid ester

The invention relates to a preparation method of 8-tert-butyl-1-ethyl-6,7-dihydro-5H-imidazo[1,5-a][1,4]diazepine-1,8(9H)-dicarboxylic acid ester. A purpose of the present invention is to mainly solvethe technical problem that no suitable industrial synthesis method exists at present. According to the present invention, the method comprises nine steps, the synthetic route is defined in the specification, and the obtained compound can be used as the useful intermediate or product for synthesizing a plurality of medicines.

Enantioselective Radical Cyclization for Construction of 5-Membered Ring Structures by Metalloradical C-H Alkylation

Radical cyclization represents a powerful strategy for construction of ring structures. Traditional radical cyclization, which is based on radical addition as the key step, necessitates the use of unsaturated substrates. Guided by the concept of metalloradical catalysis, a different mode of radical cyclization that can employ saturated C-H substrates is demonstrated through the development of a Co(II)-based system for catalytic activation of aliphatic diazo compounds for enantioselective radical alkylation of various C(sp3)-H bonds. It allows for efficient construction of chiral pyrrolidines and other valuable 5-membered cyclic compounds. This alternative strategy of radical cyclization provides a new retrosynthetic paradigm to prepare five-membered cyclic molecules from readily available open-chain aldehydes through the union of C-H and C=O elements for C-C bond formation.

Manganese catalyzed reductive amination of aldehydes using hydrogen as a reductant

A one-pot two-step procedure was developed for the alkylation of amines via reductive amination of aldehydes using molecular dihydrogen as a reductant in the presence of a manganese pyridinyl-phosphine complex as a pre-catalyst. After the initial condensation step, the reduction of imines formed in situ is performed under mild conditions (50-100 °C) with 2 mol% of catalyst and 5 mol% of tBuOK under 50 bar of hydrogen. Excellent yields (>90%) were obtained for a large combination of aldehydes and amines (40 examples), including aliphatic aldehydes and amino-alcohols.

Method for preparing amino ether compounds

The invention belongs to the technical field of organic synthesis and relates to a method for preparing amino ether compounds. The method comprises the following steps: by taking amino alcohol as a raw material, protecting amino in the amino alcohol so as to obtain Schiff base; carrying out an etherification reaction on the hydroxyl group in the Schiff base; and finally, performing amino deprotection, thereby obtaining corresponding amino ethers. The method disclosed by the invention has high regio-selectivity, the substrates of higher than 99.9% are subjected to etherification reaction, the reaction conversion ratio of each step is higher than 99.8%, and the total yield is higher than 95%; when amino alcohol is chiral, the amino ethers with retention of configuration can be obtained; and moreover, each step of the method is a conventional operation, the process cost is low, and three wastes are few, the energy consumption is low, an environment-friendly effect is achieved, and large-scale industrial production is easily realized.

Two stepwise synthetic routes toward a hetero[4]rotaxane

Heterorotaxanes have been emerging as an important class of mechanically interlocked molecules and have attracted much attention in recent years. Driven by the distinguishable host-guest interactions between crown ether macrocycles and ammonium with different sizes, a novel hetero[4]rotaxane was successfully prepared by employing the combination of copper-catalyzed "click" reaction and P(n-Bu)3-catalyzed esterification reaction as stoppering reactions. The hetero[4]rotaxane contains an interlocked species in which a dibenzo[24]crown-8 ring threaded by a dibenzylammonium-containing component with two benzo[21]crown-7 macrocycles at both ends to act as stoppers, and each of the two benzo[21]crown-7 rings is also threaded with a benzylalkylammonium unit to form the second interlocked species. The hetero[4]rotaxane was prepared through two different stepwise synthetic routes, and the complicated chemical structure of the hetero[4]rotaxane was well-characterized by 1H NMR spectroscopy and high-resolution electrospray ionization (HR-ESI) mass spectrometry. The investigation shows that the construction of complicated topological heterorotaxane can be achieved via distinct approaches with high efficiencies, which may provide a foundation for the construction of more sophisticated heterorotaxane systems or functional supermolecules.

Synthesis of noncyclic carriers for cerium ion transport through polymer inclusion membrane

Noncyclic ionophores having both diphenylphosphinyl methylcarbamoyl and N,N-di(2-ethylhexyl)carbamoylmethoxy groups were synthesized for cerium ion transport through polymer inclusion membrane. The derivative of 3-aminopropanol having these groups was fou

Bite angle effect of bidentate P-N ligands in palladium catalysed allylic alkylationf

Two series of new bidentate P-N ligands have been synthesized. Application of these ligands in the palladium catalysed allylic alkylation of crotyl chloride and cinnamyl chloride leads to the preferential formation of the branched product. A larger bite angle of the ligand leads to higher regioselectivity. Stoichiometric alkylation of the complex [Pd(C4H7){p-MeOC6H4C=N(CH 2)4OPPh2}][O3SCF3] proceeds with 88% regioselectivity to the branched product. The Royal Society of Chemistry 2000.

New anti-HIV derivatives: Synthesis and antiviral evaluation

A small focused library of 18 compounds incorporating the motif 1,3-(N,N'-dibenzyl)diamino-2-propanol has been synthesized, using adapted synthetic methodologies. These series of compounds were evaluated for their in vitro anti-HIV activity on infected MT4 cells (syncytium formation observation). Some of the new synthesized compounds show potent anti-HIV activities. EC50 values for compounds (31, 40, 34, 37 and 46Scheme 3(i) Na2SO4, CH2Cl2, rt; (ii) NaBH4, EtOH, 0°C; (iii) Boc2O, CH2Cl2, 0°C; (iv) DMSO, TFAA, Et3N, CH2Cl2, -60°C; (v) TFA, CH2Cl2, rt; (vi) BOP, RCOOH, Et3N, CH2Cl2, rt.) range from 0.1 to 1μM. In order to determine at which level these new derivatives interfere with the HIV replicative cycle, inhibition assays on recombinant HIV protease and HIV integrase have been performed. None of the compounds were found active on these two enzymatic targets. Experiments are in progress in order to identify their biological target within the HIV replicative cycle. Copyright (C) 2000 Elsevier Science Ltd.

1,3-Dipolar Cycloaddition of Imidate Ylides on Imino-Alcohols: Synthesis of New Imidazolones Using Solvent Free Conditions.

Imidates derived from α-amino esters as potential azomethine ylides, undergo 1,3-dipolar cycloaddition with imino-alcohols, in tautomeric equilibrium with 1,3-oxazolidines, without solvent at 70 deg C or under microwave irradiation.This reaction leads to a wide range of novel polyfunctionalized 4-yliden-2-imidazolin-5-ones in good yields with short reaction times.The reactivity of these imidates derived from α-amino esters with imino-alcohols is rationalized from the energy of the Frontier Molecular Orbitals (FMO) determined by semi-empirical PM3 calculations : the reaction is controlled by the interaction HOMO(1,3-dipole) - LUMO(dipolarophile) and the second order perturbation energy calculations are in agreement with the experimental reaction orientation.