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About This Item
经验公式（希尔记法）:
C7H12O2S2
CAS号:
分子量:
192.30
Beilstein:
1424352
EC 号:
MDL编号:
UNSPSC代码:
12352100
PubChem化学物质编号:
NACRES:
NA.22
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等级
technical
方案
≥90% (GC)
折射率
n20/D 1.539 (lit.)
n20/D 1.541
沸点
75-77 °C/0.2 mmHg (lit.)
密度
1.22 g/mL at 25 °C (lit.)
官能团
ester
thioether
SMILES字符串
CCOC(=O)C1SCCCS1
InChI
1S/C7H12O2S2/c1-2-9-6(8)7-10-4-3-5-11-7/h7H,2-5H2,1H3
InChI key
ANEDZEVDORCLPM-UHFFFAOYSA-N
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一般描述
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.
Varinder K. Aggarwal et al.
The Journal of organic chemistry, 63(21), 7306-7310 (2001-10-24)
Asymmetric oxidation of a range of 1,3-dithianes was studied using the Kagan protocol [CHP (4 equiv), (+)-DET (2 equiv), Ti(OiPr)(4) (1 equiv), and H(2)O (1 equiv) at -35 degrees C for 48 h]. 1,3-Dithiane itself gave monoxide (30% ee) and
Alkylation of the carbanion from methyl bis (ethylthio) acetate with alkyl and aralkyl halides.
Lerner LM.
The Journal of Organic Chemistry, 41(12), 2228-2229 (1976)
Aldol condensations of ethyl 1,3-dithiolane-2-carsoxylate and ethyl 1, 3-dithiane-2-carboxylate with chiral aldehydes. Exceptional diastereoface selectivity from two convenient acetate equivalents.
Flippin LA and Dombroski MA.
Tetrahedron Letters, 26(25), 2977-2980 (1985)
Convenient synthesis of α-keto esters.
Eliel EL and Hartmann AA.
The Journal of Organic Chemistry, 37(3), 505-506 (1972)
Mark Cushman et al.
The Journal of organic chemistry, 67(16), 5807-5816 (2002-08-03)
A series of 6-carboxyalkyl and 6-phosphonoxyalkyl derivatives of 7-oxo-8-D-ribityllumazine were synthesized as inhibitors of both Escherichia coli riboflavin synthase and Bacillus subtilis lumazine synthase. The compounds were designed to bind to both the ribitylpurine binding site and the phosphate binding
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