14231-57-3

Basic information

• Product Name: (R)-(-)-N-BENZYL-2-PHENYLGLYCINOL
• Synonyms: (R)-(-)-N-BENZYL-2-PHENYLGLYCINOL;(2R)-2-(benzylamino)-2-phenylethanol
• CAS NO: 14231-57-3
• Molecular Formula: C₁₅H₁₇NO
• Molecular Weight: 227.3
• Product Categories: Amino Acid Derivatives;Amino Alcohols;Peptide Synthesis
• Mol File: 14231-57-3.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 87-90 °C(lit.)
• Flash Point: 136.9°C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.594
• CAS DataBase Reference: (R)-(-)-N-BENZYL-2-PHENYLGLYCINOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-N-BENZYL-2-PHENYLGLYCINOL(14231-57-3)
• EPA Substance Registry System: (R)-(-)-N-BENZYL-2-PHENYLGLYCINOL(14231-57-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 14231-57-3(Hazardous Substances Data)

Usage

Uses

Used for the asymmetric synthesis of α-amino phosphonic acids. Starting material for a practical route to optically pure β-substituted amines.

InChI:InChI=1/C15H17NO/c17-12-15(14-9-5-2-6-10-14)16-11-13-7-3-1-4-8-13/h1-10,15-17H,11-12H2/t15-/m0/s1

Upstream product

• 74879-43-9 (R)-N-benzylidene-2-hydroxy-1-phenylethylamine 
• 100-52-7 benzaldehyde 
• 1030828-76-2 N-benzyl-N-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-phenylethyl]benzenesulfonamide 
• 100-46-9 benzylamine 
• 591-51-5 phenyllithium 
• 126568-41-0 Benzyl-((1R,2S,3S)-4-benzyloxy-2,3-bis-methoxymethoxy-1-phenyl-butyl)-amine 
• 126568-43-2 Benzyl-((1R,2S,3S)-4-benzyloxy-2,3-dihydroxy-1-phenyl-butyl)-carbamic acid tert-butyl ester 
• 126568-40-9 Benzyl-[(2S,3S)-4-benzyloxy-2,3-bis-methoxymethoxy-but-(E)-ylidene]-amine 
• 126568-42-1 (1R,2S,3S)-1-Benzylamino-4-benzyloxy-1-phenyl-butane-2,3-diol 
• 98-88-4 benzoyl chloride 
• 56613-80-0 D-2-phenylglycinol 
• 875-74-1 (R)-phenylglycine 
• 216569-14-1 (2R)-2-(N-Benzylhydrazino)-2-phenylethanol 
• 862090-31-1 2-[N-benzyl-N'-(2,2,2-trifluoro-ethylidene)-hydrazino]-2-phenyl-ethanol 

Downstream Products

• 141548-84-7 1,3-oxazolidine 
• 141548-84-7 (2R,4R)-3-benzyl-4-phenyl-3-propyloxazolidine 
• 272112-23-9 N-benzyl-2-(3,4-dimethoxy-phenyl)-N-(2-hydroxy-1-phenyl-ethyl)-acetamide 
• 317820-94-3 (R)-2-[Benzyl-((E)-3-phenyl-allyl)-amino]-2-phenyl-ethanol 
• 334887-07-9 {(R)-2-[Benzyl-((R)-2-hydroxy-1-phenyl-ethyl)-carbamoyl]-1-methyl-ethyl}-phosphonic acid diethyl ester 
• 367525-88-0 {(R)-3-[Benzyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-1-methyl-propyl}-phosphonic acid diethyl ester 
• 367525-81-3 {(R)-2-[Benzyl-((R)-2-hydroxy-1-phenyl-ethyl)-carbamoyl]-1-methyl-ethyl}-phosphonic acid diisopropyl ester 

Relevant articles and documents

Enantioselective radical C–H amination for the synthesis of β-amino alcohols

Asymmetric, radical C–H functionalizations are rare but powerful tools for solving modern synthetic challenges. Specifically, the enantio- and regioselective C–H amination of alcohols to access medicinally valuable chiral β-amino alcohols remains elusive. To solve this challenge, a radical relay chaperone strategy was designed, wherein an alcohol was transiently converted to an imidate radical that underwent intramolecular H-atom transfer (HAT). This regioselective HAT was also rendered enantioselective by harnessing energy transfer catalysis to mediate selective radical generation and interception by a chiral copper catalyst. The successful development of this multi-catalytic, asymmetric, radical C–H amination enabled broad access to chiral β-amino alcohols from a variety of alcohols containing alkyl, allyl, benzyl and propargyl C–H bonds. Mechanistic experiments revealed that triplet energy sensitization of a Cu-bound radical precursor facilitates catalyst-mediated HAT stereoselectivity, enabling the synthesis of several important classes of chiral β-amines by enantioselective, radical C–H amination. [Figure not available: see fulltext.]

Green Regio- and Enantioselective Aminolysis Catalyzed by Graphite and Graphene Oxide under Solvent-Free Conditions

The ring-opening reactions of epoxides with amines were efficiently and regioselectively catalyzed by high-surface-area graphite and graphene oxide under metal-free and solvent-free conditions. For epoxides without aryl groups, catalytic activity was observed only for graphene oxide, and hence, the activity must have been due to its acidic groups. For styrene oxide, instead, graphite and graphene oxide exhibited rather similar catalytic activities, and hence, the activity was mainly due to activation of the electrophilic epoxide by π-stacking interactions with the graphitic π system. The described aminolysis procedure is green and cheap because the catalyst can be recovered and recycled without loss of efficiency. Moreover, these heterogeneous catalysts exert high stereoselective control in the presence of nonracemic epoxides and provide chiral β-amino alcohols with enantiomeric excess values up to 99 %.

Design and synthesis of enantiomeric (R)- and (S)-copper(II) and diorganotin(IV)-based antitumor agents: Their in vitro DNA binding profile, cleavage efficiency and cytotoxicity studies

New chiral reduced Schiff base ligands (R)/(S)-2-(2-hydroxy-1- phenylethylaminomethyl)phenol (L), (R)/(S)-2-(benzylamino)-2-phenylethanol (L′) and their Cu(II)/organotin(IV) complexes (1-4) were synthesized and thoroughly characterized. Preliminary in vit