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Sigma-Aldrich

Tetrahydro-4H-thiopyran-4-one

99%

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About This Item

Empirical Formula (Hill Notation):
C5H8OS
CAS Number:
Molecular Weight:
116.18
Beilstein:
106464
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

99%

form

crystals

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

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synlett, 1605-1605 (2007)
Journal of Heterocyclic Chemistry, 30, 81-81 (1993)
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
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
Synthesis, 672-672 (1994)

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