Synthon

Synthon

A synthon is a concept in retrosynthetic analysis. It is defined as a structural unit within a molecule which is related to a possible synthetic operation. The term was coined by E.J. Corey. It is noted [Organic Synthesis, the science behind the art. W.A. Smit, A.F. Buchkov, R.Cople, Royal Society of Chemistry ISBN 0-85404-544-9 ] that the phrase does not feature very prominently in Corey's book, "The Logic of Chemical Synthesis", as it is not included in the index.

Example

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 per se; synthetic equivalents corresponding to the synthons are reacted to produce the desired product. 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:

# PhCH2Br + NaCN → PhCH2CN + NaBr
# PhCH2CN + 2 H2O → PhCH2COOH + NH3

Common synthons

* C1 synthons - carbon dioxide, carbon monoxide, cyanide
* C2 synthons - acetylene, acetaldehyde
* -C2H4OH synthon - ethylene oxide
* carbocation synthons - alkyl halides
* carbanion synthons - Grignard reagents, organolithiums, substituted acetylides

References


Wikimedia Foundation. 2010.

Игры ⚽ Поможем сделать НИР

Look at other dictionaries:

  • synthon — /sinˈthon/ (chem) noun (within a molecule to be synthesized) a constituent part which can be readily used in the synthesis process ORIGIN: synthetic and ion …   Useful english dictionary

  • Synthon — Ein Synthon ist ein konzeptioneller Baustein der Retrosynthese Planung und wurde von E. J. Corey entwickelt.[1] Inhaltsverzeichnis 1 Herleitung 2 Beispiel 3 Beispiele für Synthone …   Deutsch Wikipedia

  • Synthon — Un synthon est une molécule fictive dont la représentation symbolise la réactivité. Ainsi, le synthon R+ peut réagir avec le synthon R pour former la molécule R R . Les synthons n existent pas, et il faut leur trouver des équivalents synthétiques …   Wikipédia en Français

  • synthon — noun In retrosynthetic analysis, a structural unit within a molecule which is related to a possible synthetic operation …   Wiktionary

  • Synthon — Syn|thon [zu ↑ Synthese], das; s, s u. e: im ursprünglichen Sinn eine Bez. aus der retrosynthetischen Analyse für eine Schlüsselstruktur in einem Molekül, für die geeignete Synthesemöglichkeiten gefunden werden müssen (↑ Retron). Für chirale S.… …   Universal-Lexikon

  • Retrosynthese — Die Retrosynthese oder auch retrosynthetische Analyse ist eine Technik beim Planen einer chemischen Synthese von komplexen organischen Molekülen. Dabei wird das Molekül gedanklich in einfachere Bausteine zerlegt, für deren Verknüpfung… …   Deutsch Wikipedia

  • Crystal engineering — An example of crystal engineering using hydrogen bonding reported by Wuest and coworkers in J. Am. Chem. Soc., 2007, 4306–4322. Crystal engineering is the design and synthesis of molecular solid state structures with desired properties, based on… …   Wikipedia

  • Retrosynthetic analysis — is a technique for solving problems in the planning of organic syntheses. This is achieved by transforming a target molecule into simpler precursor structures without assumptions regarding starting materials. Each precursor material is examined… …   Wikipedia

  • Zinkdiethyl — Strukturformel Allgemeines Name Diethylzink Andere Namen Zinkdiethyl DEZ …   Deutsch Wikipedia

  • Cyanide — This article is about the class of chemical compounds. For other uses, see Cyanide (disambiguation). The cyanide ion, CN−. From the top: 1. Valence bond structure 2. Space filling model 3. Electrostatic potential surface 4. Carbon lone pair… …   Wikipedia

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”