91-03-2

Usage

Uses

Intermediate in the preparation of analgesics.

InChI:InChI=1/C12H17NO/c1-10(9-13(2)3)12(14)11-7-5-4-6-8-11/h4-8,10H,9H2,1-3H3/t10-/m1/s1

Upstream product

• 37471-46-8 1-phenyl-1-trimethylsiloxypropene 
• 25468-31-9 N-methyl-N-methylenemethanaminium 2,2,2-trifluoroacetate 
• 50-00-0 formaldehyd 
• 124-40-3 dimethyl amine 
• 93-55-0 1-phenyl-propan-1-one 
• 148932-08-5 α-Pyrrolidino-β-methyl styrene 
• 33797-51-2 eschenmoser's salt 
• 30354-18-8 N,N-dimethyl(methylene)ammonium chloride 
• 30931-91-0 N,N-dimethylmethyleneammonium tetrachloroaluminate 
• 7473-99-6 α-chloroisobutyrophenone 
• 611-70-1 phenyl isopropyl ketone 
• 138060-82-9 1-Phenyl-1-<(S)-2-(methoxymethyl)-1-pyrrolidyl>-1-propen 
• 51-80-9 bis-(dimethylamino)methane 
• 78024-09-6 cis-(n-Bu)2BOC(C₆H₅)CHCH₃ 

Downstream Products

• 854178-69-1 4-dimethylamino-3-methyl-2-phenyl-butan-2-ol 
• 2260-37-9 3-dimethylamino-2-methyl-1,1-diphenyl-propan-1-ol 
• 26171-50-6 (S)-3-dimethylamino-2-methyl-1-phenyl-propan-1-one 
• 126-04-5 (2RS,3SR)-4-dimethylamino-3-methyl-1,2-diphenyl-butan-2-ol 
• 126-04-5 (2RS,3RS)-4-dimethylamino-3-methyl-1,2-diphenyl-butan-2-ol 
• 910619-58-8 5-(Dimethylamino)-3-hydroxy-2,2,4-trimethyl-3-phenylpentannitril 
• 285124-04-1 3-[(4-methoxyphenyl)amino]-2-methyl-1-phenylpropan-1-one 
• 1019283-32-9 C₁₆H₂₁N₃S 
• 1019283-59-0 C₁₈H₁₉N₃S 
• 1019283-20-5 C₁₅H₂₁N₃S 
• 1019283-38-5 C₁₇H₂₃N₃S 
• 888955-68-8 1-thiocarbamoyl-3-phenyl-4-methyl-4,5-dihydropyrazole 
• 1019283-65-8 C₁₈H₁₈ClN₃S 
• 1019283-26-1 C₁₅H₂₁N₃S 

Relevant academic research and scientific papers

Stereoselective Synthesis of Functionalized Pyrrolidines by the Diverted N-H Insertion Reaction of Metallocarbenes with β-Aminoketone Derivatives

A highly stereoselective route to functionalized pyrrolidines by the metal-catalyzed diverted N-H insertion of a range of diazocarbonyl compounds with β-aminoketone derivatives is described. A number of catalysts (rhodium(II) carboxylate dimers, copper(I) triflate, and an iron(III) porphyrin) are shown to promote the process under mild conditions to give a wide range of highly substituted proline derivatives. The reaction starts as a metallocarbene N-H insertion but is diverted by an intermolecular aldol reaction. The metal-catalyzed reaction of diazocarbonyl compounds with β-aminoketone derivatives leads to highly substituted pyrrolidines with excellent diastereoselectivity under mild reaction conditions. The reaction starts as a metallocarbene N-H insertion but is diverted by an intermolecular aldol reaction.

Novel Pd(II) complexes of 1-N-substituted 3-phenyl-2-pyrazoline derivatives and evaluation of antiamoebic activity

Cyclization of Mannich base with N4-substituted thiosemicarbazides by different aliphatic, aromatic and cyclic amines afforded a series of new 1-N-substituted cyclised pyrazoline analogues of thiosemicarbazones (PYZ-TSC) 1-10. Reaction of [Pd(DMSO)2Cl2] with pyrazoline derivatives led to new palladium(II) complexes [Pd(PYZ-TSC)Cl2] 1a-10a. The structures of all the compounds were characterized by spectroscopic methods. It was concluded that the pyrazoline thiosemicarbazone derivatives have two chelating arms, one attached at the 2-position of the pyrazole ring (that is, N donor) and other (S donor) linked to the thiosemicarbazone branch. The determination of antiamoebic activity of all the compounds was done using HM1:IMSS strain of Entamoeba histolytica, among all the complexes, 8a showed the most promising IC50 = 0.37 μM vs. IC50 = 1.81 μM of metronidazole, the reference drug. MTT assay showed that the compounds are non-toxic to human kidney epithelial cell line.

