| Identification | More | [Name]
Tropinone | [CAS]
532-24-1 | [Synonyms]
(1S,5R)-8-METHYL-8-AZA-BICYCLO[3.2.1]OCTAN-3-ONE
3-TROPANONE
8-METHYL-8-AZABICYCLO[3.2.1]OCTAN-3-ONE
TIMTEC-BB SBB006924
TROPINONE
TROPIONONE
1Ah,5ah-tropan-3-one
1alphaH,5alphaH-Tropan-3-one
3-Tropinone
8-Methyl-8-azabicyclo[3.2.1]-3-octanone
N-Methyl-8-azabicyclo[3.2.1]octan-3-one
Tropanon
Tropanone
Tropinon
Tropinone,99%
Tropinone,98%
(1R,5S)-8-METHYL-8-AZABICYCLO[3.2.1]OCTAN-3-ONE
tropan-3-one
8-METHYL-8-AZABICYCLO[3,3,1OCTANE-3-ONE
8-METHYL-8-AZABICYCLO[3,2,1]OCTANE-3-ONE | [EINECS(EC#)]
208-530-6 | [Molecular Formula]
C8H13NO | [MDL Number]
MFCD00005549 | [Molecular Weight]
139.19 | [MOL File]
532-24-1.mol |
| Safety Data | Back Directory | [Hazard Codes ]
C,Xi | [Risk Statements ]
R34:Causes burns.
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S22:Do not breathe dust . | [RIDADR ]
1544 | [WGK Germany ]
3
| [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29399990 |
| Hazard Information | Back Directory | [Description]
Tropinone (8-methyl-8-azabicyclo[3.2.1]octane-3-one)(7) is the simplest plant tropane and is the first intermediate in the biosynthesis of tropane alkaloids. Studies have called 4-(1-methyl-2-pyrrolidinyl)-3-oxobutanoic acid as an intermediate metabolite in tropinone biosynthesis. | [Chemical Properties]
Tropinone is a white to light yellow crystal powder, It is an alkaloid and a precursor to a number of additional plant alkaloids. Tropinone is the first intermediate in the biosynthesis of the pharmacologically important tropane alkaloids that possesses the 8-azabicyclo[3.2.1]octane core bicyclic structure that defines this alkaloid class. Chemical synthesis of tropinone was achieved in 1901 but the mechanism of tropinone biosynthesis has remained elusive. | [Uses]
Tropinone is an oxidative product of Tropane, used to synthesize Morphine and Tropane alkaloids. | [Preparation]
The first synthesis of tropinone was by Richard Willstätter in 1901. It started from the seemingly related cycloheptanone, but required many steps and had an overall yield of only 0.75%.Willstätter had previously synthesized cocaine from tropinone, in what was the first synthesis and elucidation of the structure of cocaine.
The 1917 synthesis by Robinson is considered a legend in total synthesis due to its simplicity and biomimetic approach. 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). The synthesis is a good example of a biomimetic reaction or biogenetic-type synthesis because biosynthesis makes use of the same building blocks. It also demonstrates a tandem reaction in a one-pot synthesis. Furthermore the yield of the synthesis was 17% and with subsequent improvements exceeded 90%. | [storage]
Store at -20°C | [References]
1. Arthur J. 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. DOI:10.1098/rsnr.1993.0034
2. 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
3. Tropinone synthesis via an atypical polyketide synthase and P450-mediated cyclization DOI:10.1038/s41467-018-07671-3
4. R. Robinson (1917). "A synthesis of tropinone". Journal of the Chemical Society, Transaction 111: 762 - 768. doi:10.1039/CT9171100762 |
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