66207-23-6

Basic information

• Product Name: N-CBZ-1,2,3,6-TETRAHYDROPYRIDINE
• Synonyms: N-CBZ-1,2,3,6-TETRAHYDROPYRIDINE;N-CBZ-1,2,5,6-TETRAHYDROPYRIDINE;benzyl 5,6-dihydropyridine-1(2H)-carboxylate;1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridine;benzyl 1,2,3,6-tetrahydropyridine-1-carboxylate;benzyl 3,6-dihydro-2H-pyridine-1-carboxylate;1(2H)-Pyridinecarboxylic acid, 3,6-dihydro-, phenylmethyl ester;benzyl 3,6-dihydropyridine-1(2H)-carboxylate
• CAS NO: 66207-23-6
• Molecular Formula: C₁₃H₁₅NO₂
• Molecular Weight: 217.26
• Product Categories: Heterocycle-Pyridine series
• Mol File: 66207-23-6.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 334.606°C at 760 mmHg
• Flash Point: 156.164°C
• Appearance: /
• Density: 1.149g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.566
• Storage Temp.: 2-8°C
• PKA: -1.46±0.20(Predicted)
• CAS DataBase Reference: N-CBZ-1,2,3,6-TETRAHYDROPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-CBZ-1,2,3,6-TETRAHYDROPYRIDINE(66207-23-6)
• EPA Substance Registry System: N-CBZ-1,2,3,6-TETRAHYDROPYRIDINE(66207-23-6)

Safety Data

• Hazardous Substances Data: 66207-23-6(Hazardous Substances Data)

Usage

Uses

3,6-Dihydro-1(2H)-pyridinecarboxylic Acid Phenylmethyl Ester is used in the synthesis of potent antibacterials targeting type IIA topoisomerases. Also used in the synthesis of inhibitors of papain-like cathespin proteases.

InChI:InChI=1/C13H15NO2/c15-13(14-9-5-2-6-10-14)16-11-12-7-3-1-4-8-12/h1-5,7-8H,6,9-11H2

Upstream product

• 694-05-3 1,2,3,6-tetrahydropyridine 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 13291-18-4 isopropenylmagnesium bromide 
• 166953-64-6 benzyl 4-bromo-1-piperidinecarboxylate 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 
• 885275-00-3 4-iodo-piperidine-1-carboxylic acid benzyl ester 
• 100-42-5 styrene 
• 95798-22-4 3-hydroxy-piperidine-1-carboxylic acid benzyl ester 
• 501-53-1 benzyl chloroformate 
• 95798-23-5 1-(benzyloxycarbonyl)-4-hydroxypiperidine 
• 169750-63-4 benzyl 3-[(methylsulfonyl)oxy]piperidine-1-carboxylate 
• 507-09-5 tiolacetic acid 
• 199103-19-0 benzyl 4-[(methylsulfonyl)oxy]piperidine-1-carboxylate 
• 5382-16-1 4-HYDROXYPIPERIDINE 

Downstream Products

• 167096-99-3 (+/-)-cis-1-benzyloxycarbonyl-3,4-dihydroxypiperidine 
• 266688-41-9 (3R,4R)-(+)-trans-1-benzyloxycarbonyl-3,4-dihydroxypiperidine 
• 1624258-63-4 rac-benzyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate 
• 167096-99-3 (3S,4S)-1-benzyloxycarbonyl-3,4-dihydroxypiperidine 
• 1624258-63-4 (1S,6R)-7-oxa-3-aza-bicyclo[4.1.0]heptane-3-carboxylic acid benzyl ester 
• 905281-83-6 benzyl 4-(4-bromo-3-(pyridin-4-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate 
• 1523541-91-4 (4-hydroxypiperidin-3-yl)carbamic acid tert-butyl ester 
• 167096-99-3 3,4-dihydroxypiperidine-1-carboxylic acid benzyl ester 
• 1247884-87-2 3,4-diazidopiperidine-1-carboxylic acid benzyl ester 
• 1247884-89-4 benzyl 3,4-diaminopiperidine-1-carboxylate 
• 203503-29-1 4-azido-3-hydroxypiperidine-1-carboxylic acid benzyl ester 
• 1174063-42-3 3-azido-4-hydroxypiperidine-1-carboxylic acid benzyl ester 

Relevant articles and documents

Cobalt-Catalyzed C(sp2)-C(sp3) Suzuki-Miyaura Cross Coupling

A cobalt-catalyzed method for the C(sp2)-C(sp3) Suzuki-Miyaura cross coupling of aryl boronic esters and alkyl bromides is described. Cobalt-ligand combinations were assayed with high-throughput experimentation, and cobalt(II) sources with trans-N,N′-dimethylcyclohexane-1,2-diamine (DMCyDA, L1) produced optimal yield and selectivity. The scope of this transformation encompassed steric and electronic diversity on the aryl boronate nucleophile as well as various levels of branching and synthetically valuable functionality on the electrophile. Radical trap experiments support the formation of electrophile-derived radicals during catalysis.

Method for preparing N-substituted-1,2,3,6-tetrahydropyridine

The invention discloses a method for preparing N-substituted-1,2,3,6-tetrahydropyridine and belongs to the technical field of organic chemistry. N-substituted-4-piperidinol as a raw material reacts with triphenylphosphine and azodicarbonic acid diester, alcoholic hydroxyl groups are converted into alkenyl groups, and N-substituted-1,2,3,6-tetrahydropyridine is prepared. The method has the advantages that the raw materials are easily available, the operation is simple and convenient, the product purity is high, demands of the conventional method for high-temperature condition and highly toxic chemicals are avoided, and the method has potential route advantage.

Activity-Directed Synthesis with Intermolecular Reactions: Development of a Fragment into a Range of Androgen Receptor Agonists

Activity-directed synthesis (ADS), a novel discovery approach in which bioactive molecules emerge in parallel with associated syntheses, was exploited to develop a weakly binding fragment into novel androgen receptor agonists. Harnessing promiscuous intermolecular reactions of carbenoid compounds enabled highly efficient exploration of chemical space. Four substrates were prepared, yet exploited in 326 reactions to explore diverse chemical space; guided by bioactivity alone, the products of just nine of the reactions were purified to reveal diverse novel agonists with up to 125-fold improved activity. Remarkably, one agonist stemmed from a novel enantioselective transformation; this is the first time that an asymmetric reaction has been discovered solely on the basis of the biological activity of the product. It was shown that ADS is a significant addition to the lead generation toolkit, enabling the efficient and rapid discovery of novel, yet synthetically accessible, bioactive chemotypes.