In retrosynthetic analysis, a synthon is a hypothetical unit within a target molecule that represents a potential starting reagent in the retroactive synthesis of that target molecule. The term was coined in 1967 by E. J. Corey. He noted in 1988 that the "word synthon has now come to be used to mean synthetic building block rather than retrosynthetic fragmentation structures".
It was noted in 1998 that the phrase did not feature very prominently in Corey's 1981 book The Logic of Chemical Synthesis, as it was not included in the index. Because synthons are charged, when placed into a synthesis an uncharged form is found commercially instead of forming and using the potentially very unstable charged synthons.
In planning the synthesis of phenylacetic acid, two synthons are identified: a nucleophilic "COOH−" group, and an electrophilic "PhCH2+" group. Of course, both synthons do not exist by themselves; synthetic equivalents corresponding to the synthons are reacted to produce the desired reactant. In this case, the cyanide anion is the synthetic equivalent for the COOH− synthon, while benzyl bromide is the synthetic equivalent for the benzyl synthon.
The synthesis of phenylacetic acid determined by retrosynthetic analysis is thus:
where Ph stands for phenyl.
C2 synthons - acetylene, acetaldehyde
C2H4OH synthon - ethylene oxide
carbocation synthons - alkyl halides
carbanion synthons - Grignard reagents, organolithiums, substituted acetylides
This term is also used in the field of gene synthesis—for example "40-base synthetic oligonucleotides are built into 500- to 800-bp synthons".
In 1967, E. J. Corey introduced the concept of a synthon in retrosynthetic analysis. Planning the steps of a complex molecule synthesis requires recognizing key synthons and identifying how they can be assembled into a desired product. In many retrosynthetic bond disconnections, the bond is broken heterolytically instead of homolytically, generating a carbocationtic and a carbanionic synthon.
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Un synthon est une « molécule fictive » dont la représentation symbolise la réactivité. Ce concept est utilisé dans la planification de rétrosynthèses de composés organiques complexes. Ils sont dérivés d'une décomposition en fragments simples de la molécule que l'on cherche à assembler. Plus récemment et par extension, on désigne fréquemment par le terme synthon des éléments ou briques de base utilisés en synthèse organique.
Les réactifs de Grignard, également appelés organomagnésiens mixtes, sont une classe de composés chimiques couramment utilisés en synthèse organique, notamment en chimie fine, comme dans l'industrie pharmaceutique. Ce sont des halogénures organomagnésiens de formule générique RMgX, où R représente un résidu organique, généralement alkyle ou aryle, et X représente un halogène, en général le brome ou le chlore, parfois l'iode et exceptionnellement le fluor.
In organic chemistry, a carbanion is an anion in which carbon is negatively charged. Formally, a carbanion is the conjugate base of a carbon acid: where B stands for the base. The carbanions formed from deprotonation of alkanes (at an sp3 carbon), alkenes (at an sp2 carbon), arenes (at an sp2 carbon), and alkynes (at an sp carbon) are known as alkyl, alkenyl (vinyl), aryl, and alkynyl (acetylide) anions, respectively.