Chemistry:Cyclopropylamine
From HandWiki
Cyclopropylamine is the organic compound with the formula C
3H
5NH
2. It is a simple amine derivative of cyclopropane.[1] As a precursor to pesticides and pharmaceuticals, it is produced on a multi-ton scale from the carboxamide.[2] Cycloproylamine is first member of the aminocycloalkanes, which includes cyclobutylamine, cyclopentylamine, and cyclohexylamine.
Cyclopropylamines
Many aminocyclopropanes are known, most prominently the amino acid aminocyclopropane-1-carboxylic acid.
The cyclopropylamine group is featured in several pharmaceutical drugs:[2]
- Simeprevir, used to treat hepatitis C infections
- Risdiplam, used to treat spinal muscular atrophy
- ciprofloxacin, an antibiotic.
Cyclopropylamines can be prepared by the Kulinkovich reaction, by dialkylation of bromonitromethane, and various cyclopropanations.[3][4]
References
- ↑ Bertus, Philippe; Caillé, Julien (2025). "Advances in the Synthesis of Cyclopropylamines". Chemical Reviews 125 (6): 3242–3377. doi:10.1021/acs.chemrev.4c00674. PMID 40048498.
- ↑ 2.0 2.1 Huang, Jinpei; Geng, Yuhao; Wang, Yundong; Xu, Jianhong (2019). "Efficient Production of Cyclopropylamine by a Continuous-Flow Microreaction System". Industrial & Engineering Chemistry Research 58 (36): 16389–16394. doi:10.1021/acs.iecr.9b02438.
- ↑ Cha, Jin Kun; Kulinkovich, Oleg G. (2012). "The Kulinkovich Cyclopropanation of Carboxylic Acid Derivatives". Organic Reactions. pp. 1–160. doi:10.1002/0471264180.or077.01. ISBN 978-0-471-26418-7.
- ↑ Sokolova, Olga O.; Bower, John F. (2021). "Selective Carbon–Carbon Bond Cleavage of Cyclopropylamine Derivatives". Chemical Reviews 121 (1): 80–109. doi:10.1021/acs.chemrev.0c00166. PMID 32567848. https://livrepository.liverpool.ac.uk/3117450/1/Cyclopropylamine%20Chem%20Rev%20Revised%20version%204%20no%20highlights.pdf.
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