206446-47-1

Basic information

• Product Name: 1-Boc-4-(2-propen-1-yl)-piperidine
• Synonyms: 1-Boc-4-(2-propen-1-yl)-piperidine
• CAS NO: 206446-47-1
• Molecular Formula: C₁₃H₂₃NO₂
• Molecular Weight: 225.33
• Product Categories: pharmacetical
• Mol File: 206446-47-1.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 287.708°C at 760 mmHg
• Flash Point: 127.801°C
• Appearance: /
• Density: 0.963g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.469
• CAS DataBase Reference: 1-Boc-4-(2-propen-1-yl)-piperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Boc-4-(2-propen-1-yl)-piperidine(206446-47-1)
• EPA Substance Registry System: 1-Boc-4-(2-propen-1-yl)-piperidine(206446-47-1)

Safety Data

• Hazardous Substances Data: 206446-47-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H23NO2/c1-5-6-11-7-9-14(10-8-11)12(15)16-13(2,3)4/h5,11H,1,6-10H2,2-4H3

Upstream product

• 1779-49-3 Methyltriphenylphosphonium bromide 
• 89151-44-0 4-(2-hydroxyethyl)piperidine-1-carboxylic acid tert-butyl ester 
• 2622-05-1 allylmagnesium bromide 
• 301673-14-3 tert-butyl 4-iodopiperidine-1-carboxylate 
• 107-05-1 3-chloroprop-1-ene 
• 180695-79-8 tert-butyl 4-bromo-1-piperidinecarboxylate 
• 35466-83-2 allyl methyl carbonate 
• 84358-13-4 N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid 
• 1334681-15-0 (E)-tert-butyl 4-(3-bromoprop-1-en-1-yl)piperidine-1-carboxylate 
• 1192063-88-9 (E)-tert-butyl 4-(3-hydroxyprop-1-en-1-yl)piperidine-1-carboxylate 
• 137076-22-3 tert butyl 4-formylpiperidine-1-carboxylate 
• 198895-61-3 t-butyl 4-(3-ethoxy-3-oxoprop-1-enyl)-tetrahydropyridine-1(2H)-carboxylate 
• 109384-19-2 t-butyl 4-hydroxy piperidine-1-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 1215013-93-6 tert-butyl 4-(3-(3,5-dichloro-4-(N-(difluoromethyl)-N-(1,3,5-trimethyl-1H-pyrazol-4-yl)sulfamoyl)phenyl)propyl)-piperidine-1-carboxylate 
• 1215012-88-6 2,6-dichloro-4-(3-(1-methylpiperidin-4-yl)propyl)-N-(2,2,2-trifluoroethyl)-N-(1,3,5-trimethyl-1H-pyrazol-4-yl)benzenesulfonamide 
• 1215012-74-0 2,6-dichloro-N-(difluoromethyl)-4-(3-(1-methylpiperidin-4-yl)propyl)-N-(1,3,5-trimethyl-1H-pyrazol-4-yl)benzenesulfonamide 

Relevant articles and documents

Organophotoredox/palladium dual catalytic decarboxylative Csp3-Csp3coupling of carboxylic acids and π-electrophiles

A dual catalytic decarboxylative allylation and benzylation method for the construction of new C(sp3)-C(sp3) bonds between readily available carboxylic acids and functionally diverse carbonate electrophiles has been developed. The new process is mild, operationally simple, and has greatly improved upon the efficiency and generality of previous methodology. In addition, new insights into the reaction mechanism have been realized and provide further understanding of the harnessed reactivity.

Cobalt-Catalyzed Cross-Coupling of 3- and 4-Iodopiperidines with Grignard Reagents

A cobalt-catalyzed cross-coupling between 3- and 4-iodopiperidines and Grignard reagents is disclosed. The reaction is an efficient, cheap, chemoselective, and flexible way to functionalize piperidines. This coupling was used as the key step to realize a short synthesis of (±)-preclamol. Some mechanistic investigations were conducted that highlight the formation of radical intermediates. Scaffold synthesis: A cobalt-catalyzed cross-coupling between iodopiperidines and Grignard reagents is reported (see scheme; PG=protecting group). A large variety of 3- and 4-substituted piperidines were synthesized and the method was applied to a short synthesis of (±)-preclamol. This work constitutes one of the rare examples of cross-couplings involving 3-halogeno piperidines.

Lead optimization of a pyrazole sulfonamide series of trypanosoma brucei N -myristoyltransferase inhibitors: Identification and evaluation of CNS penetrant compounds as potential treatments for stage 2 human african trypanosomiasis

Trypanosoma brucei N-myristoyltransferase (TbNMT) is an attractive therapeutic target for the treatment of human African trypanosomiasis (HAT). From previous studies, we identified pyrazole sulfonamide, DDD85646 (1), a potent inhibitor of TbNMT. Although this compound represents an excellent lead, poor central nervous system (CNS) exposure restricts its use to the hemolymphatic form (stage 1) of the disease. With a clear clinical need for new drug treatments for HAT that address both the hemolymphatic and CNS stages of the disease, a chemistry campaign was initiated to address the shortfalls of this series. This paper describes modifications to the pyrazole sulfonamides which markedly improved blood-brain barrier permeability, achieved by reducing polar surface area and capping the sulfonamide. Moreover, replacing the core aromatic with a flexible linker significantly improved selectivity. This led to the discovery of DDD100097 (40) which demonstrated partial efficacy in a stage 2 (CNS) mouse model of HAT.