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Cas Database

80542-40-1

80542-40-1

Identification

  • Product Name:N-cinnamylidene-p-anisidine

  • CAS Number: 80542-40-1

  • EINECS:

  • Molecular Weight:237.301

  • Molecular Formula: C16H15NO

  • HS Code:

  • Mol File:80542-40-1.mol

Synonyms:N-cinnamylidene-p-anisidine

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Relevant articles and documentsAll total 49 Articles be found

Nickel Catalyzed Imine Aldol Reactions between Activated Imines and Pronucleophiles

Shida, Naomi,Kubota, Yasufumi,Fukui, Hiroyuki,Asao, Naoki,Kadota, Isao,Yamamoto, Yoshinori

, p. 5023 - 5026 (1995)

Treatment of activated imines 1 with carbonyl compounds 2 in the presence of catalytic amounts of NiCl2(PPh3)2 or NiBr2(PPh3)2 at room temperature affords imine aldol products 3 in high to good yields.

A new tool to guide halofunctionalization reactions: The halenium affinity (HalA) scale

Ashtekar, Kumar Dilip,Marzijarani, Nastaran Salehi,Jaganathan, Arvind,Holmes, Daniel,Jackson, James E.,Borhan, Babak

, p. 13355 - 13362 (2014)

We introduce a previously unexplored parameter - halenium affinity (HalA)- as a quantitative descriptor of the bond strengths of various functional groups to halenium ions. The HalA scale ranks potential halenium ion acceptors based on their ability to stabilize a "free halenium ion". Alkenes in particular but other Lewis bases as well, such as amines, amides, carbonyls, and ether oxygen atoms, etc., have been classified on the HalA scale. This indirect approach enables a rapid and straightforward prediction of chemoselectivity for systems involved in halofunctionalization reactions that have multiple nucleophilic sites. The influences of subtle electronic and steric variations, as well as the less predictable anchimeric and stereoelectronic effects, are intrinsically accounted for by HalA computations, providing quantitative assessments beyond simple "chemical intuition". This combined theoretical-experimental approach offers an expeditious means of predicting and identifying unprecedented reactions.

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

(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

4-methoxy-aniline
104-94-9

4-methoxy-aniline

N-cinnamylidene-p-anisidine
80542-40-1

N-cinnamylidene-p-anisidine

Conditions
Conditions Yield
With magnesium sulfate; In ethyl acetate; at 20 ℃; Inert atmosphere;
100%
Ambient temperature;
98%
In toluene; for 3.5h; Reflux;
90%
With magnesium sulfate; In dichloromethane; at 0 ℃; for 2h;
88%
In diethyl ether; at 20 ℃; for 2h;
83%
In methanol; at 60 ℃; for 0.5h; Microwave irradiation;
83%
With magnesium sulfate; In toluene; at 23 ℃; for 12h; Inert atmosphere;
65%
In dichloromethane; or in benzene;
With magnesium sulfate; In dichloromethane; for 15h; Ambient temperature;
In ethanol; for 1h; Heating;
In dichloromethane; at 20 ℃;
In tetrahydrofuran; for 0.5h; Heating;
With magnesium sulfate; In dichloromethane; at 20 ℃;
In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;
With magnesium sulfate; In dichloromethane;
for 0.166667h; Inert atmosphere;
100 %Spectr.
In dichloromethane; at 20 ℃; for 2h; Molecular sieve; Inert atmosphere;
With magnesium sulfate; In dichloromethane; at 20 ℃; for 24h;
In toluene; Reflux; Inert atmosphere;
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 ℃;
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%
4-methoxy-aniline
104-94-9

4-methoxy-aniline

3-phenyl-propenal
104-55-2

3-phenyl-propenal

N-cinnamylidene-p-anisidine
80542-40-1

N-cinnamylidene-p-anisidine

Conditions
Conditions Yield
In dichloromethane;
With magnesium sulfate; In acetonitrile; at 25 ℃; for 0.5h;
With magnesium sulfate; In tetrahydrofuran; at 20 ℃; Inert atmosphere;
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;
phenylacetaldehyde
122-78-1

phenylacetaldehyde

4-methoxy-aniline
104-94-9

4-methoxy-aniline

N-cinnamylidene-p-anisidine
80542-40-1

N-cinnamylidene-p-anisidine

Conditions
Conditions Yield
With molecular sieve; In toluene; for 24h; Ambient temperature;

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