1936-63-6

Usage

InChI:InChI=1/C9H13NO/c10-7-6-9(11)8-4-2-1-3-5-8/h1-5,9,11H,6-7,10H2

Upstream product

• 96-09-3 styrene oxide 
• 4937-87-5 N-hydroxy-2-oxo-2-phenylethanimidoyl chloride 
• 3282-32-4 2-diazo-acetophenone 
• 4410-31-5 (RS)-mandelamide 
• 35645-98-8 2-(2-hydroxy-2-phenyl-ethyl)-isoindole-1,3-dione 
• 613-89-8 2-Aminoacetophenone 
• 17918-11-5 1-(2'-hydroxy-2'-phenylethyl)aziridine 
• 119718-87-5 cyano(phenyl)methyl acetate 
• 51411-44-0 2-diphenylmethylenamino-1-phenylethanol 
• 64-04-0 phenethylamine 
• 75-52-5 nitromethane 
• 100-52-7 benzaldehyde 
• 70-11-1 α-bromoacetophenone 
• 100-42-5 styrene 

Downstream Products

• 79365-85-8 bis-(β-hydroxy-phenethyl)-amine 
• 110057-85-7 tris-(β-hydroxy-phenethyl)-amine 
• 82709-53-3 piperonal-(β-hydroxy-phenethylimine) 
• 34119-82-9 2-(benzoylamino)-1-phenylethanol 
• 867171-87-7 trichophysine 
• 7568-44-7 1,4-bis-(2-hydroxy-2-phenyl-ethyl)-piperazine-2,5-dione 
• 76133-73-8 dichloro-acetic acid-(β-hydroxy-phenethylamide) 
• 107154-09-6 N-(β-hydroxy-phenethyl)-benzamidine 
• 94209-62-8 4-[(2-hydroxy-2-phenyl-ethylamino)-methylene]-2-phenyl-4H-oxazol-5-one 
• 5493-95-8 6-phenylmorpholin-3-one 
• 18334-64-0 2,7-diphenyl-1,6-dioxa-4,9-diaza-5λ⁵-phospha-spiro[4.4]nonane 
• 59801-46-6 2-(1,1-dioxo-1λ⁶-thiomorpholin-4-yl)-1-phenyl-ethanol 
• 24703-90-0 5-methyl-5'-phenyl-2λ⁵-spiro[benzo[1,3,2]dioxaphosphole-2,2'-[1,3,2]oxazaphospholidine] 
• 3306-05-6 N-(2-hydroxy-2-phenylethyl)acetamide 

Relevant academic research and scientific papers

Montmorillonite-K10 catalyzed addition of trimethylsilylcyanide (TMSCN) to aldehydes

Addition of trimethylsilyl cyanide (TMSCN) to aldehydes was catalyzed by Montmorillonite-K10, with subsequent reduction to β-aminoalcohol.

β-amino alcohol properfumes

Amino-alcohol derivatives of fragrant, volatile aldehydes and ketones were synthesized in a one-pot procedure by sequential cyanohydrin formation with trimethylsilyl cyanide and reduction with lithium aluminium hydride, or by ammonolysis of epoxide precursors. The amino alcohols are nonvolatile, stable properfumes releasing fragrant carbonyls by oxidation with sodium periodate or sodium bismuthate. Examples include amino alcohol properfumes of citronellal, Lilial, lauryl aldehyde, menthone, benzaldehyde, and anisaldehyde.

Selective oxidation of thioanisole with hydrogen peroxide using copper complexes encapsulated in zeolite: Formation of a thermally stable and reactive copper hydroperoxo species

[Cu(terpy)]2+ complexes encapsulated into Na-Y zeolite ([Cu(terpy)]2+@Y) were prepared, and their catalytic activities for the oxidation of sulfides using hydrogen peroxide were investigated. Several spectroscopic results, as well as elemental analysis, demonstrated the formation of [Cu(terpy)]2+ complexes in supercages of Y-zeolite. [Cu(terpy)]2+@Y exhibited high selectivity for the oxidation of thioanisole into methylphenylsulfoxide when H2O2 was used. The kinetic study of this oxidation at the catalyst [Cu(terpy)]2+@Y suggests that the reaction of [Cu(terpy)]2+ species with H2O2 is the rate-determining step. The oxidation of thioanisole, benzene, and 2-phenylethylamine using [[Cu(terpy)]2+@Y]?, which was prepared from the reaction between [Cu(terpy)]2+@Y and H2O2, quantitatively proceeded to methylphenylsulfoxide, phenol, and 2-amino-1-phenylethanol, respectively. The reaction of [Cu(terpy)]2+@Y and H2O2 was found to yield thermally stable but active CuII-OOH species in [Cu(terpy)]2+@Y.

