184246-38-6

Basic information

• Product Name: 2-Propenal, 2-methyl-3-(2-methyl-4-thiazolyl)-, (2E)-
• CAS NO: 184246-38-6
• Molecular Formula: C8H9NOS
• Molecular Weight: 167.232
• Mol File: 184246-38-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-Propenal, 2-methyl-3-(2-methyl-4-thiazolyl)-, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenal, 2-methyl-3-(2-methyl-4-thiazolyl)-, (2E)-(184246-38-6)
• EPA Substance Registry System: 2-Propenal, 2-methyl-3-(2-methyl-4-thiazolyl)-, (2E)-(184246-38-6)

Safety Data

• Hazardous Substances Data: 184246-38-6(Hazardous Substances Data)

Usage

Physical Properties

Yellow liquid

Odor

Sharp, sweet, nutty

Solubility

Soluble in water and organic solvents

Uses

Flavoring agent in the food industry
Fragrance ingredient in the cosmetic and perfume industry
Synthesis of pharmaceuticals and organic compounds

Hazards

Strong irritant to the skin, eyes, and respiratory system

Upstream product

• 6436-59-5 ethyl 2-methylthiazole-4-carboxylate 

Downstream Products

• 152044-54-7 epothilone B 
• 186692-70-6 Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-(tert-butyl-dimethyl-silanyloxy)-8,10,12,12-tetramethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-13-oxo-11-triphenylsilanyloxy-tridec-3-enyl ester 
• 186692-71-7 (Z)-(4S,6R,7R,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-6-triphenylsilanyloxy-oxacyclohexadec-13-en-2-one 
• 186692-69-3 Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-(tert-butyl-dimethyl-silanyloxy)-13,13-dimethoxy-8,10,12,12-tetramethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-11-triphenylsilanyloxy-tridec-3-enyl ester 
• 184246-43-3 4-{(E)-2-[(2S,4S)-4-(4-Methoxy-benzyloxy)-3,4-dihydro-2H-pyran-2-yl]-propenyl}-2-methyl-thiazole 
• 189453-35-8 (4S,7R,8S,9S,13Z,16S,1'E)-4,8-di-tert-butyldimethylsilyloxy-5,5,7,9,13-pentamethyl-16-[1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-1-oxa-13-cyclohexadecene-2,6-dione 
• 189453-30-3 Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-(tert-butyl-dimethyl-silanyloxy)-4,8,10,12,12-pentamethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-13-oxo-11-triphenylsilanyloxy-tridec-3-enyl ester 
• 189453-32-5 (Z)-(6R,7R,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-6-triphenylsilanyloxy-oxacyclohexadec-13-ene-2,4-dione 
• 189453-27-8 Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-(tert-butyl-dimethyl-silanyloxy)-13,13-dimethoxy-4,8,10,12,12-pentamethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-11-triphenylsilanyloxy-tridec-3-enyl ester 
• 189453-47-2 (Z)-(4R,6R,7R,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-6-triphenylsilanyloxy-oxacyclohexadec-13-en-2-one 
• 189453-43-8 (Z)-(4S,6R,7R,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-6-triphenylsilanyloxy-oxacyclohexadec-13-en-2-one 
• 189453-10-9 epothilone D 
• 184246-44-4 Formic acid (1S,3S)-3-(4-methoxy-benzyloxy)-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-4-oxo-butyl ester 
• 184246-45-5 Formic acid (1S,3S,4S)-4-hydroxy-3-(4-methoxy-benzyloxy)-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-hept-6-enyl ester 

Relevant articles and documents

Enantioselective total synthesis of epothilone A using multifunctional asymmetric catalyses

A catalytic version has now been developed for the enantioselective total synthesis of epothilone A (1). The key is the use of multifunctional asymmetric catalySes for a direct aldol reaction and cyanosilylation. This successful approach demonstrated the usefulness of these reactions for the catalytic asymmetric synthesis of complex molecules.

Total syntheses of epothilones A and B via a macrolactonization-based strategy

The total syntheses of epothilones A (1) and B (2) and several analogues thereof are described. The reported strategy relies on a macrolactonization approach and features selective epoxidation of the macrocycle double bond in precursors 3 and 4 (Scheme 1), respectively, as well as high convergency and flexibility. Building blocks 9-12 and 15 were constructed by asymmetric processes and coupled via Wittig, aldol, and macrolactonization reactions to afford the basic skeleton of epothilones and that of several of their analogues by a relatively short route. The utilization ofintermediate 14, obtained via a stereoselective Wittig reaction and its Enders coupling to SAMP hydrazone 13 (Scheme 8), in combination with a stereoselective aldol reaction with the modified substrate 69 (Scheme 10) improved the stereoselectivity and efficiency of the total synthesis of these new and highly potent microtubule binding antitumor agents.