79868-78-3

Basic information

• Product Name: (S)-(-)-2-AMINO-1,1,3-TRIPHENYL-1-PROPANOL
• Synonyms: (S)-(-)-2-AMINO-1,1,3-TRIPHENYL-1-PROPANOL;(2S)-1,1,3-Triphenyl-2-amino-1-propanol;(S)-1,1,3-Triphenyl-2-amino-1-propanol;(S)-2-Amino-1,1,3-triphenyl-1-propanol,99%e.e.
• CAS NO: 79868-78-3
• Molecular Formula: C₂₁H₂₁NO
• Molecular Weight: 303.4
• Product Categories: Amino Alcohols;Chiral Building Blocks;Organic Building Blocks
• Mol File: 79868-78-3.mol

Chemical Properties

• Melting Point: 139-144 °C(lit.)
• Boiling Point: 502.3 °C at 760 mmHg
• Flash Point: 257.6 °C
• Appearance: /
• Density: 1.145 g/cm³
• Vapor Pressure: 6.57E-11mmHg at 25°C
• Refractive Index: 1.627
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (S)-(-)-2-AMINO-1,1,3-TRIPHENYL-1-PROPANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-2-AMINO-1,1,3-TRIPHENYL-1-PROPANOL(79868-78-3)
• EPA Substance Registry System: (S)-(-)-2-AMINO-1,1,3-TRIPHENYL-1-PROPANOL(79868-78-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 79868-78-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(S)-(-)-2-AMINO-1,1,3-TRIPHENYL-1-PROPANOL is used as a chiral auxiliary for controlling the stereochemistry of reactions, ensuring the production of enantiomerically pure compounds. This is crucial in the synthesis of complex organic molecules with specific biological activities.
Used in Asymmetric Catalysis:
In the pharmaceutical and fine chemical industries, (S)-(-)-2-AMINO-1,1,3-TRIPHENYL-1-PROPANOL serves as a chiral ligand in asymmetric catalysis. Its role is to facilitate the synthesis of enantiomerically pure compounds, which are essential for the development of effective and safe drugs.
Used in Drug Discovery:
(S)-(-)-2-AMINO-1,1,3-TRIPHENYL-1-PROPANOL is utilized in drug discovery for its potential to create novel compounds with specific biological targets. Its stereochemical properties allow for the design of molecules with high selectivity, leading to more effective treatments with fewer side effects.
Used in Medicinal Chemistry:
In medicinal chemistry, (S)-(-)-2-AMINO-1,1,3-TRIPHENYL-1-PROPANOL is employed to develop new pharmaceutical agents with improved efficacy and selectivity. Its unique structure enables the creation of compounds that can interact with biological targets in a highly specific manner.
Used in Materials Science:
(S)-(-)-2-AMINO-1,1,3-TRIPHENYL-1-PROPANOL also finds applications in materials science, where its stereochemistry can be exploited to design new materials with tailored properties, such as chiral polymers and other advanced materials with specific optical, electronic, or mechanical characteristics.

InChI:InChI=1/C21H21NO/c22-20(16-17-10-4-1-5-11-17)21(23,18-12-6-2-7-13-18)19-14-8-3-9-15-19/h1-15,20,23H,16,22H2/t20-/m0/s1

Upstream product

• 63-91-2 L-phenylalanine 
• 108-86-1 bromobenzene 
• 3182-93-2 (L)-phenylalanine ethyl ester hydrochloride 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 3081-24-1 H-Phe-OEt 
• 100-58-3 phenylmagnesium bromide 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 57728-37-7 DL-2-Amino-1,1,3-triphenyl-1-propanol 
• 673-06-3 D-(R)-phenylalanine 
• 21685-51-8 D-phenylalanine methyl ester 
• 13033-84-6 D-phenylalanine methyl ester hydrochloride 
• 87877-11-0 Phe-Chlor 

Downstream Products

• 206264-60-0 (4S,8R,11S)-(-)-11-Benzyl-10,10-diphenyl-9-oxa-1-azatricyclo[6.3.0.0^4,8]undecan-2-one 
• 191090-38-7 (S)-(-)-5-benzyl-4,4-diphenyl-1,3-oxazolidinone 
• 191274-50-7 (S)-4,4-diphenyl-5-benzyloxazolidin-2-thione 

Relevant articles and documents

Simple primary β-amino alcohols as organocatalysts for the asymmetric Michael addition of β-keto esters to nitroalkenes

Simple primary β-amino alcohols act as an efficient organocatalysts in the asymmetric Michael addition of β-keto esters with nitroalkenes affording highly pure chiral Michael adducts. Also, both enantiomers of the adducts were obtained, depending on the specific catalyst used and reaction temperature.

Catalytic intramolecular hydroamination of aminoallenes using titanium complexes of chiral, tridentate, dianionic imine-diol ligands

Alkylation of d- or l-phenylalanine or valine alkyl esters was carried out using methyl or phenyl Grignard reagents. Subsequent condensation with salicylaldehyde, 3,5-di-tert-butylsalicylaldehyde, or 5-fluorosalicylaldehyde formed tridentate, X2/sub

Total Synthesis of the Marine Macrolide Amphidinolide F

A new and efficient convergent approach toward the synthesis of amphidinolide F is described through the assembly of three fragments. The two trans-tetrahydrofurans were built by a diastereoselective C-glycosylation with titanium enolate of bulky N-acetyloxazolidinethiones. The side chain was inserted by a Liebeskind-Srogl cross-coupling reaction. A sulfone condensation/desulfonylation sequence, a Stille cross-coupling, and a macrolactonization were applied to connect the fragments.

