ChemicalBook--->CAS DataBase List--->847416-99-3

847416-99-3

847416-99-3 Structure

847416-99-3 Structure
IdentificationBack Directory
[Name]

INDEX NAME NOT YET ASSIGNED
[CAS]

847416-99-3
[Synonyms]

ML213
3-(Boc-aMino)cyclopentanone
1-(Boc-amino)-3-oxocyclopentane
1,1-Dimethylethyl N-(3-oxocyclopentyl)carbamate
(3-Oxo-cyclopentyl)-carbamic acid tert-butyl ester
Carbamic acid, N-(3-oxocyclopentyl)-, 1,1-dimethylethyl ester
[Molecular Formula]

C10H17NO3
[MDL Number]

MFCD09751875
[MOL File]

847416-99-3.mol
[Molecular Weight]

199.25
Chemical PropertiesBack Directory
[Boiling point ]

319.2±31.0 °C(Predicted)
[density ]

1.07±0.1 g/cm3(Predicted)
[storage temp. ]

Inert atmosphere,2-8°C
[pka]

11.89±0.20(Predicted)
[Appearance]

White to off-white Solid
[InChI]

InChI=1S/C10H17NO3/c1-10(2,3)14-9(13)11-7-4-5-8(12)6-7/h7H,4-6H2,1-3H3,(H,11,13)
[InChIKey]

CLOXAWYNXXEWBT-UHFFFAOYSA-N
[SMILES]

C(OC(C)(C)C)(=O)NC1CCC(=O)C1
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H335-H315-H302-H319
[Precautionary statements ]

P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P-P264-P270-P301+P312-P330-P501
[HS Code ]

2924297099
Hazard InformationBack Directory
[Uses]

ML-213 is a selective KV7.2 (KCNQ2) and KV7.4 (KCNQ4) channel opener (EC50 values are 230 and 510 nM for KV7.2 and KV7.4 respectively). ML-213 displays >80-fold selectivity against KV7.1, KV7.3 and KV7.5 in a thallium-based fluorescence assay.
[Synthesis]

2-Cyclopenten-1-one

930-30-3

tert-Butyl carbamate

4248-19-5

Carbamic acid, N-?(3-?oxocyclopentyl)?-?, 1,?1-?dimethylethyl ester

847416-99-3

To a stirred suspension of cyclopent-2-en-1-one (2.50 g, 30.5 mmol) in dichloromethane (60 mL) was added tert-butyl carbamate (3.60 g, 30.5 mmol) and the reaction was stirred for 10-15 minutes. Subsequently, bismuth nitrate (14.70 g, 30.5 mmol) was added in batches and stirring was continued for about 5 hours at room temperature. After completion of the reaction, the reaction mixture was diluted with dichloromethane and filtered through a bed of diatomaceous earth. The filtrate was quenched with saturated sodium bicarbonate solution and the dichloromethane layer was separated. The aqueous layer was extracted with dichloromethane, the organic extracts were combined, dried with anhydrous sodium sulfate and concentrated to give the crude product. The crude product was purified by combiflash chromatography system using hexane solution of 10-15% ethyl acetate as eluent to give tert-butyl (3-oxocyclopentyl)carbamate as white solid (6.50 g, 36% yield). Mass spectrum (MS): 200.20 (M + H).

[References]

[1] Patent: WO2015/25197, 2015, A1. Location in patent: Paragraph 000136
Spectrum DetailBack Directory
[Spectrum Detail]

INDEX NAME NOT YET ASSIGNED(847416-99-3)1HNMR
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