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Merck

706531

Sigma-Aldrich

N-Boc-1,2,3,6-Tetrahydropyridin-4-Boronsäurepinakolester

95%

Synonym(e):

(N-tert.-Butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-boronsäure-pinakolester

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About This Item

Empirische Formel (Hill-System):
C16H28BNO4
CAS-Nummer:
Molekulargewicht:
309.21
MDL-Nummer:
UNSPSC-Code:
12352103
PubChem Substanz-ID:
NACRES:
NA.22

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Qualitätsniveau

Assay

95%

Form

powder

mp (Schmelzpunkt)

100-114 °C

SMILES String

CC(C)(C)OC(=O)N1CCC(=CC1)B2OC(C)(C)C(C)(C)O2

InChI

1S/C16H28BNO4/c1-14(2,3)20-13(19)18-10-8-12(9-11-18)17-21-15(4,5)16(6,7)22-17/h8H,9-11H2,1-7H3

InChIKey

VVDCRJGWILREQH-UHFFFAOYSA-N

Allgemeine Beschreibung

Boc-THP-Bpin is frequently used in metal catalyzed cross-coupling reactions, such as Suzuki-Miyaura and Negishi couplings.[1][2]

Anwendung

Reagent used for
  • Suzuki-Miyaura cross-coupling using palladium phosphine catalyst[1]
  • Palladium-catalyzed ligand-controlled regioselective Suzuki coupling[2]
  • Palladium-catalyzed Suzuki-Miyaura coupling[3]
  • Suzuki coupling followed by iodolactonization reaction[4]
  • Wrenchnolol derivative optimized for gene activation in cells[5]

Reagent used in Preparation of several enzymatic inhibitors and receptor ligands
  • Orally active anaplastic lymphoma kinase inhibitors[6]
  • Oxazolecarboxamides as diacylglycerol acyltransferase-1 inhibitors for treatment of obesity and diabetes[7]
  • 4-arylpiperidinyl amides and N-arylpiperidin-3-yl-cyclopropanecarboxamides as novel melatonin receptor ligands[8]
  • Quinazoline analogs as glucocerebrosidase inhibitors with chaperone activity for treatment of Gaucher disease, a lysosomal storage disorder[9]
  • Arylpiperazine and piperidine ethers as dual acting norepinephrine reuptake inhibitors and 5-HT1A partial agonists[10]

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)


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Die Dokumentenbibliothek aufrufen

Design and synthesis of 4-arylpiperidinyl amide and N-arylpiperidin-3-yl-cyclopropanecarboxamide derivatives as novel melatonin receptor ligands
Li, G.; et al.
Bioorganic & Medicinal Chemistry, 21, 1236-1242 (2011)
Neil A Strotman et al.
The Journal of organic chemistry, 75(5), 1733-1739 (2010-02-10)
Various dihaloazoles can be monoarylated at a single C-X bond with high selectivity via Suzuki coupling. By changing the palladium catalyst employed, the selectivity can be switched for some dihaloazoles, allowing for Suzuki coupling at the other, traditionally less reactive
Paul M Wehn et al.
Organic letters, 11(24), 5666-5669 (2009-12-17)
A novel approach to the synthesis of substituted 5-amino- and 3-amino-1,2,4-thiadiazoles beginning from a common precursor has been achieved. Derivatization by palladium-catalyzed Suzuki-Miyaura coupling enables the rapid preparation of analogs around this pharmaceutically relevant core. FMO calculations rationalize the observed
Preparation of 3,4-fused-spiro[furan-5(5H),4'-piperidin]-2-one
Liu, J.; et al.
Tetrahedron Letters, 50, 5228-5230 (2009)
Kazutomo Kinoshita et al.
Bioorganic & medicinal chemistry, 20(3), 1271-1280 (2012-01-10)
Anaplastic lymphoma kinase (ALK) receptor tyrosine kinase is considered an attractive therapeutic target for human cancers, especially non-small cell lung cancer (NSCLC). Our previous study revealed that 8,9-side-chains of 6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole scaffold crucially affected kinase selectivity, cellular activity, and metabolic stability.

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