Ethyl-1,3-dithian-2-carboxylat

Bezeichnung:Ethyl-1,3-dithian-2-carboxylat

CAS-Nr20462-00-4

Englisch Name:Ethyl 1,3-dithiane-2-carboxylate

CBNumberCB6490333

SummenformelC7H12O2S2

Molgewicht192.3

MOL-Datei20462-00-4.mol

Synonyma

Ethyl-1,3-dithian-2-carboxylat

Ethyl-1,3-dithian-2-carboxylat physikalisch-chemischer Eigenschaften

Schmelzpunkt	19-21°C
Siedepunkt	75-77 °C/0.2 mmHg (lit.)
Dichte	1.22 g/mL at 25 °C (lit.)
Brechungsindex	n20/D 1.539(lit.)
Flammpunkt	130 °F
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Aggregatzustand	clear liquid
Farbe	Colorless to Light yellow to Light orange
Wasserlöslichkeit	Slightly miscible with water.
BRN	1424352
InChI	InChI=1S/C7H12O2S2/c1-2-9-6(8)7-10-4-3-5-11-7/h7H,2-5H2,1H3
InChIKey	ANEDZEVDORCLPM-UHFFFAOYSA-N
SMILES	S1CCCSC1C(OCC)=O
CAS Datenbank	20462-00-4(CAS DataBase Reference)
NIST chemische Informationen	Ethyl 1,3-dithiane-2-carboxylate(20462-00-4)

Sicherheit

R-Sätze:	10
S-Sätze:	26-36/37/39-45
RIDADR	UN 3272 3/PG 3
WGK Germany	3
F	9-13
HazardClass	3
PackingGroup	III
HS Code	29349990

Gefahreninformationscode (GHS)

Ethyl 1,3-dithiane-2-carboxylate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R10:Entzündlich.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
Chemische Eigenschaften
clear yellowish liquid
Verwenden
Ethyl 1,3-dithiane-2-carboxylate is used in syn-selective aldol reactions. It undergoes asymmetric oxidation to give trans bis-sulfoxide. It is used to generate carbanon, which finds application in the preparation of alfa- keto esters.
synthetische
To a solution of BF3. Et2O (57.5 mL, 0.454 mmol) in CHC13 (180 mL) heated at reflux was added dropwise, over a 1h period, a solution of 1,3-propanedithiol (22.7 mL, 0.227 mmol), followed by ethyl diethoxyacetate (40 g, 0.227 mmol) in CHCl3 (40 mL). The resulting mixture was heated for 30 minutes, and then cooled to rt. The cooled solution was washed 2 times with water, once with saturated aqueous NaHC03, and then re-washed with water. The combined organic phases were dried over MgS04, then evaporated to give 41 g (94%) of Ethyl 1,3-dithiane-2-carboxylate as a yellow oi. Yield: 94%
Application
Ethyl 1,3-dithiane-2-carboxylate is a synthetic compound that is used in the synthesis of organic compounds . It is used in asymmetric synthesis to produce chiral products from achiral starting materials. The desulfurization reaction of ethyl 1,3-dithiane-2-carboxylate produces a mixture of the two possible stereoisomers of the product. This mixture can be separated by phase chromatography and then hydrolyzed to give the desired product. In dyslipidemia, ethyl 1,3-dithiane-2-carboxylate inhibits the activity of hepatic lipase and acidolysis. This inhibition leads to an increase in serum triglycerides and cholesterol levels. This compound also has been shown to have antiplatelet properties when administered orally or intravenously to rats without affecting platelet aggregation rates.
Synthesis Reference(s)
Synthetic Communications, 11, p. 343, 1981 DOI: 10.1080/00397918108063615
Allgemeine Beschreibung
Ethyl 1,3-dithiane-2-carboxylate is an α-keto acid equivalent and bulky equivalent of acetate. It participates in syn-selective aldol reactions. It can be prepared from the reaction of ethyl diethoxyacetate and 1,3-propanedithiol in the presence of BF₃/Et₂O. Asymmetric oxidation of ethyl 1,3-dithiane-2-carboxylate by Modena protocol has been reported to afford trans bis-sulfoxide in 60% yield. Carbanion from ethyl 1,3-dithiane-2-carboxylate may be employed for the preparation of α-keto esters.
läuterung methode
Dissolve the ester in CHCl3, wash with aqueous K2CO3, twice with H2O, dry over MgSO4, filter, evaporate and distil the residue. [Eliel & Hartman J Org Chem 37 505 1972, Seebach Synthesis 1 17 1969, Beilstein 19/7 V 227.]

Ethyl 1,3-dithiane-2-carboxylate Upstream-Materialien And Downstream Produkte

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