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![1,5-Diazabicyclo[4.3.0]non-5-ene (CAS 3001-72-7) - chemical structure image](https://media.scbt.com/product/1-5-diazabicyclo4-3-0non-5-ene-3001-72-7-structure_10_64_t_106491.jpg "Molecular structure of 1,5-Diazabicyclo[4.3.0]non-5-ene, CAS Number: 3001-72-7")
1,5-Diazabicyclo[4.3.0]non-5-ene (CAS 3001-72-7)
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1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) is a bicyclic organic compound featuring a unique structure that comprises a nine-membered ring fused with two nitrogen atoms at the 1 and 5 positions. This configuration imparts 1,5-Diazabicyclo[4.3.0]non-5-ene with distinctive nucleophilic properties, making it an invaluable catalyst in organic synthesis. Its mechanism of action primarily involves serving as an organocatalyst, facilitating a range of chemical reactions, including but not limited to Michael additions, Aldol reactions, and the activation of carbonyl compounds. In research, 1,5-Diazabicyclo[4.3.0]non-5-ene′s efficacy in promoting carbon-carbon bond formation under mild conditions has been extensively utilized, enabling the synthesis of complex molecules with high specificity and yield. The compound′s robustness and versatility in catalyzing reactions have made it a staple in the development of new synthetic methodologies, contributing significantly to the field of green chemistry by offering more sustainable and environmentally friendly alternatives to traditional catalytic processes.
1,5-Diazabicyclo[4.3.0]non-5-ene (CAS 3001-72-7) References
- Friedel-Crafts acylation of pyrroles and indoles using 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) as a nucleophilic catalyst. | Taylor, JE., et al. 2010. Org Lett. 12: 5740-3. PMID: 21077631
- The vaporization enthalpies of 2- and 4-(N,N-dimethylamino)pyridine, 1,5-diazabicyclo[4.3.0]non-5-ene, 1,8-diazabicyclo[5.4.0]undec-7-ene, imidazo[1,2-a]pyridine and 1,2,4-triazolo[1,5-a]pyrimidine by correlation-gas chromatography. | Lipkind, D., et al. 2011. J Phys Chem B. 115: 8785-96. PMID: 21648413
- 1,1/1,2 Isomerisation in Lewis base adducts of B2cat2. | Cade, IA., et al. 2015. Dalton Trans. 44: 7506-11. PMID: 25803123
- Ionic liquid mediated technology for synthesis of cellulose acetates using different co-solvents. | Jogunola, O., et al. 2016. Carbohydr Polym. 135: 341-8. PMID: 26453886
- Direct Aminolysis of Ethoxycarbonylmethyl 1,4-Dihydropyridine-3-carboxylates. | Vigante, B., et al. 2015. Molecules. 20: 20341-54. PMID: 26569215
- p-Nitrophenyl carbonate promoted ring-opening reactions of DBU and DBN affording lactam carbamates. | Vangala, M. and Shinde, GP. 2016. Beilstein J Org Chem. 12: 2086-2092. PMID: 27829914
- Vaporization of protic ionic liquids derived from organic superbases and short carboxylic acids. | Ribeiro, FMS., et al. 2017. Phys Chem Chem Phys. 19: 16693-16701. PMID: 28621368
- Enantioselective 1,3-Dipolar Cycloaddition of Methyleneindolinones with α-Diazomethylphosphonate to Access Chiral Spiro-phosphonylpyrazoline-oxindoles Catalyzed by Tertiary Amine Thiourea and 1,5-Diazabicyclo[4.3.0]non-5-ene. | Huang, N., et al. 2017. Org Lett. 19: 5806-5809. PMID: 29045154
- Experimental Evidence for Azeotrope Formation from Protic Ionic Liquids. | Ribeiro, FMS., et al. 2018. Chemphyschem. 19: 2364-2369. PMID: 29799151
- Solvent Welding and Imprinting Cellulose Nanofiber Films Using Ionic Liquids. | Reyes, G., et al. 2019. Biomacromolecules. 20: 502-514. PMID: 30540441
- CuII -Catalyzed Oxidative Formation of 5-Alkynyltriazoles. | Liu, P., et al. 2020. Chem Asian J. 15: 380-390. PMID: 31845533
- Recyclable Organocatalyzed Poly(Thiourethane) Covalent Adaptable Networks. | Gamardella, F., et al. 2020. Polymers (Basel). 12: PMID: 33291704
- Selective N-Arylation of p-Aminophenylalanine in Unprotected Peptides with Organometallic Palladium Reagents. | Mallek, AJ., et al. 2021. Angew Chem Int Ed Engl. 60: 16928-16931. PMID: 34015170
- Robust superbase-based emerging solvents for highly efficient dissolution of cellulose. | Liu, Q., et al. 2021. Carbohydr Polym. 272: 118454. PMID: 34420714
- Sensing Techniques for Organochlorides through Intermolecular Interaction with Bicyclic Amidines. | Park, JW., et al. 2021. Biosensors (Basel). 11: PMID: 34821631
Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
1,5-Diazabicyclo[4.3.0]non-5-ene, 5 g | sc-237778 | 5 g | $40.00 | |||
1,5-Diazabicyclo[4.3.0]non-5-ene, 25 g | sc-237778A | 25 g | $98.00 |