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Merck

798843

Sigma-Aldrich

SnAP 3Me-M Reagent

Synonym(e):

1-[(Tributylstannyl)methoxy]-2-propanamine

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About This Item

Empirische Formel (Hill-System):
C16H37NOSn
CAS-Nummer:
Molekulargewicht:
378.18
UNSPSC-Code:
12352103
PubChem Substanz-ID:
NACRES:
NA.22

Beschreibung

Flash point (deg F): >230

Qualitätsniveau

Form

liquid

Brechungsindex

n/D 1.479

Dichte

1.102 at 25 °C

Lagertemp.

−20°C

SMILES String

CCCC[Sn](CCCC)(COCC(N)C)CCCC

InChI

1S/C4H10NO.3C4H9.Sn/c1-4(5)3-6-2;3*1-3-4-2;/h4H,2-3,5H2,1H3;3*1,3-4H2,2H3;

InChIKey

HWVHQCDLUIMLHX-UHFFFAOYSA-N

Verwandte Kategorien

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 requires mild reaction conditions, and aldehydes bearing aryl, heteroaryl, glyoxyl, aliphatic, and halogenated groups are well tolerated. This product was introduced in collaboration with the 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
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)
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

Protokolle

SnAP Reagents facilitate synthesis of saturated N-heterocycles for diverse structures.

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