Merck
CN
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文件

47714

Sigma-Aldrich

N-甲基吡啶-4-羰甲醛苯磺酸盐

≥95.0%

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经验公式（希尔记法）:
C13H13NO4S
CAS号:
82228-89-5
分子量:
279.31
Beilstein:
5695963
MDL编号:
MFCD00043164
PubChem化学物质编号:
57651088
NACRES:
NA.22

质量水平

100

检测方案

≥95.0%

形式

solid

杂质

≤2.0% water

mp

~95 °C

SMILES string

[H]C(=O)c1cc[n+](C)cc1.[O-]S(=O)(=O)c2ccccc2

InChI

1S/C7H8NO.C6H6O3S/c1-8-4-2-7(6-9)3-5-8;7-10(8,9)6-4-2-1-3-5-6/h2-6H,1H3;1-5H,(H,7,8,9)/q+1;/p-1

InChI key

HSVLGIFAXFDLMU-UHFFFAOYSA-M

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相关类别

一般描述

4-Formyl-1-methylpyridinium benzenesulfonate is a pyridinium salt widely used for the conversion of primary amines to the carbonyl compounds like aldehydes and ketones. The reaction conditions are mild, suitable for compounds with sensitive functional groups thereby providing an efficient alternative for such transformations.

应用

4-Formyl-1-methylpyridinium benzenesulfonate may be used as a reagent in the synthesis of the following:
  • tetrazolic analogs of chalcones
  • (+)-ferruginol
  • Ecteinascidin 743
  • Galipea alkaloids

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)

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Mild and simple biomimetic conversion of amines to carbonyl compounds.
Buckley TF and Rapoport H
Journal of the American Chemical Society, 104(16), 4446-4450 (1982)
Ornella Mesenzani et al.
Bioorganic & medicinal chemistry letters, 21(2), 764-768 (2010-12-21)
In the chalcone scaffold, it is thought that the double bond is an important structural linker but it is likely not essential for the interaction with tubulin. Yet, it may be a potential site of metabolic degradation and interaction with
Jinchun Chen et al.
Journal of the American Chemical Society, 128(1), 87-89 (2006-01-05)
A convergent total synthesis of ecteinascidin 743 is realized from five building blocks of almost equal size. It takes 23 steps from l-3-hydroxy-4-methoxy-5-methyl phenylalanol (5) with an overall yield of 3%.
Short syntheses of (+)-ferruginol from (+)-dehydroabietylamine.
Gonzalez MA and Perez-Guaita D.
Tetrahedron, 68(47), 9612-9615 (2012)
Zacharias Amara et al.
Natural product reports, 30(9), 1211-1225 (2013-07-31)
This review focuses on recent applications of the aza-Michael reaction in alkaloids total synthesis with a special emphasis on stereoselectivity. The report highlights achievements and challenges over the past five years and describes stereoselective intra- and inter-molecular conjugate addition of

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