Synthesis and physico-chemical properties of nitrocaffeic acids

Grenier, Jean-Luc; Cotelle, Nicole; Catteau, Jean‐Pierre; Cotelle, Philippe

doi:10.1002/1099-1395(200009)13:9<511::aid-poc283>3.0.co;2-8

Cited by 13 publications

(10 citation statements)

References 25 publications

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“…Further, hydrolysis of 2 afforded 4‐hydroxy‐3‐methoxy‐2‐nitro‐benzaldehyde ( 3 ) as a yellow crystal (sensitive to light). The melting points and the spectral data were consistent with the compounds 1 , 2 , 3 reported in literature .…”

Section: Resultssupporting

confidence: 89%

“…After removal of the solvent, the residue was washed with ice ethanol (3 × 10 mL) and dried to give 1 as white needles, 11.10 g (87%), mp 76–77°C (lit. [6a] mp 77°C, no range given); R f = 0.64 (petroleum ether–EtOAc, 2:1); IR (KBr): 2960, 2847, 1750 (C═O), 1680 (C═O), 1279, 1209 cm −1 ; 1 H‐NMR (CDCl 3 ): δ 2.35 (s, 3 H, COCH 3 ), 3.91 (s, 3 H, OCH 3 ), 7.23 (d, J = 7.6 Hz, 1 H, ArH), 7.52–7.46 (m, 2 H, ArH), 9.95 (s, 1 H, CHO); 13 C‐NMR (CDCl 3 ): δ 20.75 (COCH 3 ), 56.18 (OCH 3 ), 110.89, 123.51, 124.84, 135.31, 145.00, 152.04 (C‐aryl), 168.46 (COCH 3 ), 191.16 (CHO); MS (EI, m/z ): 194 [M] + . The spectral data are in agreement with literature values.…”

Section: Methodsmentioning

confidence: 99%

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First Total Synthesis of 9‐Hydroxy‐8H‐pyrano[3,2‐f]indol‐2‐one

Wang

Zhang

et al. 2014

Journal of Heterocyclic Chem

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A simple and efficient approach to synthesize a novel pyrrolocoumarin 9-hydroxy-8H-pyrano[3,2-f]indol-2-one (7) has been described. Starting from vanillin, the key intermediate 7-methoxy-1H-indol-6-yl propiolate (6) was synthesized in six steps. Then, the target compound was obtained by forming pyrone-ring and demethylation simultaneously in one step. A plausible mechanism invoking PtCl 4 catalyzed one-step reaction of cyclization and demethylation was also presented.

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Section: Resultssupporting

confidence: 89%

Section: Methodsmentioning

confidence: 99%

First Total Synthesis of 9‐Hydroxy‐8H‐pyrano[3,2‐f]indol‐2‐one

Wang

Zhang

et al. 2014

Journal of Heterocyclic Chem

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“…The reason we used chitosan as a shell material is its easy availability and environmental friendliness. For an improvement of its affinity to the framework, the chitosan was grafted with catecholic moieties that are apt to coordinate with the Fe 3 O 4 /C microtubes. , The presence of the nitro group effectively retards the oxidation of catecholic moieties because of its electron-withdrawing nature . It is noted that the Fe 3 O 4 /C framework changed from hydrophobicity to superhydrophilicity with a water contact near 0° after wrapping with CNC (Figure S7, Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

“…52,53 The presence of the nitro group effectively retards the oxidation of catecholic moieties because of its electron-withdrawing nature. 54 It is noted that the Fe 3 O 4 /C framework changed from hydrophobicity to superhydrophilicity with a water contact near 0°a fter wrapping with CNC (Figure S7, Supporting Information).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Mussel-Inspired Self-Healing of Ultralight Magnetic Frameworks

Chen

Pan

2017

ACS Sustainable Chem. Eng.

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Ultralight materials have many important applications, but most of them are unable to spontaneously recover their microstructure and functions after physical damage or abuse. Here we report an ultralight magnetic framework that can repair its broken microstructure autonomously via a mussel-inspired strategy. The self-healable framework consists of three-dimensionally (3D) interconnected Fe3O4/C microtubes wrapped with nanoshells of nitrocatechol-substituted chitosan. The framework spontaneously recovers its configuration integrity and mechanical properties during all 6 breaking/healing cycles through pH-induced coordination between Fe3+ and catecholic moieties. On the basis of the self-healable property, the framework can even be tailored into complicated patterns. The investigation offers a strategy to fabricate multifunctional ultralight materials with a self-healable property and tailorability, which have potential applications in adsorption, energy-storage, and catalysis, and so on.

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“…Compound (I) was synthesized according to the method reported by Grenier et al (2000). Single crystals were obtained by slow evaporation of a methanol/water solution (1:1).…”

Section: Methodsmentioning

confidence: 99%

3-(4-Hydroxy-3-methoxy-2-nitrophenyl)acrylic acid

Xia¹,

Hu²,

Zhou³

2006

Acta Cryst E

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Key indicatorsSingle-crystal X-ray study T = 298 K Mean (C-C) = 0.006 Å Disorder in main residue R factor = 0.095 wR factor = 0.243 Data-to-parameter ratio = 12.2 For details of how these key indicators were automatically derived from the article, seeThe title compound, C 10 H 9 NO 6 , has an E configuration, with the carboxyl group and the benzene ring located on opposite sides of the C C bond. Intermolecular O-HÁ Á ÁO hydrogen bonding helps to stabilize the crystal structure.

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Synthesis and physico-chemical properties of nitrocaffeic acids

Cited by 13 publications

References 25 publications

First Total Synthesis of 9‐Hydroxy‐8H‐pyrano[3,2‐f]indol‐2‐one

First Total Synthesis of 9‐Hydroxy‐8H‐pyrano[3,2‐f]indol‐2‐one

Mussel-Inspired Self-Healing of Ultralight Magnetic Frameworks

3-(4-Hydroxy-3-methoxy-2-nitrophenyl)acrylic acid

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