tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate

• ChemBase ID: 29867
• Molecular Formular: C16H28BNO4
• Molecular Mass: 309.20882
• Monoisotopic Mass: 309.21113878
• SMILES: C1(=CCN(CC1)C(=O)OC(C)(C)C)B1OC(C(O1)(C)C)(C)C
• Canonical SMILES: O=C(N1CCC(=CC1)B1OC(C(O1)(C)C)(C)C)OC(C)(C)C
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate
• IUPAC Traditional name: tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate
• Synonyms: tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate; tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborol-an-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate; (1-tert-Butoxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)boronic acid pinacol ester; (N-tert-Butoxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)boronic acid pinacol ester; (N-tert-Butoxycarbonyl-1,2,5,6-tetrahydropyridin-4-yl)boronic acid pinacol ester; (N-tert-Butoxycarbonyl)-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester; N-Boc-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester; tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate; tert-Butyl 3,6-dihydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-1(2H)-carboxylate; 1,2,3,6-Tetrahydropyridine-4-boronic acid, pinacol ester, N-BOC protected; N-(tert-butoxycarbonyl)-3,6-dihydro-2H-pyridine-4-boronic acid pinacol ester; [1-Boc-1,2,3,6-tetrahydropyridine-4-yl]boronic acid pinacol ester; N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester; tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate; (N-叔丁氧羰基)-1,2,3,6-四氢吡啶-4-硼酸频哪醇酯; N-Boc-1,2,3,6-四氢吡啶-4-硼酸频哪醇酯

Database IDs

• CAS Number: 286961-14-6
• MDL Number: MFCD03840345
• PubChem SID: 160993174
• PubChem CID: 4642098

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.6289
• LogD (pH = 7.4): 2.6289
• Log P: 2.6289
• Molar Refractivity: 82.3596 cm^3
• Polarizability: 33.774742 Å^3
• Polar Surface Area: 48.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 100-114 °C; 115-117°C
• Hydrophobicity(logP): 3.606

Safety Information

• Storage Warning: Harmful/Irritant/Keep Cold/Store under Argon; IRRITANT
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95%; 96%; 97%; 98%
• Empirical Formula (Hill Notation): C16H28BNO4

DETAILS

Sigma Aldrich - 706531

Packaging
1 g in glass bottle
250 mg in glass bottle
Application
Reagent used for
• Suzuki-Miyaura cross-coupling using palladium phosphine catalyst1
• Palladium-catalyzed ligand-controlled regioselective Suzuki coupling2
• Palladium-catalyzed Suzuki-Miyaura coupling3
• Suzuki coupling followed by iodolactonization reaction4
• Wrenchnolol derivative optimized for gene activation in cells5 Reagent used in Preparation of several enzymatic inhibitors and receptor ligands
• Orally active anaplastic lymphoma kinase inhibitors6
• Oxazolecarboxamides as diacylglycerol acyltransferase-1 inhibitors for treatment of obesity and diabetes7
• 4-arylpiperidinyl amides and N-arylpiperidin-3-yl-cyclopropanecarboxamides as novel melatonin receptor ligands8
• Quinazoline analogs as glucocerebrosidase inhibitors with chaperone activity for treatment of Gaucher disease, a lysosomal storage disorder9
• Arylpiperazine and piperidine ethers as dual acting norepinephrine reuptake inhibitors and 5-HT1A partial agonists10