43798
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:
Molecular Weight:
178.27
Beilstein:
118157
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
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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 Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
235.4 °F - closed cup
Flash Point(C)
113 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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M. Kato et al.
Chemistry Letters (Jpn), 213-213 (1984)
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 -->
H. Paulson et al.
Chemische Berichte, 110, 2127-2127 (1977)
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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