Dioxepin
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| Category | Others |
| Catalog number | BBF-05379 |
| CAS | 39372-88-8 |
| Molecular Weight | 98.10 |
| Molecular Formula | C5H6O2 |
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Specification
| Synonyms | Dioxepine; 3H-dioxepine |
| IUPAC Name | 3H-1,2-dioxepine |
| Canonical SMILES | C1C=CC=COO1 |
| InChI | InChI=1S/C5H6O2/c1-2-4-6-7-5-3-1/h1-4H,5H2 |
| InChI Key | JOWXBGIZDALBJW-UHFFFAOYSA-N |
Reference Reading
1. Molecular Basis for Spirocycle Formation in the Paraherquamide Biosynthetic Pathway
Amy E Fraley, Kersti Caddell Haatveit, Ying Ye, Samantha P Kelly, Sean A Newmister, Fengan Yu, Robert M Williams, Janet L Smith, K N Houk, David H Sherman J Am Chem Soc. 2020 Feb 5;142(5):2244-2252. doi: 10.1021/jacs.9b09070. Epub 2020 Jan 16.
The paraherquamides are potent anthelmintic natural products with complex heptacyclic scaffolds. One key feature of these molecules is the spiro-oxindole moiety that lends a strained three-dimensional architecture to these structures. The flavin monooxygenase PhqK was found to catalyze spirocycle formation through two parallel pathways in the biosynthesis of paraherquamides A and G. Two new paraherquamides (K and L) were isolated from a ΔphqK strain of Penicillium simplicissimum, and subsequent enzymatic reactions with these compounds generated two additional metabolites, paraherquamides M and N. Crystal structures of PhqK in complex with various substrates provided a foundation for mechanistic analyses and computational studies. While it is evident that PhqK can react with various substrates, reaction kinetics and molecular dynamics simulations indicated that the dioxepin-containing paraherquamide L is the favored substrate. Through this effort, we have elucidated a key step in the biosynthesis of the paraherquamides and provided a rationale for the selective spirocyclization of these powerful anthelmintic agents.
2. Investigations into the biosynthesis of the antifungal strobilurins
Zafar Iqbal, Li-Chen Han, Anna M Soares-Sello, Risa Nofiani, Gerald Thormann, Axel Zeeck, Russell J Cox, Christine L Willis, Thomas J Simpson Org Biomol Chem. 2018 Aug 1;16(30):5524-5532. doi: 10.1039/c8ob00608c.
The strobilurins are important antifungal metabolites isolated from a number of basidiomycetes and have been valuable leads for the development of commercially important fungicides. Isotopic labelling studies with early and advanced intermediates confirm for the first time that they are produced via a linear tetraketide, primed with the rare benzoate starter unit, itself derived from phenylalanine via cinnamate. Isolation of a novel biphenyl metabolite, pseudostrobilurin B, provides evidence for the involvement of an epoxide in the key rearrangement to form the β-methoxyacrylate moiety essential for biological activity. Formation of two bolineol related metabolites, strobilurins Y and Z, also probably involves epoxide intermediates. Time course studies indicate a likely biosynthetic pathway from strobilurin A, with the simplest non-subsubstituted benzoate ring, to strobilurin G with a complex dioxepin terpenoid-derived substituent. Precursor-directed biosynthetic studies allow production of a number of novel ring-halogenated analogues as well as a new pyridyl strobilurin. These studies also provide evidence for a non-linear biosynthetic relationship between strobilurin A and strobilurin B.
3. Total Synthesis of ( S)-Cularine via Nucleophilic Substitution on a Catechol
Zheng Huang, Xiang Ji, Jean-Philip Lumb Org Lett. 2021 Jan 1;23(1):236-241. doi: 10.1021/acs.orglett.0c04000. Epub 2020 Dec 16.
Catechols are part of many essential chemicals and are valuable, typically nucleophilic intermediates used in synthesis. Here we describe an unexpected transformation in which they play the role of the electrophile in a formal nucleophilic aromatic substitution. We made this discovery while studying a seven-membered dioxepin ring formation during a synthesis of the benzyltetrahydroisoquinoline (S)-cularine. We suggest a chain mechanism for this new transformation that is triggered by molecular oxygen and that propagates an electrophilic ortho-quinone.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
