2382-08-3Relevant articles and documents
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Devereux,Donahoe
, p. 457 (1960)
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Photoinduced cycloadditions of N-methyl-1,8-naphthalenedicarboximides with alkynes
Liu, Qing-Jian,Shen, Yong-Miao,An, Hui-Ying,Grampp, Günter,Landgraf, Stephan,Xu, Jian-Hua
, p. 1131 - 1138 (2006)
Photoinduced cycloadditions of N-methyl-1,8-naphthalenedicarboximide 1 with phenylacetylenes 2a-2c, cyclopropylacetylene 2d, diphenylacetylenes 2e-2f and 1-phenylpropyne 2g were investigated. In the case of phenylacetylenes 2a, 2b and cyclopropylacetylene 2c, photoreaction with 1 takes place at the naphthalene C(1)C(2) bond to give the cyclobutene products. For 4-methoxyphenylacetylene 1c, the cyclobutene 3c is obtained together with the 4-benzo[a]thebenidinone 4c derived from a primary oxetene product formed by [2+2] addition of the imide carbonyl with the alkyne. Similar to 2c, photocycloaddition of 1 with 2e and 2f gave the cyclobutenes 7e, 7f, 8f and the 4-benzo[a]thebenidinone products 9e, 9f and 10f, respectively, derived from the corresponding oxetenes. Photoreaction of 1 with 2g gave cyclobutene 7g and benzo[a]thebenidinone 9g. Sensitization experiment and internal heavy atom effect study showed that these reactions proceed from the ππ* singlet excited state of 1. Estimation of the free energy change for electron transfer between 11* and the alkynes and the calculation of charge and spin density distribution in the anion radical of 1 and the cation radical of the alkynes suggested that the cyclobutene products are formed by direct [2+2] cycloaddition of 11* with the alkyne, while the formation of the oxetene products is the result of electron transfer interaction between 11* and the alkyne. The regioselectivity in the oxetene formation is accounted for by charge and spin density distribution in the anion radical of 1 and the cation radical of the alkyne.
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Amith,Ginsburg
, p. 1819,1820,1823 (1973)
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Target Enzyme-Activated Two-Photon Fluorescent Probes: A Case Study of CYP3A4 Using a Two-Dimensional Design Strategy
Ning, Jing,Wang, Wei,Ge, Guangbo,Chu, Peng,Long, Feida,Yang, Yongliang,Peng, Yulin,Feng, Lei,Ma, Xiaochi,James, Tony D.
, p. 9959 - 9963 (2019)
The rapid development of fluorescent probes for monitoring target enzymes is still a great challenge owing to the lack of efficient ways to optimize a specific fluorophore. Herein, a practical two-dimensional strategy was designed for the development of an isoform-specific probe for CYP3A4, a key cytochrome P450 isoform responsible for the oxidation of most clinical drugs. In first dimension of the design strategy, a potential two-photon fluorescent substrate (NN) for CYP3A4 was effectively selected using ensemble-based virtual screening. In the second dimension, various substituent groups were introduced into NN to optimize the isoform-selectivity and reactivity. Finally, with ideal selectivity and sensitivity, NEN was successfully applied to the real-time detection of CYP3A4 in living cells and zebrafish. These findings suggested that our strategy is practical for developing an isoform-specific probe for a target enzyme.
Isoindolinone Synthesis: Selective Dioxane-Mediated Aerobic Oxidation of Isoindolines
Thapa, Pawan,Corral, Esai,Sardar, Sinjinee,Pierce, Brad S.,Foss, Frank W.
, p. 1025 - 1034 (2019/01/24)
N-Alkyl and N-aryl-isoindolinones were prepared by a dioxane-mediated oxidation of isoindoline precursors. The transformation exhibits unique chemoselectivity for isoindonlines. A chiral tertiary (3°)-benzylic position was not racemized during oxidation, and methyl indoprofen was prepared by late stage oxidation. Mechanistic studies suggest a selective H atom transfer, which avoids many known oxidation (by-)products of isoindolinones.
Self-assembled aromatic molecules as efficient organic structure directing agents to synthesize the silicoaluminophosphate SAPO-42 with isolated Si species
Martínez-Franco, Raquel,Cantín, ángel,Vidal-Moya, Alejandro,Moliner, Manuel,Corma, Avelino
, p. 2981 - 2989 (2015/05/13)
The use of self-assembled aromatic molecules through π-π interactions has allowed the preparation of the silicoaluminophosphate (SAPO) form of the LTA, SAPO-42, with controlled Si content as isolated Si sites in the framework, and high thermal stability. Different SAPO-42 zeotypes can be synthesized with different acidity, morphology, and crystal size, depending on the selected quinolinium derived aromatic molecule as OSDA and the amount of fluoride content in the synthesis gels.
