| Identification | Back Directory | [Name]
Carbamic acid, 4-pentynyl-, 1,1-dimethylethyl ester (9CI) | [CAS]
151978-50-6 | [Synonyms]
N-Boc-4-pentyne-1-aMine
N-Boc-5-amino-1-pentyne
tert-butyl pent-4-ynylcarbamate
tert-Butyl (4-pentynyl)carbamate
N-Boc-4-pentyne-1-amine >=95% (GC)
tert-Butyl pent-4-yn-1-ylcarbamate
4-Pentynylcarbamic acid tert-butyl ester
N-(tert-butoxycarbonyl)-pent-4-ynyl-1-amine
N-(Pent-4-ynyl)carbamic acid tert-butyl ester
Carbamic acid, 4-pentynyl-, 1,1-dimethylethyl ester
CarbaMic acid, N-4-pentyn-1-yl-, 1,1-diMethylethyl ester
Carbamic acid, 4-pentynyl-, 1,1-dimethylethyl ester (9CI) | [Molecular Formula]
C10H17NO2 | [MDL Number]
MFCD20036287 | [MOL File]
151978-50-6.mol | [Molecular Weight]
183.25 |
| Chemical Properties | Back Directory | [Boiling point ]
267.2±23.0 °C(Predicted) | [density ]
0.965±0.06 g/cm3(Predicted) | [storage temp. ]
Storage temp. 2-8°C | [form ]
Solid | [pka]
12.61±0.46(Predicted) | [color ]
White to off-white | [BRN ]
6918435 | [InChI]
InChI=1S/C10H17NO2/c1-5-6-7-8-11-9(12)13-10(2,3)4/h1H,6-8H2,2-4H3,(H,11,12) | [InChIKey]
JTPJJKZSKWNWKK-UHFFFAOYSA-N | [SMILES]
C(OC(C)(C)C)(=O)NCCCC#C |
| Hazard Information | Back Directory | [Uses]
N-Boc-4-pentyne-1-amine is a PROTAC linker, which refers to the alkyl chain composition. N-Boc-4-pentyne-1-amine can be used in the synthesis of the PROTAC MG-277 (HY-130122)[1]. N-Boc-4-pentyne-1-amine is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups. | [reaction suitability]
reaction type: click chemistry | [Synthesis]
Pent-4-yn-1-amine (4.91 g, 59.06 mmol, 1.00 eq.) was dissolved in dichloromethane (40 mL) at 0 °C, followed by triethylamine (8.95 g, 88.45 mmol, 1.50 eq.). A solution of di-tert-butyl dicarbonate (12.88 g, 59.02 mmol, 1.00 eq.) in dichloromethane (20 mL) was added dropwise with stirring. The reaction mixture was gradually warmed to room temperature and stirred at that temperature overnight. Upon completion of the reaction, the mixture was concentrated under reduced pressure and subsequently purified by silica gel column chromatography (eluent: ethyl acetate/petroleum ether from 1:50 to 1:40) to afford N-BOC-4-pentyn-1-amine (4.59 g, 43% yield) as a light yellow oil. | [IC 50]
Alkyl/ether | [References]
[1] Yang J, et al. Simple Structural Modifications Converting a Bona fide MDM2 PROTAC Degrader into a Molecular Glue Molecule: A Cautionary Tale in the Design of PROTAC Degraders. J Med Chem. 2019 Oct 21. DOI:10.1021/acs.jmedchem.9b00846 |
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