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43798

Sigma-Aldrich

Ethyl 1,3-dithiolane-2-carboxylate

≥98.0%

Synonym(s):

Glyoxylic acid ethyl ester ethylene mercaptal

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About This Item

Empirical Formula (Hill Notation):
C6H10O2S2
CAS Number:
20461-99-8
Molecular Weight:
178.27
Beilstein/REAXYS Number:
118157
EC Number:
243-837-9
MDL number:
MFCD00005411
UNSPSC Code:
12352100
PubChem Substance ID:
24867412

assay

≥98.0%

refractive index

n20/D 1.539 (lit.)
n20/D 1.540

bp

85 °C/0.1 mmHg (lit.)

density

1.249 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)C1SCCS1

InChI

1S/C6H10O2S2/c1-2-8-5(7)6-9-3-4-10-6/h6H,2-4H2,1H3

InChI key

OMCSHTHLIQOHDD-UHFFFAOYSA-N

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General description

Ethyl 1,3-dithiolane-2-carboxylate is an α-keto acid equivalent. It participates in the conjugate additions to enones. It is a bulky equivalent of acetate undergoing syn-selective aldol reactions. Anion derived from ethyl 1,3-dithiolane-2-carboxylate participates as nucleophile during the total synthesis of the corynanthe alkaloid dihydrocorynantheol and the formal syntheses of the indole alkaloids tacamonine, rhynchophylline and hirsutine. It also participates in the conjugate addition of enolates to phenylglycinol-derived α,β-unsaturated δ-lactams.

Other Notes

α-Keto acid equivalent; conjugate additions to enones ; bulky equivalent of acetate undergoing syn-selective aldol reactions

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves

Certificates of Analysis (COA)

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H. Paulson et al.
Chemische Berichte, 110, 2127-2127 (1977)
Alexander Deiters et al.
The Journal of organic chemistry, 71(17), 6547-6561 (2006-08-12)
We report herein the total synthesis of the corynanthe alkaloid dihydrocorynantheol and the formal syntheses of the indole alkaloids tacamonine, rhynchophylline, and hirsutine. The strategies for assembling the corynanthe and tacaman skeletal frameworks comprised of both the classical ABD -->
M. Kato et al.
Chemistry Letters (Jpn), 213-213 (1984)
Mercedes Amat et al.
Organic letters, 4(16), 2787-2790 (2002-08-03)
[reaction: see text] Starting from a common chiral bicyclic lactam 11, enantiopure trans- or cis-3-ethyl-4-piperidineacetate derivatives are obtained by conjugate addition of an enolate or a cuprate to the unsaturated lactams 12 or 18, respectively.
L.A. Flippin et al.
Tetrahedron Letters, 26, 2977-2977 (1985)

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