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About This Item
经验公式（希尔记法）:
C6H10O2S2
CAS号:
分子量:
178.27
Beilstein:
118157
EC 号:
MDL编号:
UNSPSC代码:
12352100
PubChem化学物质编号:
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方案
≥98.0%
折射率
n20/D 1.539 (lit.)
n20/D 1.540
沸点
85 °C/0.1 mmHg (lit.)
密度
1.249 g/mL at 25 °C (lit.)
SMILES字符串
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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一般描述
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.
其他说明
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
储存分类代码
10 - Combustible liquids
WGK
WGK 3
闪点(°F)
235.4 °F - closed cup
闪点(°C)
113 °C - closed cup
个人防护装备
Eyeshields, Gloves
法规信息
新产品
H. Paulson et al.
Chemische Berichte, 110, 2127-2127 (1977)
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 -->
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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