623-43-8 Usage
Description
Trans-Methyl crotonate, also known as trans-2-methylbut-2-enoic acid, is an organic compound that features a methyl group and a crotonate group. It is a colorless liquid with a distinctive odor and is soluble in water. trans-Methyl crotonate is a versatile building block in organic synthesis and has various applications in different industries.
Uses
Used in Chemical Synthesis:
Trans-Methyl crotonate is used as a starting reagent for the total synthesis of various organic compounds, including phytotoxins such as solanapyrones D(1) and E(2). Its unique structure allows for the formation of new chemical bonds and the creation of complex molecules.
Used in Enzymatic Reactions:
In the field of biocatalysis, trans-methyl crotonate is used to investigate chemoselectivity in reactions involving amines. For example, it has been used in a study with benzyl amine catalyzed by lipase B from Candida Antarctica, where solvent engineering was employed to enhance the reaction's selectivity and efficiency.
Used in Flavor and Fragrance Industry:
Due to its distinctive odor, trans-methyl crotonate can be used as a component in the flavor and fragrance industry. It can contribute to the development of new scents or enhance existing ones, providing a unique and pleasant aroma.
Used in Pharmaceutical Industry:
Trans-methyl crotonate has potential applications in the pharmaceutical industry as an intermediate in the synthesis of various drugs and pharmaceutical compounds. Its ability to form new chemical bonds makes it a valuable building block for creating novel therapeutic agents.
Synthesis
Trans-Methyl crotonate is obtained by esterification of crotonic acid and methanol. The reaction solution prepared by 800g of crotonic acid, 1L of methanol, 130g of sulfuric acid and 300ml of carbon tetrachloride was heated on a water bath, and carbon tetrachloride was recovered after dehydration and esterification to obtain a crude product of methyl crotonate. Then, the unreacted crotonic acid in the crude product is washed with water, washed with 5% sodium carbonate, and purified by vacuum distillation to obtain the finished product.
Synthesis Reference(s)
Tetrahedron Letters, 14, p. 2967, 1973 DOI: 10.1016/S0040-4039(01)96294-X
Check Digit Verification of cas no
The CAS Registry Mumber 623-43-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 3 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 623-43:
(5*6)+(4*2)+(3*3)+(2*4)+(1*3)=58
58 % 10 = 8
So 623-43-8 is a valid CAS Registry Number.
InChI:InChI=1/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)/p-1/b4-3+
623-43-8Relevant articles and documents
Ligand-controlled cobalt-catalyzed remote hydroboration and alkene isomerization of allylic siloxanes
Huang, Jiaxin,Li, Jie,Yang, Wen,Zhang, Kezhuo,Zhao, Pei,Zhao, Wanxiang
supporting information, p. 302 - 305 (2022/01/03)
The Co-catalyzed remote hydroboration and alkene isomerization of allylic siloxanes were realized by a ligand-controlled strategy. The remote hydroboration with dcype provided borylethers, while xantphos favored the formation of silyl enol ethers.
Second-Generation meta-Phenolsulfonic Acid-Formaldehyde Resin as a Catalyst for Continuous-Flow Esterification
Hu, Hao,Ota, Hajime,Baek, Heeyoel,Shinohara, Kenta,Mase, Toshiaki,Uozumi, Yasuhiro,Yamada, Yoichi M. A.
supporting information, p. 160 - 163 (2020/01/02)
A second-generation m-phenolsulfonic acid-formaldehyde resin (PAFR II) catalyst was prepared by condensation polymerization of sodium m-phenolsulfonate and paraformaldehyde in an aqueous H2SO4 solution. This reusable, robust acid resin catalyst was improved in both catalytic activity and stability, maintaining the characteristics of the previous generation catalyst (p-phenolsulfonic acid-formaldehyde resin). PAFR II was applied in the batchwise and continuous-flow direct esterification without water removal and provided higher product yields in continuous-flow esterification than any other commercial ion-exchanged acid catalyst tested.
Formal synthesis of borrelidin: A highly enantio- and diastereoselective access to the Morken's C2-C12 intermediate
Gembus, Vincent,Karmazin, Lydia,Uguen, Daniel,Zoller, Thomas
supporting information, p. 359 - 380 (2019/02/25)
In contrast to methyl and isobutyl phenyl sulfone, condensing under basic conditions higher alkyl sulfones and trans-2,3-epoxy-butanol 13c (or its O-benzyl and O-silyl derivatives) proved unfeasible, a difficulty that was overcome by using mono ethers of trans-2,3-epoxy-butane-1,4-diol 35c as the electrophilic reagents. Thus, adding excess BuLi to a mixture of the benzyl ether 35b and sulfone ent-12a, a stereodiad sulfone prepared in pure state from the R-Roche ester, via the O-trityloxy-sulfone ent-12c (X-ray), gave, after elimination by column chromatography of the side-formed regioisomer, a diolsulfone that was next converted to sulfone 20 by means of conventional functional-group modifications. Reacting like-wise this sulfone with the parent O-PMB derivative 35a, and then proceeding to the same purification process and function adjustment, delivered the title fragment in virtually pure state.