171037-01-7

Basic information

• Product Name: (R)-DIPHENYLALANINOL
• Synonyms: (R)-DIPHENYLALANINOL;(R)-2-AMino-3,3-diphenylpropan-1-ol
• CAS NO: 171037-01-7
• Molecular Formula: C₁₅H₁₇NO
• Molecular Weight: 227.3
• Mol File: 171037-01-7.mol

Chemical Properties

• Boiling Point: 410.0±40.0 °C(Predicted)
• Appearance: /
• Density: 1.113±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 12.62±0.10(Predicted)
• CAS DataBase Reference: (R)-DIPHENYLALANINOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-DIPHENYLALANINOL(171037-01-7)
• EPA Substance Registry System: (R)-DIPHENYLALANINOL(171037-01-7)

Safety Data

• Hazardous Substances Data: 171037-01-7(Hazardous Substances Data)

Usage

Uses

Used in Asymmetric Synthesis:
(R)-Diphenylalaninol is used as a chiral auxiliary for enhancing the selectivity and yield of asymmetric reactions, enabling the production of enantiomerically pure compounds.
Used in Pharmaceutical Compound Preparation:
(R)-Diphenylalaninol is used as a building block in the synthesis of pharmaceutical compounds, contributing to the development of new drugs with improved efficacy and selectivity.
Used in Natural Product Derivatives:
(R)-Diphenylalaninol is used as a key component in the preparation of natural product derivatives, facilitating the synthesis of bioactive molecules with potential therapeutic applications.
Used as a Ligand in Catalysis:
(R)-Diphenylalaninol is used as a ligand in catalytic systems, enhancing the efficiency and selectivity of various chemical transformations.
Used in the Synthesis of Biologically Active Molecules:
(R)-Diphenylalaninol is used as a precursor in the synthesis of biologically active molecules, such as peptides, alkaloids, and other bioactive compounds, with potential applications in medicine and biotechnology.
Used in Anticancer Applications:
(R)-Diphenylalaninol is studied for its potential as an anti-cancer agent, with research focusing on its ability to target and inhibit the growth of cancer cells, making it a promising candidate for cancer therapy.
Used in Anti-inflammatory Applications:
(R)-Diphenylalaninol is investigated for its potential as an anti-inflammatory agent, with the aim of developing new treatments for inflammatory diseases and conditions.

Upstream product

• 204851-65-0 (R)-2-Hydroxymethyl-3,3-diphenyl-propionic acid 
• 155836-48-9 tert-butyl [(2R)-3-hydroxy-1,1-diphenylpropan-2-yl]carbamate 
• 71-43-2 benzene 
• 204851-53-6 (S)-4-Benzyl-3-((R)-2-hydroxymethyl-3,3-diphenyl-propionyl)-oxazolidin-2-one 
• 170937-75-4 (S)-N-tert-butoxycarbonyl-4-(hydroxydiphenylmethyl)-2,2-dimethyloxazolidine 

Downstream Products

• 155836-48-9 tert-butyl [(2R)-3-hydroxy-1,1-diphenylpropan-2-yl]carbamate 
• 270078-95-0 (R,R)-N,N'-bis(1-diphenylmethyl-2-hydroxyethyl)oxamide 
• 944836-33-3 (R)-4-benzhydryl-2-(2-bromophenyl)-4,5-dihydrooxazole 
• 270078-94-9 (R,R)-2,2'-isopropylidenebis(4-(diphenylmethyl)oxazoline) 
• 270078-96-1 (R,R)-N,N'-bis[2-chloro-1-(diphenylmethyl)ethyl]oxamide 
• 270078-93-8 (R,R)-N,N'-bis(2-chloro-1-(diphenylmethyl)ethyl)-2,2-dimethylmalonamide 
• 176697-24-8 [(OCH₂CH(NH₂)CH(C₆H₅)2)Al(Si(CH₃)3)2]2 
• 176697-27-1 (OCH₂CH(NH₂)CH(C₆H₅)2)Al(CH₃)2Al(CH₃)3 
• 176697-22-6 [(OCH₂CH(NH₂)CH(C₆H₅)2)Al(CH₃)2]2 
• 176697-23-7 [(OCH₂CH(NH₂)CH(C₆H₅)2)Al(C₂H₅)2]2 
• 1131379-93-5 C₂₂H₂₀INO₂ 

Relevant articles and documents

Reactions of amino alcohols in superacid: the direct observation of dicationic intermediates and their application in synthesis.

[reaction: see text]. The chemistry of amino alcohols has been studied in superacidic media, and these compounds have been found to ionize cleanly to the dication intermediates. Several dicationic species have been directly observed by low-temperature 13C NMR, including those from epinephrine (adrenaline) and synephrine. Amino alcohols react (70-99% yields) with C6H6 in triflic acid (CF3SO3H) by electrophilic aromatic substitution.

Chemo- and Enantioselective Intramolecular Silver-Catalyzed Aziridinations

Asymmetric nitrene-transfer reactions are a powerful tool for the preparation of enantioenriched amine building blocks. Reported herein are chemo- and enantioselective silver-catalyzed aminations which transform di- and trisubstituted homoallylic carbamates into [4.1.0]-carbamate-tethered aziridines in good yields and with ee values of up to 92 %. The effects of the substrate, silver counteranion, ligand, solvent, and temperature on both the chemoselectivity and ee value were explored. Stereochemical models were proposed to rationalize the observed absolute stereochemistry of the aziridines, which undergo nucleophilic ring opening to yield enantioenriched amines with no erosion in stereochemical integrity.

Bifunctional iminophosphorane organocatalysts for enantioselective synthesis: Application to the ketimine nitro-Mannich reaction

The design, synthesis, and development of a new class of modular, strongly basic, and tunable bifunctional Bronsted base/H-bond-donor organocatalysts are reported. These catalysts incorporate a triaryliminophosphorane as the Bronsted basic moiety and are readily synthesized via a last step Staudinger reaction of a chiral organoazide and a triarylphosphine. Their application to the first general enantioselective organocatalytic nitro-Mannich reaction of nitromethane to unactivated ketone-derived imines allows the enantioselective construction of β-nitroamines possessing a fully substituted carbon atom. The reaction is amenable to multigram scale-up, and the products are useful for the synthesis of enantiopure 1,2-diamine and α-amino acid derivatives.

Bisoxazoline and bioxazoline chiral ligands bearing 4-diphenylmethyl shielding substituents. Diels-Alder reaction of cyclopentadiene with 3-acryloyl-2-oxazolidinone catalyzed by the aqua nickel(II) complex

Enantiopure 2-amino-3,3-diphenyl-1-propanol was synthesized by the hidantoin route starting from diphenyl-acetaldehyde followed by subsequent functional group transformations and optical resolution by a chiral HPLC. The amino alcohol can be converted into two new chiral ligands: 4,4'-bis(diphenylmethyl)-2,2'-bioxazoline and 2,2'-isopropylidenebis(4-diphenylmethyloxazoline), and further to complexes with copper(II) trifluoromethanesulfonate and nickel(II) perchlorate hexahydrate. The nickel(II) aqua complex obtained from the bisoxazoline effectively catalyzed the Diels-Alder reactions of cyclopentadiene with 3-acryloyl-2-oxazolidinone in high endo-selectivities and moderate enantioselectivities via a square planar transition structure.

Stereocontrolled Conversion of L-Serine into a Series of Valuable Unnatural α-Amino Acids

Stereocontrolled synthesis of (2R,3S)- and (2R,3R)-phenylserine, (R)-3,3-diphenylserine and (R)-3,3-diphenylalanine are described.