Hybrid-Type Squaramide-Fused Amino Alcohol Organocatalysts for Enantioselective Nitro-Aldol Reaction of Nitromethane with Isatins

A series of hybrid-type squaramide-fused amino alcohol (SFAA) catalysts were synthesized, and their catalytic efficiency in the enantioselective nitro-aldol reaction of various isatins with nitromethane has been described. This transformation afforded chiral 3-substituted 3-hydroxyoxindoles in excellent chemical yields (up to 99 %) with high enantioselectivities (up to 95 % ee). The resulting chiral 3-hydroxyoxindoles can be further used as synthetic precursors for the synthesis of several natural products that have a broad spectrum of fascinating biological activities.

Simple primary β-amino alcohol catalyzed enantioselective Diels-Alder reaction of 3-hydroxy-2-pyridones

The simple primary β-amino alcohol catalyzed Diels-Alder reaction of 3-hydroxy-2-pyridones as dienes with N-substituted maleimides to provide the highly substituted optically active isoquinuclidines as a single diastereomers in excellent enantioselectivities (up to 98%) with excellent chemical yields (up to 95%) was demonstrated. A range of simple β-amino alcohols were synthesized from the corresponding inexpensive amino acids and their catalytic activity was examined for this reaction.

Silyloxy Amino Alcohol Organocatalyst for Enantioselective 1,3-Dipolar Cycloaddition of Nitrones to α,β-Unsaturated Aldehydes

The catalytic activity of a simple amino alcohol that contains a bulky super silyl group [i.e., tris(trimethylsilyl)silyl (TTMSS)] bonded to the oxygen atom at the γ-position along with a primary amine moiety was examined in the enantioselective 1,3-dipolar cycloaddition of nitrones to α,β-unsaturated aldehydes. The organocatalyst successfully provided optically active isoxazolidines in good chemical yields (up to 86 %) with excellent diastereoselectivities (endo/exo, up to 96:4) and enantioselectivities (up to 97 % ee). Furthermore, the obtained isoxazolidines were easily converted into γ-amino diols that contain three contiguous stereogenic centers.

Chiral Bis(oxazolidine)pyridine-copper-catalyzed enantioselective friedel-crafts alkylation of indoles with nitroalkenes

Catalytic asymmetric Friedel-Crafts reaction of indoles with nitroalkenes was catalyzed by the stereochemically tunable bis(oxazolidine)pyridine (PyBodine)-Cu(OTf)2 complex. Using the PyBodine(Val)-Cu(OTf) 2 catalyst gave the Friedel-Crafts ?adducts with highly enantioselective manner. For the 1,4-bis[(E)-2-nitrovinyl]benzene, the reaction proceeded in a meso-trick manner to give the chiral double Friedel-Crafts adduct with 97% enantiomeric excess. Georg Thieme Verlag Stuttgart New York.

Efficient asymmetric addition of diethylzinc to aldehydes using C 2-novel chiral pyridine β-amino alcohols as chiral ligands

A series of novel C2-symmetric chiral pyridine β-amino alcohol ligands have been synthesized from 2,6-pyridine dicarboxaldehyde, m-phthalaldehyde and chiral β-amino alcohols through a two-step reaction. All their structures were characterized by 1H NMR, 13C NMR and IR. Their enantioselective induction behaviors were examined under different conditions such as the structure of the ligands, reaction temperature, solvent, reaction time and catalytic amount. The results show that the corresponding chiral secondary alcohols can be obtained with high yields and moderate to good enantiomeric excess. The best result, up to 89% ee, was obtained when the ligand 3c (2S,2R)-2,2-((pyridine-2,6-diylbis(methylene)) bisazanediyl))bis(4-methyl-1,1-diphenylpentan-1-ol) was used in toluene at room temperature. The ligand 3g (2S,2R)-2,2-((1,3-phenylenebis(methylene)) bis(azanediyl))bis(4-methyl-1,1-diphenylpentan-1-ol) was prepared in which the pyridine ring was replaced by the benzene ring compared to 3c in order to illustrate the unique role of the N atom in the pyridine ring in the inductive reaction. The results indicate that the coordination of the N atom of the pyridine ring is essential in the asymmetric induction reaction. Copyright

Asymmetric epoxidation of chalcones promoted by chiral schiff bases and amino alcohols

A series of chiral ligands were conveniently prepared from L-phenylalanine and characterized. Their application to the asymmetric epoxidation of chalcone was studied. The results demonstrated that 3a were efficient catalysts for enantioselective epoxidation of chalcone in moderate yield (up to 58.6%) and high enantioselectivities (up to 90% e.e.).

Asymmetric Henry reaction catalyzed by Cu(I)-based chiral amino alcohol complex

The Cu(I)-based complex prepared from (S)-2-(furan-2-yl-methylamino)-2- phenylethanol (5c) and CuCl was used as catalyst in enantioselective Henry reactions of arylaldehydes and nitromethane, which gave 89% ee and 95% yield at ambient temperature. The proposed catalytic cycle of an asymmetric Henry reaction was suggested. TUeBITAK.