79328-85-1

Basic information

• Product Name: BENZYL PYRIDINE-1(2H)-CARBOXYLATE
• Synonyms: BENZYL PYRIDINE-1(2H)-CARBOXYLATE
• CAS NO: 79328-85-1
• Molecular Formula: C₁₃H₁₃NO₂
• Molecular Weight: 215.24782
• Mol File: 79328-85-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: BENZYL PYRIDINE-1(2H)-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL PYRIDINE-1(2H)-CARBOXYLATE(79328-85-1)
• EPA Substance Registry System: BENZYL PYRIDINE-1(2H)-CARBOXYLATE(79328-85-1)

Safety Data

• Hazardous Substances Data: 79328-85-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Syntheses:
BENZYL PYRIDINE-1(2H)-CARBOXYLATE is used as a chemical intermediate for the synthesis of various compounds. Its reactive ester group allows it to participate in a range of chemical reactions, making it a valuable component in the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Industrial Applications:
BENZYL PYRIDINE-1(2H)-CARBOXYLATE is used as a raw material in the manufacturing of various industrial products. Its aromatic structure and ester functionality contribute to the development of new materials with specific properties, such as fragrances, dyes, and coatings.
Used in Pharmaceutical Industry:
BENZYL PYRIDINE-1(2H)-CARBOXYLATE is used as a building block in the development of new drugs. Its unique structure may provide novel pharmacological properties, making it a potential candidate for the treatment of various diseases and medical conditions.
Used in Agrochemical Industry:
BENZYL PYRIDINE-1(2H)-CARBOXYLATE is used as a component in the formulation of agrochemicals, such as pesticides and herbicides. Its chemical properties may contribute to the effectiveness of these products in controlling pests and weeds in agricultural settings.

Upstream product

• 110-86-1 pyridine 
• 501-53-1 benzyl chloroformate 
• 89129-21-5 N-benzyloxycarbonyl-7-chloro-7-methoxycarbonyl-2-azabicyclo[2.2.2]oct-5-ene 
• 920-37-6 2-Chloroacrylonitrile 

Downstream Products

• 128826-70-0 (+/-)-3-(Benzyloxycarbonyl)-7-chloro-3-azabicyclo<4.2.0>oct-4-ene-7-carboxylic Acid Methyl Ester 
• 89129-21-5 (+/-)-2-(Benzyloxycarbonyl)-7-exo-chloro-2-azabicyclo<2.2.2>oct-5-ene-7-endo-carboxylic Acid Methyl Ester 
• 89129-21-5 (+/-)-2-(Benzyloxycarbonyl)-7-endo-chloro-2-azabicyclo<2.2.2>oct-5-ene-7-exo-carboxylic Acid Methyl Ester 
• 89129-21-5 N-benzyloxycarbonyl-7-chloro-7-methoxycarbonyl-2-azabicyclo[2.2.2]oct-5-ene 
• 130114-74-8 (4aS,8aR)-3-Phenyl-8,8a-dihydro-4aH-pyrido[4,3-e][1,4,2]dioxazine-7-carboxylic acid benzyl ester 
• 79328-88-4 methyl 2-(benzyloxycarbonyl)-7-exo-(1-phenylsulfonylindol-2-yl)-2-azabicyclo[2.2.2]oct-5-ene-7-endo-carboxylate 
• 13407-35-7 (2R,3R,4S,5S)-2,3,4,5-Tetrahydroxy-piperidine-1-carboxylic acid benzyl ester 
• 157425-56-4 2,3-Dioxa-5-aza-bicyclo[2.2.2]oct-7-ene-5-carboxylic acid benzyl ester 
• 104704-55-4 2-benzyloxycarbonyl-2-azabicyclo<2.2.0>hexa-5-ene 
• 114704-07-3 2-benzyl 7-methyl 2-azbicyclo[2.2.2]oct-5-ene-2,7-dicarboxylate 
• 114704-07-3 2-benzyl 7-methyl 2-azbicyclo[2.2.2]oct-5-ene-2,7-dicarboxylate 
• 189184-88-1 (1R,4R,7R)-7-((1S,2R,6S,7R)-7,10,10-Trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-en-4-yl)-2-aza-bicyclo[2.2.2]oct-5-ene-2-carboxylic acid benzyl ester 
• 104-57-4 benzyl formate 
• 120-51-4 benzoic acid benzyl ester 

Relevant articles and documents

Synthesis of isoquinuclidine analogs of chloroquine: Antimalarial and antileishmanial activity

The isoquinuclidine (2-azabicyclo[2.2.2]octane) ring system may be viewed as a semi-rigid boat form of the piperidine ring and, when properly substituted, a scaffold for rigid analogs of biologically active ethanolamines and propanolamines. It is present in natural products (such as ibogaine and dioscorine) that display interesting pharmacological properties. In this study, we have expanded our continuing efforts to incorporate this ring system in numerous pharmacophores, by designing and synthesizing semirigid analogs of the antimalarial drug chloroquine. The analogs were tested in vitro against Plasmodium falciparum strains and Leishmania donovani promastigote cultures. Compounds 6 and 13 displayed potent antimalarial activity against both chloroquine-susceptible D6 and the -resistant W2 strains of P. falciparum. All analogs also demonstrated significant antileishmanial activity with compounds 6 and 13 again being the most potent. The fact that these compounds are active against both chloroquine-resistant and chloroquine-sensitive strains as well as leishmanial cells makes them promising candidates for drug development.

