532-24-1 Usage
Description
Tropinone is an alkaloid and a precursor to a number of additional plant alkaloids, including the pharmacologically important tropane alkaloids. It is an oxidative product of Tropane and possesses the 8-azabicyclo[3.2.1]octane core bicyclic structure that defines this alkaloid class. Tropinone is a white to light yellow crystal powder and was first synthesized chemically in 1901.
Uses
Used in Pharmaceutical Industry:
Tropinone is used as a key intermediate for the synthesis of Morphine and other Tropane alkaloids, which are essential in the development of various pharmaceutical products. These alkaloids have significant applications in medicine due to their analgesic, sedative, and stimulant properties.
Used in Chemical Synthesis:
Tropinone serves as a crucial starting material in the chemical synthesis of a wide range of tropane alkaloids, which are known for their diverse biological activities and potential therapeutic applications. The synthesis of tropinone allows for the exploration and development of new compounds with improved pharmacological properties and reduced side effects.
Preparation
The first synthesis of tropinone was by Richard Willst?tter in 1901. It started from the seemingly related cycloheptanone, but required many steps and had an overall yield of only 0.75%.Willst?tter 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%.
Check Digit Verification of cas no
The CAS Registry Mumber 532-24-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 2 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 532-24:
(5*5)+(4*3)+(3*2)+(2*2)+(1*4)=51
51 % 10 = 1
So 532-24-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H13NO/c1-9-6-2-3-7(9)5-8(10)4-6/h6-7H,2-5H2,1H3/p+1/t6-,7+
532-24-1Relevant articles and documents
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Polievktov et al.
, (1975)
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Bioactivity-guided synthesis of tropine derivatives as new agonists for melatonin receptors
Yin, Xiu-Juan,Geng, Chang-An,Huang, Xiao-Yan,Chen, Hao,Ma, Yun-Bao,Chen, Xing-Long,Sun, Chang-Li,Yang, Tong-Hua,Zhou, Jun,Zhang, Xue-Mei,Chen, Ji-Jun
, p. 45059 - 45063 (2016)
Twenty-three tropine derivatives as new melatonin receptor (MT1 and MT2) agonists were synthesized and evaluated on HEK293 cells in vitro. Derivatives 1f, 1i, 1j, 1m-1s and 1t exhibited increased agonisting activities on MT1 and MT2 receptors compared to the substrate tropine. Particularly, compound 1r showed significant agonistic activities on MT1 and MT2 receptors with EC50 values of 0.20 and 0.24 mM, respectively. The preliminary structure-activity relationships (SARs) of tropine derivatives were summarized for further investigation on melatonin receptor agonists.
METHOD OF PRODUCING TERTIARY AMINE OR TERTIARY AMINE DERIVATIVE
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Paragraph 0066; 0073; 0079, (2018/10/31)
PROBLEM TO BE SOLVED: To provide a method of producing tertiary amine or tertiary amine derivative with high selectivity. SOLUTION: In the method of producing tertiary amine or tertiary amine derivative, a reaction system including: an organic chemical raw material containing at least one kind of group selected from -NH2, -NH2 HCl, >NH and >NH HCl, a nitrogen atom contained in the group bounding to a carbon atom; aliphatic alcohol having 1 to 20 carbon atoms; and a catalyst where a carrier containing titanium oxide carries a silver component (metal silver or silver compound), is irradiated with light, and the group in the organic compound raw material is converted to -NR02 or >NR0, ( R0 is an aliphatic hydrocarbon group having 1 to 20 carbon atoms derived from the aliphatic alcohol). The percentage content of the silver in the catalyst is 0.5 to 10 mass% with respect to the titanium oxide. COPYRIGHT: (C)2015,JPOandINPIT
A facile synthesis of enantiopure 7-benzyloxycarbonyl-7-azabicyclo [2.2.1]heptane-2-carboxylic acid
Chiou, Wen-Hua,Chiang, Yu-Min,Chen, Guei-Tang
, p. 92 - 97 (2014/02/14)
An efficient procedure for the preparation of enantiopure 7-benzyloxycarbonyl-7-azabicyclo[2.2.1]heptane-2-carboxylic acids is described.