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Usage

Uses

Used in Organic Synthesis:
N-methyl-1,2-diphenylethanolamine is utilized as a reactant in organic synthesis, particularly for the production of pharmaceuticals and other fine chemicals. Its unique structure allows it to participate in various chemical reactions, contributing to the synthesis of complex organic molecules.
Used in Pharmaceutical Production:
In the pharmaceutical industry, N-methyl-1,2-diphenylethanolamine serves as a key intermediate in the synthesis of certain drugs. Its presence in the molecular structure of these drugs can influence their pharmacological properties and therapeutic effects.
Used as a Chiral Auxiliary in Asymmetric Catalysis Reactions:
N-methyl-1,2-diphenylethanolamine has been studied for its potential use as a chiral auxiliary in asymmetric catalysis. Its ability to induce chirality in reactions can lead to the production of enantiomerically pure compounds, which is crucial for the development of effective and selective drugs.
Used in the Development of New Drugs and Materials:
Due to its antioxidant properties, N-methyl-1,2-diphenylethanolamine has potential applications in the development of new drugs and materials. Its capacity to neutralize reactive oxygen species may contribute to the creation of compounds with therapeutic benefits or improved material properties.
Further research is necessary to fully explore the potential uses and properties of N-methyl-1,2-diphenylethanolamine, ensuring that its applications are maximized and its benefits realized across various industries.

InChI:InChI=1/C15H17NO/c1-16-14(12-8-4-2-5-9-12)15(17)13-10-6-3-7-11-13/h2-11,14-17H,1H3

Upstream product

• 301191-47-9 N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]formamide 
• 23190-16-1 (1R,2S)-2-Amino-1,2-diphenylethanol 
• 39664-88-5 N-[(1S,2R)-2-hydroxy-1,2-diphenylethyl]formamide 
• 611-71-2 (R)-Mandelic Acid 
• 17199-29-0 (S)-Mandelic acid 
• 134-81-6 benzil 
• 74-89-5 methylamine 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 64-17-5 ethanol 
• 530-36-9 erythro-2-amino-1,2-diphenylethanol 
• 74-88-4 methyl iodide 
• 39664-86-3 (+/-)-N-(erythro-α'-hydroxy-bibenzyl-α-yl)-formamide 
• 94675-08-8 (+/-)-N-(erythro-α'-hydroxy-bibenzyl-α-yl)-N-methyl-acetamide 
• 94675-08-8 (+/-)-N-(threo-α'-hydroxy-bibenzyl-α-yl)-N-methyl-acetamide 

Downstream Products

• 38057-82-8 3'-methyl-4',5'-diphenyl-2λ⁵-spiro[benzo[1,3,2]dioxaphosphole-2,2'-[1,3,2]oxazaphospholidine] 
• 38057-85-1 2,2,3,3,9-pentamethyl-7,8-diphenyl-1,4,6-trioxa-9-aza-5λ⁵-phospha-spiro[4.4]nonane 
• 38057-78-2 4,9-dimethyl-2,3,7,8-tetraphenyl-1,6-dioxa-4,9-diaza-5λ⁵-phospha-spiro[4.4]nonane 
• 550-58-3 N-methylamino-2 diphenyl-1,2 ethanol erythro 
• 550-58-3 DL-threo-2-methylamino-1.2-diphenyl-ethanol 
• 32461-34-0 3-methyl-4,5-diphenyl-oxazolidin-2-one 
• 32461-34-0 3-methyl-4,5-diphenyl-oxazolidin-2-one 
• 1081548-91-5 (1R,2R)-2-(methylamino)-1,2-diphenylethan-1-ol 
• 550-58-3 (1R,2S)-1,2-diphenyl-2-(N-methyl)aminoethanol 
• 1279115-37-5 C₁₅H₁₆N₂O₂ 
• 1279115-31-9 (1S,2S)-2-(1-methylhydrazino)-1,2-diphenylethanol fumarate 
• 1279115-30-8 (1S,2S)-2-(1-methylhydrazino)-1,2-diphenylethanol 
• 1380325-25-6 N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N-methylbutyramide 
• 1380325-29-0 N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N-methyl-2-methylenebutanamide 

Relevant academic research and scientific papers

Stereoinversion of Unactivated Alcohols by Tethered Sulfonamides

The direct, catalytic substitution of unactivated alcohols remains an undeveloped area of organic synthesis. Moreover, catalytic activation of this difficult electrophile with predictable stereo-outcomes presents an even more formidable challenge. Described herein is a simple iron-based catalyst system which provides the mild, direct conversion of secondary and tertiary alcohols to sulfonamides. Starting from enantioenriched alcohols, the intramolecular variant proceeds with stereoinversion to produce enantioenriched 2- and 2,2-subsituted pyrrolidines and indolines, without prior derivatization of the alcohol or solvolytic conditions.

