Ortho esters
Ortho esters are a class of compounds characterized by the presence of an ester group attached to a hydroxyl group on the same carbon atom, forming a four-membered cyclic structure. Structurally, ortho esters can be represented as R-C(O)-O-R', where R and R' represent alkyl or aryl groups, with R and O directly bonded to each other, creating the unique ortho-ester linkage.
These compounds are of significant interest in chemical synthesis due to their potential reactivity. Unlike traditional esters that undergo hydrolysis readily under basic conditions, ortho esters exhibit enhanced stability, which can be leveraged for controlled release applications or as protective groups in organic synthesis. The substitution pattern allows these molecules to form cyclic structures, offering distinct steric and electronic effects compared to other esters.
In various applications, ortho esters find use in pharmaceuticals, materials science, and polymer chemistry. Their ability to undergo hydrolysis under specific conditions makes them valuable as prodrugs or for the modification of surfaces through controlled release mechanisms.
| Structure | Chemical Name | CAS | MF |
|---|---|---|---|
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2-Methoxy-1,3-dioxolane | 19693-75-5 | C4H8O3 |
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1,1,1-Trimethoxybutane | 43083-12-1 | C7H16O3 |
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Trimethyl orthopropionate | 24823-81-2 | C6H14O3 |
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Tripropoxymethane | 621-76-1 | C10H22O3 |
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Tetramethoxymethane | 1850-14-2 | C5H12O4 |
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2-Methoxy-2-methyl-1,3-dioxolane | 19798-71-1 | C5H10O3 |
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1,4,6-Trioxaspiro[4.4]nonane, 2-methyl-7-methylene- | 105632-19-7 | C8H12O3 |
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Cyclohexane,(1,1-dimethoxyethoxy)- | 55844-53-6 | C10H20O3 |
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tris(2,2,2-trifluoroethyl)orthoformate | 58244-27-2 | C7H7F9O3 |
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Triethyl Orthoacetate-d3 | 97419-13-1 | C8H18O3 |
Related Literature
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Gaurav J. Shah,Eric P.-Y. Chiou,Ming C. Wu,Chang-Jin “CJ” Kim Lab Chip, 2009,9, 1732-1739
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Weili Dai,Guangjun Wu,Michael Hunger Chem. Commun., 2015,51, 13779-13782
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Joseph W. Bennett,Diamond T. Jones,Blake G. Hudson,Joshua Melendez-Rivera,Robert J. Hamers,Sara E. Mason Environ. Sci.: Nano, 2020,7, 1642-1651
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J. Xu,T. J. Carrocci,A. A. Hoskins Chem. Commun., 2016,52, 549-552
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Brindha J.,Balamurali M. M.,Kaushik Chanda RSC Adv., 2019,9, 34720-34734
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