| Tropinone | |
|---|---|
 |  |
| IUPAC name | 8-Methyl-8-azabicyclo[3. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general 2. 1]octan-3-one |
| Other names | 3-Tropinone |
| Identifiers | |
| CAS number | [532-24-1] |
| PubChem | |
| SMILES | O=C1CC2N(C)C(CC2)C1 |
| Properties | |
| Molecular formula | C8H13NO |
| Molar mass | 139. CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 195 g/mol |
| Appearance | Brown solid |
| Melting point | 42. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. 5 °C, 316 K, 109 °F |
| Boiling point | (decomposes) |
| Hazards | |
| NFPA 704 |  1 2 0 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
Tropinone is an alkaloid, famously synthesised in 1917 by Robert Robinson as a synthetic precursor to atropine, a scarce commodity during World War I. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid Symbolism The four divisions are typically color-coded with blue indicating level of Health Hazard, red indicating In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly This article is about the chemical compounds alkaloids For the Pharmaceutical company in the Republic of Macedonia see Alkaloid (company. Sir Robert Robinson OM, PRS ( 13 September 1886 – 8 February 1975) was an English chemist and Nobel laureate Organic chemistry is a discipline within Chemistry which involves the scientific study of the structure properties composition reactions, and preparation Atropine is a Tropane Alkaloid extracted from Deadly nightshade ( Atropa belladonna) Jimsonweed (Datura stramonium and other plants World War I (abbreviated WWI; also known as the First World War, the Great War, and the War to End All [1][2] Tropinone and the alkaloids cocaine and atropine all share the same tropane core structure. Cocaine ( benzoylmethyl ecgonine) is a Crystalline Tropane Alkaloid that is obtained from the leaves of the Coca plant Tropane is a Nitrogenous Bicyclic Organic compound. It is mainly known for a group of Alkaloids derived from it (called Tropane alkaloids
Contents |
Synthesis
The first synthesis of tropinone was by Richard Willstätter in 1901. Richard Martin Willstätter ( August 13, 1872 – August 3, 1942) was a German Organic chemist whose study of the structure It started from the seemingly related cycloheptanone, but required many steps and had an overall yield of only 0. 75%. [3] Willstätter had previously synthesized cocaine from tropinone, in what was the first synthesis and elucidation of the structure of cocaine. [4]
The 1917 synthesis by Robinson is considered a legend in total synthesis[5] due to its simplicity and biomimetic approach. In principle a total synthesis is the complete Chemical synthesis of complex organic Molecules from simpler pieces usually without the aid of biological Tropinone is a bicyclic molecule, but the reactants used in its preparation are fairly simple: succinaldehyde, methyl amine and acetone dicarboxylic acid (or even acetone). bicyclic molecule contains two fused Aliphatic rings. Fusion can occur in three ways At two mutually bonded atoms or Across a sequence of atoms A reagent or reactant is a substance or compound consumed during a Chemical reaction. Methylamine is the Chemical compound with a formula of CH3NH2 Acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is a colorless mobile flammable The synthesis is a good example of a biomimetic reaction or biogenetic-type synthesis because biosynthesis makes use of the same building blocks. Bionics (also known as biomimetics, biognosis, Biomimicry, or bionical creativity engineering) is the application of biological Biosynthesis is a phenomenon wherein Chemical compounds are produced from simpler Reagents Biosynthesis unlike Chemosynthesis, takes place within living It also demonstrates a tandem reaction in a one-pot synthesis. A cascade reaction or tandem reaction or domino reaction is a consecutive series of Intramolecular Organic reactions which often proceed via highly In Chemistry a one-pot synthesis is a strategy to improve the efficiency of a Chemical reaction whereby a Reactant is subjected to successive chemical reactions Furthermore the yield of the synthesis was 17% and with subsequent improvements exceeded 90%. [3]
Reaction mechanism
The main features apparent from the reaction sequence below are:
- Nucleophilic addition of secondary amine to aldehyde followed by loss of water to create an imine
- Nucleophilic addition of the imine to the second aldehyde unit and first ring closure
- Intermolecular Mannich reaction of the enolate of actone dicarboxylate
- New enolate formation and new imine formation with loss of water for
- Second intramolecular mannich reaction and second ring closure
- Loss of 2 carboxylic groups to tropinone
References
- ^ R. In Organic chemistry, a nucleophilic addition reaction is an Addition reaction where in a Chemical compound a π bond is removed by the creation Amines are Organic compounds and Functional groups that contain a basic Nitrogen Atom with a Lone pair. An aldehyde is an organic compound containing a terminal Carbonyl group. An imine is a Functional group or Chemical compound containing a Carbon – Nitrogen Double bond. In Physics, Chemistry, and Biology, intermolecular forces are forces that act between stable Molecules or between functional groups of The Mannich reaction is an Organic reaction which consists of an amino alkylation of an acidic proton placed next to a Carbonyl Functional group Enols (also known as alkenols) are Alkenes with a Hydroxyl group affixed to one of the carbon atoms composing the Double bond. Intramolecular in Chemistry describes a process or characteristic limited within the structure of a single Molecule; a property or phenomenon limited to the extent Robinson (1917). "A synthesis of tropinone". Journal of the Chemical Society, Transaction 111: 762 - 768. The Journal of the Chemical Society was a Scientific journal published from 1862 to 1877 and from 1926 to 1965 by the Chemical Society which merged with other doi:. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.
- ^ The Art and Science of Total Synthesis at the Dawn of the Twenty-First Century K. C. Nicolaou, Dionisios Vourloumis, Nicolas Winssinger, and Phil S. Baran Angew. Chem. Int. Ed. 2000, 39, 44 ± 122
- ^ a b Smit, W. et al. (1998) Organic Synthesis, The Science behind the Art. Cambridge: The Royal Society of Chemistry.
- ^ Andrew J. Humphrey and David O'Hagan. Tropane alkaloid biosynthesis. A century old problem unresolved. Natural Products Reports 2001, 18, 494-502. doi:10.1039/b001713m
- ^ Arthur J. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. Birch. Investigating a Scientific Legend: The Tropinone Synthesis of Sir Robert Robinson, F. R. S. Notes and Records of the Royal Society of London, 1993, 47, 277-296.
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