A non-hallucinogenic psychedelic analogue with therapeutic potential

The psychedelic alkaloid ibogaine has anti-addictive properties in both humans and animals1. Unlike most medications for the treatment of substance use disorders, anecdotal reports suggest that ibogaine has the potential to treat addiction to v

Enantioselective Formal Total Synthesis of (-)-Quinagolide

The enantioselective formal total synthesis of (-)-quinagolide has been accomplished in a linear sequence of 8 purification steps from pyridine. The key steps are (a) organocatalyzed Diels-Alder reaction for fixing all three stereocenters on piperidine ri

Clathrodin, hymenidin and oroidin, and their synthetic analogues as inhibitors of the voltage-gated potassium channels

We have prepared three alkaloids from the Agelas sponges, clathrodin, hymenidin and oroidin, and a series of their synthetic analogues, and evaluated their inhibitory effect against six isoforms of the Kv1 subfamily of voltage-gated potassium channels, Kv1.1-Kv1.6, expressed in Chinese Hamster ovary (CHO) cells using automated patch clamp electrophysiology assay. The most potent inhibitor was the (E)-N-(3-(2-amino-1H-imidazol-4-yl)allyl)-4,5-dichloro-1H-pyrrole-2-carboxamide (6g) with IC50 values between 1.4 and 6.1 μM against Kv1.3, Kv1.4, Kv1.5 and Kv1.6 channels. All compounds tested displayed selectivity against Kv1.1 and Kv1.2 channels. For confirmation of their activity and selectivity, compounds were additionally evaluated in the second independent system against Kv1.1-Kv1.6 and Kv10.1 channels expressed in Xenopus laevis oocytes under voltage clamp conditions where IC50 values against Kv1.3-Kv1.6 channels for the most active analogues (e.g. 6g) were lower than 1 μM. Because of the observed low sub-micromolar IC50 values and fairly low molecular weights, the prepared compounds represent good starting points for further optimisation towards more potent and selective voltage-gated potassium channel inhibitors.

Diels-Alder Reactions of α-Amido Acrylates with N-Cbz-1,2-dihydropyridine and Cyclopentadiene

Thermal Diels-Alder reactions of α-amido acrylates with N-Cbz-1,2-dihydropyridine and cyclopentadiene have been explored to investigate the factors influencing the endo/exo selectivity. For the dihydropyridine, steric factors allowed the diastereoselectivity to be modulated to favor either endo- or exo-ester adducts. For cyclopentadiene, the endo-ester adducts were favored regardless of steric perturbation, although catalysis by bulky Lewis acids increased the proportion of exo-ester adducts in some cases. These Lewis acids were incompatible with the dihydropyridine diene as they induced its decomposition.

Pathogen detection

Pathogens are detected through the use of mutation-resistant ligands.

Enantioselective Synthesis of Chiral Piperidines via the Stepwise Dearomatization/Borylation of Pyridines

We have developed a novel approach for the synthesis of enantioenriched 3-boryl-tetrahydropyridines via the Cu(I)-catalyzed regio-, diastereo-, and enantioselective protoborylation of 1,2-dihydropyridines, which were obtained by the partial reduction of the pyridine derivatives. This dearomatization/enantioselective borylation stepwise strategy provides facile access to chiral piperidines together with the stereospecific transformation of a stereogenic C-B bond from readily available starting materials. Furthermore, the utility of this method is demonstrated for the concise synthesis of the antidepressant drug (-)-paroxetine. A theoretical study of the reaction mechanism is also described.

A convenient strategy for synthesizing the Agelas alkaloids clathrodin, oroidin, and hymenidin and their (un)saturated linker analogs

A convenient strategy for the scalable synthesis of the 2-aminoimidazole alkaloids, clathrodin, oroidin, and hymenidin derived from marine Agelas species and their analogs possessing a saturated or unsaturated linker moiety is described. The key intermediates, 4-(3-aminopropyl)-1H-imidazol-2-amine and (E)-4-(3-aminoprop-1-en-1-yl)-1H-imidazol-2-amine were obtained through two different synthetic pathways starting from l-ornithine and benzyl 1,2-dihydropyridine-1-carboxylate respectively, using (i) an innovative combination of Weinreb amide strategy with di-Boc protection, and (ii) a modified pyridine-1(2H)-carboxylate based strategy. Convenient access to these 2-aminoimidazole amines is crucial for the synthesis of libraries of clathrodin, oroidin, and hymenidin analogs.

Highly enantioselective synthesis of isoquinuclidine by diels-alder reaction of 1,2-dihydropyridine utilizing chiral bisoxazoline-Cu(II) complex

The enantioselective Diels-Alder (D-A) reaction between N-phenoxycarbonyl- or N-benzyloxycarbonyl-1,2-dihydropyridine (1a or 1b) and N(2)-acryloyl-N(1)-(1- naphthylmethyl)-5,5-dimethylpyrazolidin-3-one (2b) using (S,S)-bisoxazoline- Cu(II) catalyst (A, B, C or D) has been investigated. Utilizing (S,S)-t-Bu-bisoxazoline-Cu(II) catalyst C, the D-A reaction of 1a and 2 afforded the endo-(7S)-isoquinuclidines (3, 4 or 5) in good chemical yields with high enantioselectivity (up to 99% e.e.).

Reductive Heck coupling: An efficient approach toward the iboga alkaloids. Synthesis of ibogamine, epiibogamine and iboga analogs

A mild and efficient synthetic route to the iboga scaffold by employing reductive-Heck type annulation is described. The utility of this process is demonstrated by the direct access to the ibogamine, epiibogamine and iboga-analogs. The cyclization precursors were readily obtained from 2-iodoaniline by heteroannulation reaction with suitable alkynes followed by iodination.