31886-57-4

Usage

Uses

Used in Chemical Synthesis:
(S)-(-)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE is used as a starting material for the synthesis of chiral diferrocenylphosphine-diamines, which are applicable in catalysis. The presence of the ferrocene group and the chiral center in (S)-(-)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE makes it a valuable precursor for the development of novel catalysts with potential applications in various chemical reactions.
Used in Analytical Chemistry:
(S)-(-)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE is used as a model chiral probe in the study of enantiodiscrimination ability of chiral ionic liquids using cyclic voltammetry. This application takes advantage of the compound's unique electronic properties and its ability to interact with chiral ionic liquids, providing insights into the development of new methods for enantiomeric separation and analysis.

InChI:InChI=1/C9H13N.C5H4.Fe/c1-8(10(2)3)9-6-4-5-7-9;1-2-4-5-3-1;/h4-6,8H,1-3H3;1-4H;/q2*-1;+2/t8-;;/m0../s1/rC14H17FeN/c1-11(16(2)3)13-9-6-10-14(13)15-12-7-4-5-8-12/h4-11H,1-3H3/t11-/m0/s1

Upstream product

• 124-40-3 dimethyl amine 
• 16940-66-2 sodium tetrahydroborate 
• 1085568-96-2 1-ferrocenylethylamine 
• 1277-49-2 1-ferrocenylethanol 
• 50-00-0 formaldehyd 
• 1271-55-2 acetylferrocene 
• 506-59-2 N,N-dimethylammonium chloride 
• 102-54-5 ferrocene 
• 75-07-0 acetaldehyde 
• 123-63-7 paracetaldehyde 
• 51-80-9 bis-(dimethylamino)methane 

Downstream Products

• 1271-51-8 vinyl ferrocene 
• 1271-55-2 acetylferrocene 
• 263026-96-6 N,N-dimethyl-(1',2-bis(diphenylphosphino)ferrocenyl)-1-(methyl-1-methylamine) 

Relevant academic research and scientific papers

Circular dichroism of R- and S-enantiomers of Ugi′s amine and their conjugates with l-tartaric acid

Circular dichroism spectra of the optically active (R)- and (S)-enantiomers of N,N-(dimethylamino)ethylferrocene (Ugi′s amine) were studied for a free form and for their diastereomeric salts with с l(+)-tartaric acid.

One-pot α-ferrocenylalkylation of amines and alcohols with α-ferrocenyl substituted alcohols under acid-free conditions

One-pot reaction of FcCH(R)OH with equimolar quantities of BunLi and EtOCOCl followed by an excess of amine produces N-(α-ferrocenylalkyl)amines in up to 98% yields. Nitrogen heteroaryl amines undergo the α-ferrocenylalkylation at the amino group. The α-ferrocenylalkylation of alcohols and phenols (R'OH) leads to a formation of ethers FcCH(R)OR′ in lower yields. The reactions proceed via an intermediate formation of α-ferrocenylalkyl carbonates FcCH(R)OCOOEt. The side reactions associated with this protocol are discussed.

Synthetic method of Ugi's amines and derivatives of Ugi's amines

The invention discloses a synthetic method of Ugi's amines and derivatives of the Ugi's amines represented by a formula (I) shown in the description. The method comprises the following steps: performing reductive amination by using ferrocene and a derivative of the ferrocene as raw materials to obtain a racemic primary amine, performing resolution on the racemic primary amine by a resolving agentto obtain an optical isomer primary amine, performing an alkylation or reductive amination reaction on the optical isomer primary amine to obtain one Ugi's amine and the derivative of the Ugi's amine.The chiral Ugi's amines and the derivatives of the Ugi's amines provided by the invention can be used to synthesize a series of Josiphos-like ferrocene bisphosphine ligands, the Josiphos-like ferrocene bisphosphine ligands are used as chiral ligands for various metal complex catalysts, are important chiral catalyst ligands for preparation of pharmaceutical intermediates and agrochemicals, have awide range of applications in metal catalysis asymmetric reactions, and are suitable for industrialized large-scale production; and the reaction conditions are mild, the raw materials are cheap and easy to obtain, the synthetic route is simple, and the yield and chiral purity are higher.

Process for preparing (S)-1-ferrocene ethyl dimethylamine

The invention discloses a process for preparing (S)-1-ferrocene ethyl dimethylamine. In the preparation process, acetylferrocene is used as a raw material, and a complex obtained by reacting a metal Ir complex with a chiral ferrocene tridentate ligand L* is used as a catalyst, (S)-1-ferrocenyl ethanol is prepared by asymmetric catalytic hydrogenation, and the(S)-1-ferrocene ethyl dimethylamine isprepared by acetylation and dimethylamine substitution reaction. Compared with a traditional chiral separation method for preparing the (S)-1-ferrocene ethyl dimethylamine, the process has main beneficial effects of mild reaction conditions, simple operation, good stereoselectivity, high yield, short production cycle, small amount of three wastes , easy industrialization, and large implementationvalue and social and economic benefits.

