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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (or DDQ) is the chemical reagent with formula C 6 Cl 2 (CN) 2 O 2. This oxidant is useful for the dehydrogenation of alcohols, [3] phenols, [4] and steroid ketones. [5] DDQ decomposes in water, but is stable in aqueous mineral acid. [6]
Orthogonal protection is a strategy allowing the specific deprotection of one protective group in a multiply-protected structure. For example, the amino acid tyrosine could be protected as a benzyl ester on the carboxyl group, a fluorenylmethylenoxy carbamate on the amine group, and a tert-butyl ether on the phenol
It is also a good test for the successful deprotection of a secondary amine. Secondary amines react with chloranil to give a brown/red/orange derivative, the colour depending on the amine. In these reactions, the amine displaces chloride from the ring of the quinone.
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Trichloroethyl chloroformate is used in organic synthesis for the introduction of the trichloroethyl chloroformate (Troc) protecting group for amines, thiols and alcohols.It readily cleaves vs other carbamates and can be used in an overall protecting group strategy.
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) is often the reagent of choice. DDQ and an acid catalyst has been used to synthesise a steroid with a phenanthrene core by oxidation accompanied by a double methyl migration. [9] In the process, DDQ is itself reduced into an aromatic hydroquinone product.
As a second example, researchers synthesized a cycloprene-modified glutamate photocaged with a 2-nitroveratrol-based PPG. As it is an excitatory amino acid neurotransmitter, the aim was to develop a bioorthagonal probe for glutamate in vivo. [47] In a final example, Venkatesh et al. demonstrated the use of a PPG-based photocaged therapeutic. [48]
1,4-Benzoquinone, commonly known as para-quinone, is a chemical compound with the formula C 6 H 4 O 2.In a pure state, it forms bright-yellow crystals with a characteristic irritating odor, resembling that of chlorine, bleach, and hot plastic or formaldehyde.