43798
1,3-二硫烷-2-甲酸乙酯
≥98.0%
别名:
1,3-二硫戊环-2-甲酸乙酯
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关于此项目
经验公式（希尔记法）:
C6H10O2S2
化学文摘社编号:
分子量:
178.27
EC Number:
243-837-9
UNSPSC Code:
12352100
PubChem Substance ID:
Beilstein/REAXYS Number:
118157
MDL number:
Assay:
≥98.0%
InChI key
OMCSHTHLIQOHDD-UHFFFAOYSA-N
InChI
1S/C6H10O2S2/c1-2-8-5(7)6-9-3-4-10-6/h6H,2-4H2,1H3
SMILES string
CCOC(=O)C1SCCS1
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.)
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-酮酸等价物；对烯酮的共轭加成；进行顺式选择性羟醛反应的乙酸酯大位阻等价物
存储类别
10 - Combustible liquids
wgk
WGK 3
flash_point_f
235.4 °F - closed cup
flash_point_c
113 °C - closed cup
ppe
Eyeshields, Gloves
法规信息
新产品
此项目有
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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