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Merck

798894

Sigma-Aldrich

SnAP DA Reagent

Synonym(e):

tert-Butyl (3-aminopropyl)((tributylstannyl)methyl)carbamate

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About This Item

Empirische Formel (Hill-System):
C21H46N2O2Sn
CAS-Nummer:
Molekulargewicht:
477.31
UNSPSC-Code:
12352103
PubChem Substanz-ID:
NACRES:
NA.22

Form

liquid

Qualitätsniveau

Funktionelle Gruppe

amine
carbamate

Lagertemp.

−20°C

SMILES String

CCCC[Sn](CCCC)(CN(C(OC(C)(C)C)=O)CCCN)CCCC

InChI

1S/C9H19N2O2.3C4H9.Sn/c1-9(2,3)13-8(12)11(4)7-5-6-10;3*1-3-4-2;/h4-7,10H2,1-3H3;3*1,3-4H2,2H3;

InChIKey

IXXRAKGOXZKYBH-UHFFFAOYSA-N

Anwendung

SnAP Reagents provide a one-step route, in tandem with various aldehyde substrates, to saturated N-heterocycles. The synthesis of N-Heterocycles through SnAP Reagents require mild reaction conditions and aldehydes bearing aryl, heteroaryl, aliphatic, halogenated and glyoxylates are well tolerated. This product was introduced in collaboration with the Jeffrey Bode Research Group.

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Signalwort

Danger

Gefahreneinstufungen

Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT RE 1

Lagerklassenschlüssel

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


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Woon-Yew Siau et al.
Journal of the American Chemical Society, 136(51), 17726-17729 (2014-12-09)
The combination of cyclic ketones and stannyl amine protocol (SnAP) reagents affords saturated, spirocyclic N-heterocycles under operationally simple reaction conditions. The resulting, N-unprotected spirocyclic amines are in great demand as scaffolds for drug discovery and development. The union of SnAP
Michael U Luescher et al.
Organic letters, 16(4), 1236-1239 (2014-02-08)
Substituted piperazines and morpholines are valuable structural motifs in biologically active compounds, but are not easily prepared by contemporary cross-coupling approaches. In this report, we introduce SnAP reagents for the transformation of aldehydes into N-unprotected piperazines and morpholines. This approach
Cam-Van T Vo et al.
Nature chemistry, 6(4), 310-314 (2014-03-22)
Interest in saturated N-heterocycles as scaffolds for the synthesis of bioactive molecules is increasing. Reliable and predictable synthetic methods for the preparation of these compounds, especially medium-sized rings, are limited. We describe the development of SnAP (Sn amino protocol) reagents
SnAP reagents for the transformation of aldehydes into substituted thiomorpholines--an alternative to cross-coupling with saturated heterocycles.
Cam-Van T Vo et al.
Angewandte Chemie (International ed. in English), 52(6), 1705-1708 (2013-01-03)

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