22117-49-3Relevant academic research and scientific papers
Exploring the synthetic potential of a marine transaminase including discrimination at a remote stereocentre
Schwarz, Maria,Murphy, Edel J.,Foley, Aoife M.,Woods, David F.,Castilla, Ignacio Abreu,Reen, F. Jerry,Collins, Stuart G.,O'gara, Fergal,Maguire, Anita R.
supporting information, p. 188 - 198 (2021/01/18)
The marine transaminase, P-ω-TA, can be employed for the transamination from 1-aminotetralins and 1-aminoindanes with differentiation of stereochemistry at both the site of reaction and at a remote stereocentre resulting in formation of ketone products with up to 93% ee. While 4-substituents are tolerated on the tetralin core, the presence of 3- or 8-substituents is not tolerated by the transaminase. In general P-ω-TA shows capacity for remote diastereoselectivity, although both the stereoselectivity and efficiency are dependent on the specific substrate structure. Optimum efficiency and selectivity are seen with 4-haloaryl-1-aminotetralins and 3-haloaryl-1-aminoindanes, which may be associated with the marine origin of this enzyme. This journal is
1,2,3,4-Tetrahydronaphthalene compound and preparation method and application thereof
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Paragraph 0140; 0193; 0195; 0196, (2018/12/03)
The invention discloses 1,2,3,4-tetrahydronaphthalene compound and a preparation method and application thereof. The 1,2,3,4-tetrahydronaphthalene compound has a molecular structural formula shown asformula (I) that is shown in the description. The prepar
Visible-Light-Mediated [4+2] Cycloaddition of Styrenes: Synthesis of Tetralin Derivatives
Wang, Leifeng,Wu, Fengjin,Chen, Jiean,Nicewicz, David A.,Huang, Yong
supporting information, p. 6896 - 6900 (2017/06/08)
We report a formal [4+2] cycloaddition reaction of styrenes under visible-light catalysis. Two styrene molecules with different electronic or steric properties were found to react with each other in good yield and excellent chemo- and regioselectivity. This reaction provides direct access to polysubstituted tetralin scaffolds from readily available styrenes. Sophisticated tricyclic and tetracyclic tetralin analogues were prepared in high yield and up to 20/1 diasteroselectivity from cyclic substrates.
Synthesis of 1-aryl-tetralins and 4-aryl-benzopyrans by sulfoxide-mediated benzylic carbocation cyclizations
Volonterio, Alessandro,Zanda, Matteo
, p. 8723 - 8726 (2007/10/03)
An alkylation/cyclization sequence, with both steps mediated by the ortho-N-methylformamido-phenylsulfinyl function, provided two new C-C bonds and an efficient entry to 1-aryl-tetralins and 4-aryl-benzopyrans. Scope and limits of the process have been studied in detail.
Anomalous Acetoxylation of Aromatic Nuclei: Some Structural Requirements in the Substrate
Bandaranayake, Wickramasinghe M.,Riggs, Noel V.
, p. 115 - 129 (2007/10/02)
For certain aromatic nuclei, bromination in acetic acid in the presence of pyridine is accompanied by nuclear acetoxylation.As first observed with galbulin, when two alkoxyl groups, one meta and one para to a benzylic centre of the substrate are present, acetoxylation occurs at the intervening ortho position.Under the given conditions, acetoxylation occurs at position 8 of 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydronaphthalene, and at position 2 of 3,4-dimethoxy diphenyl and triphenyl-methanes.Acetoxylation does not occur in the absence of either of the alkoxy groups or in the absence of pyridine, not does it occur in the pendant ring of 1-(3',4'-dimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene.These results are consistent with the earlier suggestion that the reaction occurs by way of initial oxidative formation of a doubly benzylic cation