Organocatalytic Enantioselective Acyloin Rearrangement of α-Hydroxy Acetals to α-Alkoxy Ketones

We report an unprecedented organocatalytic enantioselective acyloin rearrangement of α,α-disubstituted α-hydroxy acetals. In the presence of a catalytic amount of chiral binol-derived N-triflyl phosphoramide, α-hydroxy acetals rearranged to α-alkoxy ketones in good to high yields with high enantioselectivities. Formation of an ion pair between the in situ generated oxocarbenium ion and the chiral phosphoramide anion was proposed to be responsible for the highly efficient transfer of chirality. Conditions for removal of cyclohexyl and cyclopentyl groups from the corresponding α-alkoxy ketones were uncovered underpinning their potential general utility as hydroxy protecting groups. Conversion of the rearranged products to the enantioenriched α-hydroxy ketone, 1,2-diol, β-amino alcohol and 1,4-dioxane was also documented.

Collective Synthesis of cladiellins based on the gold-catalyzed cascade reaction of 1,7-diynes

The cladiellin family of natural products, which includes molecules with various biological activities, continues to invite new synthetic studies. A gold-catalyzed tandem reaction of 1,7-diynes to construct the 6-5-bicyclic ring systems that are present in a number of natural products was developed. This reaction was applied as the key step to realize the formal and total syntheses of nine members of the cladiellin family in an enantio- and diastereoselective manner. This modular and efficient approach could also be used for the construction of other cladiellins, as well as their analogues, for follow-up studies. Clad(iellins) in gold: A gold-catalyzed tandem reaction of 1,7-diynes was previously developed to construct the 6-5-bicyclic ring systems that are present in a number of natural products. This reaction was applied to realize the total synthesis of nine members of the cladiellin family. This modular and efficient approach, which is enantio- and stereoselective, could also be used for the construction of other cladiellins and their analogues. Copyright

A simple, scalable synthetic route to (+)- and (-)-pseudoephenamine

A three-step synthesis of pseudoephenamine suitable for preparing multigram amounts of both enantiomers of the auxiliary from the inexpensive starting material benzil is described. The sequence involves synthesis of the crystalline monomethylimine derivat

Synthesis of quaternary α-methyl α-amino acids by asymmetric alkylation of pseudoephenamine alaninamide pivaldimine

The utility of pseudoephenamine as a chiral auxiliary for the alkylative construction of quaternary α-methyl α-amino acids is demonstrated. The method is notable for the high diastereoselectivities of the alkylation reactions, for its versatility with respect to electrophilic substrate partners, and for its mild hydrolysis conditions, which provide α-amino acids without salt contaminants. Alternatively, α-amino esters can be obtained by direct alcoholysis.

Pseudoephenamine: A practical chiral auxiliary for asymmetric synthesis

Unrestricted: Pseudoephenamine is introduced as a versatile chiral auxiliary and an alternative to pseudoephedrine in asymmetric synthesis. It is free from regulatory restrictions and leads to remarkable stereocontrol in alkylation reactions, especially in those that form quaternary carbon centers. Amides derived from pseudoephenamine exhibit a high propensity to be crystalline substances, and provide sharp, well-defined signals in NMR spectra. Copyright

A concise and versatile double-cyclization strategy for the highly stereoselective synthesis and arylative dimerization of aspidosperma alkaloids

Building cycles: A strategy for the concise, stereoselective synthesis of aspidosperma alkaloids and related structures via a common putative diiminium ion intermediate is reported. The approach enables the dimerization of aspidosperma-type structures at the sterically hindered C2 position. The intermediate is prepared in one step from the shown lactam through an electrophilic double-cyclization cascade (see scheme; Tf= trifluoromethanesulfonyl). Copyright

Aminophosphine phosphinites derived from chiral 1,2-diphenyl-2-aminoethanols: Synthesis and application in rhodium-catalyzed asymmetric hydrogenation of dehydroamino acid derivatives

A series of chiral aminophosphine phosphinites DPAMPPs was synthesized from optically active 1,2-diphenyl-2-aminoethanols. The erythro-DPAMPPs were found to serve as excellent ligands for rhodium-catalyzed asymmetric hydrogenation of dehydroamino acid derivatives. For an array of dehydroamino acid precursors, remarkably high enantioselectivity (up to 98.4% e.e.) and reactivity (the ratio of substrate/catalyst up to 10000) were observed. Some factors controlling the enantioselectivity were examined and discussed. (C) 2000 Elsevier Science Ltd.