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Cas Database

88315-63-3

88315-63-3

Identification

  • Product Name:(E)-4-methoxy-N-((E)-3-phenylallylidene)aniline

  • CAS Number: 88315-63-3

  • EINECS:

  • Molecular Weight:237.301

  • Molecular Formula: C16H15NO

  • HS Code:

  • Mol File:88315-63-3.mol

Synonyms:(E)-4-methoxy-N-((E)-3-phenylallylidene)aniline

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Relevant articles and documentsAll total 39 Articles be found

A Novel ZnII Complex Bearing Two Monodentate (4-Methoxyphenyl)[(1E, 2E)-3-phenylprop-2-en-1-ilidene] Schiff Bases: Crystal Structure and DFT Study

Cordeiro, Giuliano M.,Hottes, Emanoel,Esteves-Souza, Andressa,Guedes, Guilherme P.,De Sant'Anna, Carlos Maurício R.,Herbst, Marcelo H.

, (2019)

A novel ZnII complex bearing two monodentate (4-methoxyphenyl)[(1E, 2E)-3-phenylprop-2-en-1-ilidene] Schiff bases was synthesized and investigated both in the solid state by single-crystal X-ray diffraction, elemental analysis, and FTIR and in

Synthesis of β-Phosphinolactams from Phosphenes and Imines

Fu, Xingyang,Li, Xinyao,Xu, Jiaxi

supporting information, p. 8733 - 8737 (2021/11/17)

Various cis-β-phosphinolactams are synthesized stereoselectively for the first time from imines and diazo(aryl)methyl(diaryl)phosphine oxides under microwave irradiation. Diazo(aryl)methyl(diaryl)phosphine oxides first undergo the Wolf rearrangement to generate phosphenes. Imines nucleophilically attack the phosphenes followed by an intramolecular nucleophilic addition via less steric transition states to give final cis-β-phosphinolactams. C-Styrylimines generally give rise to β-phosphinolactams in higher yields than C-arylimines. The stereoselectivity and proposed mechanism are rationalized by DFT theoretical calculation.

Iron-Catalyzed Hydrogen Transfer Reduction of Nitroarenes with Alcohols: Synthesis of Imines and Aza Heterocycles

Wu, Jiajun,Darcel, Christophe

, p. 1023 - 1036 (2021/01/09)

A straightforward and selective reduction of nitroarenes with various alcohols was efficiently developed using an iron catalyst via a hydrogen transfer methodology. This protocol led specifically to imines in 30-91% yields, with a good functional group tolerance. Noticeably, starting from o-nitroaniline derivatives, in the presence of alcohols, benzimidazoles can be obtained in 64-72% yields when the reaction was performed with an additional oxidant, DDQ, and quinoxalines were prepared from 1,2-diols in 28-96% yields. This methodology, unprecedented at iron for imines, also provides a sustainable alternative for the preparation of quinoxalines and benzimidazoles.

Synthesis, characterization, molecular structure and computational study of tetrahedral pentamethylcyclopentadienyl iridacycle complexes with α,β-conjugated Schiff base ligands

Daud, Adibah Izzati,Khairul, Wan M.,Liu, Zhi-Qiang,Ong, Kok Tong,Tay, Meng Guan

, (2020/09/16)

Due to the excellent catalytic activities and phosphorescent properties that iridium complexes display, iridium chemistry has been of great interest for scientific investigation over the past 30 years. Iridium metallacycle analogues (also known as an iridacycles) bearing phenylpyridine (ppy) ligands have been well reported on, whilst complexes with R-phenyl-(3-R-phenylallylidene)amine, which is an α,β-conjugated Schiff base ligand, have not had the same attention, despite the fact that both ligands share a similar coordination mode. In this research, four pentamethylcyclopentadienyl iridacycle complexes, Ir1a-Ir1d, with different α,β-conjugated Schiff base ligands were synthesized from a di-μ-chloro-dichloro-bis-(η5-pentamethylcyclopentadienyl)diiridium(III) precursor. The iridacycle complexes were characterized using spectroscopic techniques and the molecular structures of Ir1ab-Ir1d were determined using X-ray crystallography. The X-ray results revealed that the iridacycle complexes have a tetrahedral geometry, the iridium centre being coordinated through the N[dbnd]C[sbnd]Cα[dbnd]Cβ moiety of the α,β-conjugated Schiff base ligand. Computational calculations with the B3LYP method and with LanL2DZ basis sets indicated that the HOMO-LUMO energy gaps Ir1b-Ir1d were in the range 3.31–3.36 eV. The OMe substituent at the C terminal has a greater impact on the HOMO energy level than the one at the N terminal.

Stereoselective Construction of γ-Lactams via Copper-Catalyzed Borylacylation

Bajohr, Jonathan,Lautens, Mark,Polishchuk, Iuliia,Torelli, Alexa,Whyte, Andrew

supporting information, p. 7915 - 7919 (2020/11/02)

A versatile and highly stereoselective borylative cyclization to generate polyfunctionalized γ-lactams has been developed. The stereoselective synthesis of these key ring systems is crucial due to their ubiquity in natural products. We report the diastero- and enantioselective construction of di- and trisubstituted γ-lactam cores, with examples containing an enantioenriched quaternary carbon.