Synthesis and pharmacological studies of 3-amino-2-methyl-1-phenylpropanones as hypolipidemic agents in rodents

A series of 3-amino-2-methyl-1-phenylpropanones were synthesized and proven to have potent hypolipidemic activity in rodents by lowering both serum cholesterol and triglyceride levels at 8 mg/kg/day, i.p. and orally. Many of these analogs showed significantly higher activity than standard drugs, lovastatin and clofibrate at their therapeutic doses. 2-Methyl-3-(perhydroazepin-1-yl)-1-phenylpropanone (4), 3-(4-methylpiperazin-1-yl)-1-phenylpropanone (5), and 2-methyl-3-(4-pyrrolidinocarbonylmethylpiperazin-1-yl)-1-(4-fluorophen yl)propanone (17) showed the best overall activities in lowering both serum cholesterol and triglyceride levels in CF1 mice at 8 mg/kg/day after 16 days of treatment. Compounds 4, 5,and 17 lowered serum cholesterol levels 63%, 58%, and 42%, respectively, after 16 days at 8 mg/kg/day i.p.. These agents reduced the serum triglyceride levels by 33%, 37%, and 54%, respectively. In Sprague-Dawley rats these compounds also demonstrated significant serum lipid lowering effects by decreasing both serum cholesterol and triglyceride levels after 14 days of oral drug administration at 8 mg/kg/day. Compound 17 reduced the rat aorta cholesterol levels by 37%, triglyceride levels by 50%, and neutral lipid levels by 34% after 14 days of oral administration. These compounds lowered the chylomicron, VLDL, and LDL cholesterol and triglyceride levels while elevating the HDL cholesterol levels significantly. In hyperlipidemic rodents, these analogs also demonstrated significant serum lipid lowering effects but were less active than in normolipidemic rodents. The activities of some enzymes, such as mouse hepatic acetyl CoA synthetase, HMG CoA reductase, phosphatidylate phosphohydrolase, and hepatic lipoprotein lipase, were significantly reduced by these compounds.

Stereocontrolled Syntheses of Mannich Bases and γ-Amino Alcohols

The reaction of enantiomerically pure SMP enamines 2 with iminium tetrachloroaluminates 3 yields optically active Mannich bases 4.Diastereoselective reduction of 4 gives γ-amino alcohols 5 with the desired configuration. Key Words: Mannich bases / Enamines / Iminium salts / γ-Amino alcohols

Mannich Reaction of Carbonyl Compounds via Boron Enolates and N,N,N',N'-Tetramethyldiaminomethane

A variety of carbonyl compounds undergo N,N-dimethylaminomethylation in moderate to good yields by the Mannich reaction involving boron enolates and N,N,N',N'-tetramethyldiaminomethane in dichloromethane.

α-Aminoalkylation of Enamines with Iminiumtetrachloro-aluminates

We report the use of iminiumtetrachloro-aluminates 1a, 2a, and 3a in Mannich reactions.These salts are easily synthesized and offer some important advantages compared to iminium salts 1b-e. - Keywords: Iminiumtetrachloro-aluminates, Preformed Mannich Salts, α-Aminoalkylation, Enamines

MANNICH REACTION UNDER HIGH PRESSURE. DIMETHYLAMINOMETHYLATION OF KETONES WITH BIS(DIMETHYLAMINO)METHANE UNDER MILD CONDITIONS

Dimethylaminomethylation of ketones with bis(dimethylamino)methane takes place cleanly in methanol at room temperature in the kiro bar region.

Carbon-Carbon Bond Formation by the Use of Chloroiodomethane as a C1 Unit. III. A Convenient Synthesis of the Mannich Base from Enol Silyl Ether by a Combination of Chloroiodomethane and N,N,N',N'-Tetramethylmethanediamine

The Mannich dimethylaminomethylation of carbonyl compounds is conveniently carried out via enol trimethylsilyl ethers by a combination of chloroiodomethane (CH2ClI) and N,N,N',N'-tetramethylmethanediamine (TMMD) in DMSO as the solvent at ambient temperatute.The mechanism of the transformation is discussed on the basis of product analysis and 1H NMR spectral studies.The reagent system CH2ClI/TMMD also provides a convenient route to the Eschenmoser's salt ().

THE MANNICH REACTION OF CARBONYL COMPOUNDS VIA SILYL ENOL ETHERS BY A COMBINATION OF CHLOROIODOMETHANE AND N,N,N',N'-TETRAMETHYLDIAMINOMETHANE

The Mannich dimethylaminomethylation of carbonyl compounds is conveniently carried out via trimethylsilyl enol ethers by a combination of chloroiodomethane and N,N,N',N'-tetramethyldiaminomethane in DMSO or DMF as the solvent at ambient temperature.