155160

Sigma-Aldrich

Tetrahydro-4H-thiopyran-4-one

99%

Empirical Formula (Hill Notation):
C5H8OS
CAS Number:
Molecular Weight:
116.18
Beilstein/REAXYS Number:
106464
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

99%

mp

60-64 °C (lit.)

SMILES string

O=C1CCSCC1

InChI

1S/C5H8OS/c6-5-1-3-7-4-2-5/h1-4H2

InChI key

OVRJVKCZJCNSOW-UHFFFAOYSA-N

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General description

The diastereoselectivity of the aldol reaction of tetrahydro-4H-thiopyran-4-one has been studied.

Application

The product has been utilized in various condensation reactions for the preparation of dipeptides, spiroimidazolones, and tetrahydrocarbazoles and α-hydroxy esters.
Tetrahydro-4H-thiopyran-4-one was used in the preparation of meso 1,9-diketones.

Packaging

1, 5 g in glass bottle

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Synlett, 1605-1605 (2007)
Dale E Ward et al.
The Journal of organic chemistry, 67(5), 1618-1629 (2002-03-02)
The diastereoselectivity of the aldol reaction of tetrahydro-4H-thiopyran-4-one (3) with 1,4-dioxa-8-thiaspiro[4.5]decane-6-carboxaldehyde (9a) under a variety of conditions is examined. Under optimized conditions, three of the four possible diastereomers from this aldol reaction can be obtained selectively (3-16:1). Reactions of 9a...
Dale E Ward et al.
Organic letters, 8(12), 2631-2634 (2006-06-02)
Meso 1,9-diketones (six to seven stereocenters) are readily obtained by stepwise or simultaneous two-directional aldol reactions of tetrahydro-4H-thiopyran-4-one with a thiopyran-derived aldehyde or dialdehyde. Enantioselective enolizations of these diketones with the lithium amide from (R,R)-bis(1-phenylethyl)amine occur with simultaneous kinetic resolution...
Journal of Heterocyclic Chemistry, 30, 81-81 (1993)
Synthesis, 672-672 (1994)

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