Heterogenization of chiral mono oxazoline ligands by grafting onto mesoporous silica MCM-41 and their application in copper-catalyzed asymmetric allylic oxidation of cyclic olefins

A series of chiral 4-oxazolinylaniline ligands 8 were conveniently synthesized on a gram scale from inexpensive and commercially available 4-aminobenzoic acid in four steps. The obtained organic chiral ligands have been covalently grafted onto ordered mesoporous silicas MCM-41 and the resulting inorganic–organic hybrid materials have been characterized by thermogravimetric analysis (TGA), differential thermal analysis (DTA), powder X-ray diffraction, BET and BJH nitrogen adsorption–desorption methods, energy-dispersive X-ray spectroscopy (EDX), CHN analysis, scanning electron microscopy (SEM), and Fourier transform infrared spectroscopy (FT-IR). The catalytic and induced asymmetric effects of the chiral copper (I) complexes of these new chiral supported heterogeneous catalysts on the asymmetric allylic oxidation of cycloolefins were investigated under different conditions. Reactions using the catalyst exhibited moderate to good enantioselectivities, up to 80%, and good yields, up to 95% better than the corresponding homogeneous reaction. The catalyst could be recovered easily and reused five times without remarkable loss of reactivity, yield, or enantioselectivity. This is, to the best of our knowledge, the first heterogenization of chiral 4-oxazolinylaniline ligands on an inorganic (silica) surface and their application as a heterogeneous catalyst in the asymmetric Kharash–Sosnovsky reaction.

Two efficient enantioselective syntheses of 2-amino-1-phenylethanol

Two enantioselective methods for the synthesis of 2-amino-1-phenylethanol have been developed. The first utilizes an enantioselective oxazaborolidine- catalyzed borane reduction of 2-chloroacetophenone (phenacyl chloride) to give the chiral chloro alcohol in good yield with an ee in the 93-97% range. Reaction with dilute ammonium hydroxide produced the amino alcohol in good yield with a high ee. The second approach involved first the conversion of phenacyl chloride to the succinimido acetophenone which was then hydrogenated using a chiral ruthenium complex in conjunction with a base and an optically active amine (Noyori procedure). This gave the optically active succinimido alcohol in very good yield with an ee of 98%. Hydrolysis with dilute base produced the optically active amino alcohol in very good yield and excellent enantioselectivity.

Overcoming thermodynamic and kinetic limitations of aldolase-catalyzed reactions by applying multienzymatic dynamic kinetic asymmetric transformations

(Figure Presented) Dynamic and successful: The asymmetric synthesis of 2-amino-1-phenylethanol was achieved by aminomethylation of benzaldehyde in the presence of the two enzymes L-threonine aldolase and L-tyrosine decarboxylase in a novel one-pot, two-enzyme process (see scheme). A modified method with three enzymes led to the enantioenriched amino alcohol in very high yield.

Highly enantioselective asymmetric transfer hydrogenation (ATH) of α-phthalimide ketones

A mild catalyst system for the synthesis of chiral amino alcohols via asymmetric transfer hydrogenation (ATH) of α-phthalimide ketones has been developed by using a chiral Ru-TsDPEN complex as the catalyst in DMF/MeOH at 40 °C. The reaction exhibits high reaction activity and excellent enantioselectivity where up to 96% yield and 99% ee of the product were obtained.

Application of an Electrochemical Microflow Reactor for Cyanosilylation: Machine Learning-Assisted Exploration of Suitable Reaction Conditions for Semi-Large-Scale Synthesis

Cyanosilylation of carbonyl compounds provides protected cyanohydrins, which can be converted into many kinds of compounds such as amino alcohols, amides, esters, and carboxylic acids. In particular, the use of trimethylsilyl cyanide as the sole carbon source can avoid the need for more toxic inorganic cyanides. In this paper, we describe an electrochemically initiated cyanosilylation of carbonyl compounds and its application to a microflow reactor. Furthermore, to identify suitable reaction conditions, which reflect considerations beyond simply a high yield, we demonstrate machine learning-assisted optimization. Machine learning can be used to adjust the current and flow rate at the same time and identify the conditions needed to achieve the best productivity.

Catalyst-Free Electrophilic Ring Expansion of N-Unprotected Aziridines with α-Oxoketenes to Efficient Access 2-Alkylidene-1,3-Oxazolidines

2-(2-Oxoalkylidene)-1,3-oxazolidine derivatives were synthesized in good to excellent yields regiospecifically through the catalyst-free electrophilic ring expansion of N-unprotected aziridines and the ketene C=O double bond of α-oxoketenes, in situ generated from the microwave-assisted Wolff rearrangement of 2-diazo-1,3-diketones. The ring expansion predominantly underwent an SN1 process and the hydrogen bond decides the (E)-configuration of products. (Figure presented.).

Method for synthesizing chiral alpha-amino alcohol compound

The invention discloses a method for synthesizing a chiral alpha-amino alcohol compound. The method comprises the following steps: sequentially adding an iron catalyst, a ligand, ketone, an organic solvent and silane into a reaction system at 20-30 DEG C in a nitrogen atmosphere, then stirring the obtained mixture, and carrying out column chromatography separation on the obtained product to obtain a product, namely chiral alpha-amino alcohol. According to the invention, the most high-yield iron catalyst in earth crust is used, and cheap silane (PMHS, 500 g/298 yuan) is adopted as a reducing agent, so the asymmetric reduction reaction of alpha-amino ketone can be efficiently achieved under mild conditions so as to obtain the high-yield optically-active chiral alpha-amino alcohol compound; and moreover, through the creative labor of the inventor, reaction yield can reach 99%, and meanwhile, the content of the target product in the generated reaction product is 99%.