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798886

Sigma-Aldrich

SnAP TM Reagent

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About This Item

Fórmula empírica (notación de Hill):
C15H35NSSn
Número de CAS:
1452829-00-3
Peso molecular:
380.22
Número MDL:
MFCD23703162
Código UNSPSC:
12352103
ID de la sustancia en PubChem:
329768678
NACRES:
NA.22

formulario

liquid

Nivel de calidad

100

índice de refracción

n/D 1.512

densidad

1.158 at 25 °C

grupo funcional

amine
thioether

temp. de almacenamiento

−20°C

cadena SMILES

CCCC[Sn](CCCC)(CSCCN)CCCC

InChI

1S/3C4H9.C3H8NS.Sn/c3*1-3-4-2;1-5-3-2-4;/h3*1,3-4H2,2H3;1-4H2;

Clave InChI

DYBMHPJDHUKXRF-UHFFFAOYSA-N

Descripción general

SnAP (Sn amino protocol) reagents have been developed by the Bode group. SnAP reagents are air and moisture stable. They can be prepared from simple reactions with cheap raw materials. SnAP 2-Spiro-(4-Pip) M, also referred to as SnAP 2-spiro-(4-piperdine) morpholine, is a regioisomeric SnAP reagent. This reagent can be prepared from N-Boc piperidone.

Aplicación

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
SnAP TM Reagent may be used to synthesize 3-substituted thiomorpholines from aldehydes. It may also be used in the preparation of unprotected, saturated N-heterocyclic compounds.

Automate your N-heterocycle formation with Synple Automated Synthesis Platform (SYNPLE-SC002)

Otras notas

Technology spotlight: SnAP Reagents
Professor product portal: Jeffrey Bode Research Group
SnAP Reagents for the Synthesis of Piperazines and Morpholines
SnAP reagents for the one-step synthesis of medium-ring saturated N-heterocycles from aldehydes
SnAP Reagents for a Cross-Coupling Approach to the One-Step Synthesis of Saturated N-Heterocycles
Bespoke SnAP Reagents for the Synthesis of C-Substituted Spirocyclic and Bicyclic Saturated N-Heterocycles

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Palabra de señalización

Danger

Clasificaciones de peligro

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

Código de clase de almacenamiento

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

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
MKBX2274V
MKBZ4437V

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SnAP Reagents for a Cross-Coupling Approach to the One-Step Synthesis of Saturated N-Heterocycles.
Luescher MU, et al.
Aldrichimica Acta, 48(2), 43-48 (2015)
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)

Protocolos

SnAP Reagents

Saturated N-heterocyclic building blocks or SnAP Reagents are of growing importance for the convenient synthesis of medium-ring saturated N-heterocycles, including bicyclic and spirocyclic structures. SnAP reagents are stable and readily available and can be coupled with widely available aromatic, heteroaromatic, aliphatic, and glyoxylic aldehydes.

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