Promoting Frustrated Lewis Pairs for Heterogeneous Chemoselective Hydrogenation via the Tailored Pore Environment within Metal–Organic Frameworks

Niu, Zheng,Zhang, Weijie,Lan, Pui Ching,Aguila, Briana,Ma, Shengqian

supporting information, p. 7420 - 7424 (2019/04/27)

Frustrated Lewis pairs (FLPs) have recently been advanced as efficient metal-free catalysts for catalytic hydrogenation, but their performance in chemoselective hydrogenation, particularly in heterogeneous systems, has not yet been achieved. Herein, we demonstrate that, via tailoring the pore environment within metal–organic frameworks (MOFs), FLPs not only can be stabilized but also can develop interesting performance in the chemoselective hydrogenation of α,β-unsaturated organic compounds, which cannot be achieved with FLPs in a homogeneous system. Using hydrogen gas under moderate pressure, the FLP anchored within a MOF that features open metal sites and hydroxy groups on the pore walls can serve as a highly efficient heterogeneous catalyst to selectively reduce the imine bond in α,β-unsaturated imine substrates to afford unsaturated amine compounds.

Process route upstream and downstream products

Process route

4-methoxy-aniline
104-94-9

4-methoxy-aniline

3-phenyl-propenal
104-55-2

3-phenyl-propenal

(E)-4-methoxy-N-((E)-3-phenylallylidene)aniline
88315-63-3

(E)-4-methoxy-N-((E)-3-phenylallylidene)aniline

Conditions
Conditions Yield
With silica gel; In neat (no solvent); for 1h; Milling;
95%
In ethanol; at 20 ℃; for 1h;
78%
With toluene-4-sulfonic acid; In benzene; for 6h; Heating;
61%
With magnesium sulfate; In dichloromethane; for 10h; Ambient temperature;
4-methoxy-aniline
104-94-9

4-methoxy-aniline

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
Conditions Yield
piperidine; In ethanol; for 5h; Heating;
100%
With magnesium sulfate; In dichloromethane; at 20 ℃;
100%
In ethyl 2-hydroxypropionate; water; at 20 ℃; for 0.025h;
96%
In ethanol;
90%
With magnesium sulfate; In dichloromethane; at 20 ℃; for 6h; Schlenk technique; Inert atmosphere;
80%
In ethanol; Heating;
62%
In dichloromethane; Inert atmosphere; Molecular sieve;
59%
With ethanol;
In ethanol; for 1h; Heating;
In ethanol; Reflux;
With MgI2 etherate [(MgI2.OEt2)n]; In dichloromethane; at 20 ℃; for 0.166667h;
With sodium sulfate; In dichloromethane; at 20 ℃; for 24h;
With magnesium sulfate; at 20 ℃; Inert atmosphere;
In toluene; at 100 ℃; for 1h; Molecular sieve; Inert atmosphere;
In methanol; at 60 ℃; for 3h;
With magnesium sulfate; In dichloromethane; at 20 ℃;
With Amberlyst; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere;
With magnesium sulfate; In dichloromethane; at 20 ℃;
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

4-methoxy-aniline
104-94-9

4-methoxy-aniline

(E)-4-methoxy-N-((E)-3-phenylallylidene)aniline
88315-63-3

(E)-4-methoxy-N-((E)-3-phenylallylidene)aniline

Conditions
Conditions Yield
With magnesium sulfate; In dichloromethane; for 4h; Ambient temperature;
100%
With magnesium sulfate; In ethyl acetate; for 1h; Ambient temperature;
100%
In neat (no solvent); for 0.25h;
100%
In ethanol; at 20 ℃; Inert atmosphere;
98%
95%
With sodium sulfate; In diethyl ether; at 20 ℃; Inert atmosphere; Schlenk technique;
59%
In chloroform; for 6h; Ambient temperature; molecular sieves;
With magnesium sulfate; In dichloromethane; Ambient temperature;
p-methoxy-phenylazide
2101-87-3

p-methoxy-phenylazide

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
Conditions Yield
With poly(styrene-co-3-maleimidophenyldiphenylphosphine); In tetrahydrofuran; at 20 ℃; for 43h;
97%
N-cinnamyl-4-methoxybenzenamine
22774-93-2

N-cinnamyl-4-methoxybenzenamine

Conditions
Conditions Yield
With tert.-butylhydroperoxide; tris(triphenylphosphine)ruthenium(II) chloride; In benzene; Ambient temperature;
80%
para-methoxynitrobenzene
100-17-4

para-methoxynitrobenzene

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
Conditions Yield
With potassium phosphate monohydrate; trimethylamine-N-oxide; C18H27FeO4Si2; In toluene; at 140 ℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube;
58%
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

4-methoxy-aniline
104-94-9

4-methoxy-aniline

Conditions
Conditions Yield
With magnesium sulfate; In benzene; at 20 ℃;
benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: toluene / 17 h / 85 °C
2: magnesium sulfate / dichloromethane / 20 °C
With magnesium sulfate; In dichloromethane; toluene; 1: |Wittig Olefination;
phenylboronic acid
98-80-6

phenylboronic acid

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: palladium diacetate; 2.9-dimethyl-1,10-phenanthroline; p-benzoquinone / N,N-dimethyl-formamide / 48.5 h / 20 °C
2: magnesium sulfate / dichloromethane / 20 °C
With 2.9-dimethyl-1,10-phenanthroline; palladium diacetate; magnesium sulfate; p-benzoquinone; In dichloromethane; N,N-dimethyl-formamide; 1: |Heck Reaction;
Conditions
Conditions Yield
96%
entspr. Aldehyd, entspr. Amin;
Benzaldehyd, Phosphoniumsalz 9b;
Zimtaldehyd, p-Anisidin;
entspr. Allylamin, MnO2;
p-Anisidin, N-Cinnamyliden-4-nitro-anilin, beide in abs. Me., Siedetemp., 30 Std.;

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