Rhodium-Catalyzed Asymmetric Allylation of Malononitriles as Masked Acyl Cyanide with Allenes: Efficient Access to β,γ-Unsaturated Carbonyls

A rhodium-catalyzed regio- and enantioselective intermolecular allylation of malononitriles as masked acyl cyanides (MAC) with terminal and symmetrical internal allenes is reported. A RhI/Josiphos catalytic system combined with subsequent oxidative degradation of the primary adducts enables a straightforward access to α-branched, β,γ-unsaturated carbonyl compounds. The present protocol exhibits perfect atom economy in the allylation step and is characterized by a great functional group compatibility. Furthermore, the use of α-substituted malononitriles allowed for the construction of all-carbon quaternary centers.

FUNCTIONALIZED MAGNETIC NANOPARTICLE, A CATALYST, A METHOD FOR FORMING C-C BONDS

A functionalized magnetic nanoparticle including an organometallic sandwich compound and a magnetic metal oxide. The functionalized magnetic nanoparticle may be reacted with a metal precursor to form a catalyst for various C—C bond forming reactions. The catalyst may be recovered with ease by attracting the catalyst with a magnet.

Insight into the Thermal Ring-Opening Polymerization of Phospha[1]ferrocenophanes

A mixture of cis/trans isomers of phospha[1]ferrocenophanes equipped with one iPr group at the α position to the bridging PhP moiety was prepared. Both isomers (cis-4 and trans-4) were obtained as racemates and could be separated so that their thermal properties were investigated individually. The molecular structure of cis-4 was determined by single-crystal X-ray analysis showing a tilt angle α=26.35(8)°. Interconversion between both isomers occurred in the melt at elevated temperatures and revealed that the trans isomer is thermodynamically more stable. Structural and thermodynamic data was complemented by DFT calculations (B3PW91/6-311+G(d,p) and B3PW91-D3(BJ)/6-311+G(d,p)). Performance of thermal ring-opening polymerization (ROP) of trans-4 at 230 °C gave polymers and cyclic oligomers. Gel permeation chromatography (GPC) of the sulfurized polymer resulted in a molecular weight of 62.5 kDa (Mw) and a polydispersity index of 1.39 (PDI). Mass spectrometric analysis of the oligomers showed the presence of cyclic species from dimers to heptamers. After sulfurization, preparative thin layer chromatography led to the separation of three isomeric dimers. Structural characterization of these dimers by single-crystal X-ray analysis led to the conclusion that the Fe?Cp bond breaks during the thermal ROP process. A mechanism similar to the known mechanism of the photolytic ROP of ferrocenophanes is proposed.

Enantiopure Ferrocene-Based Planar-Chiral Iridacycles: Stereospecific Control of Iridium-Centred Chirality

Reaction of [IrCp?Cl2]2 with ferrocenylimines (Fc=NAr, Ar=Ph, p-MeOC6H4) results in ferrocene C-H activation and the diastereoselective synthesis of half-sandwich iridacycles of relative configuration Sp?,RIr?. Extension to (S)-2-ferrocenyl-4-(1-methylethyl)oxazoline gave highly diastereoselective control over the new elements of planar chirality and metal-based pseudo-tetrahedral chirality, to give both neutral and cationic half-sandwich iridacycles of absolute configuration Sc,Sp,RIr. Substitution reactions proceed with retention of configuration, with the planar chirality controlling the metal-centred chirality through an iron-iridium interaction in the coordinatively unsaturated cationic intermediate.

Palladium-catalyzed reaction of 2-iodoferrocenyl alcohols with internal alkynes: Synthesis of functionally 1,2-disubstituted ferrocenes and ferroceno-pyrans

The reaction of racemic (2-iodoferrocenyl)methanol with internal alkynes in the presence of (dppf)PdCl2 and i-Pr2NH produces alkenyl-substituted ferrocene carboxaldehydes in moderate yields. All reactions are carried out at 100 or 120 °C for different reaction times (between 6 and 26 h) in a screw-cap Pyrex bottle. The scope and limitations of this reaction are studied by employing variously substituted 11 internal alkynes. The reactions are regioselective with alkynes having a sterically crowded substituent such as t-butyl and trimethylsilyl groups. Moreover, racemic 1-(2-iodoferrocenyl)ethanol derivatives are synthesized as two diastereomers. Both diastereomers are reacted with internal alkynes in the presence of (dppf)PdCl2 and i-Pr2NH at 120 °C to afford alkenyl-substituted acetylferrocenes and ferroceno-pyrans in moderate to good yields. According to the alkyne employed, different reaction times (between 6 and 55 h) are necessary to drive the reactions to completion. Mechanisms are also suggested for the formation of observed products.

Electrochemical Detection of Saccharides by the Redox Cycle of a Chiral Ferrocenylboronic Acid Derivative: a Novel Method for Sugar Sensing

A chiral ferrocenylboronic acid 1 bearing an intramolecular tertiary amine binds saccharides at ca. pH 7, the complexation event, which can be conveniently detected by an electrochemical method, shows chiral discrimination for certain linear saccharides.