23364-44-5 Usage
Description
(1S,2R)-2-Amino-1,2-diphenylethanol, also known as (1S,2R)-(+)-2-Amino-1,2-diphenylethanol, is a white to light yellow crystalline powder. It is an organic compound with a unique structure that features an amino group and two phenyl rings attached to a central carbon atom. (1S,2R)-2-Amino-1,2-diphenylethanol is characterized by its stereochemistry, with the S and R configurations at the first and second carbon atoms, respectively.
Uses
(1S,2R)-2-Amino-1,2-diphenylethanol is used in various applications across different industries due to its unique properties and reactivity. Here are some of its uses:
1. Used in Catalyst Preparation:
(1S,2R)-2-Amino-1,2-diphenylethanol is used as a precursor to prepare vanadium(V) Schiff base complexes. These complexes serve as catalysts in the oxidation of sulfides and olefins, which are important reactions in the chemical industry for the synthesis of various products.
2. Used in Chiral Selectors for HPLC:
(1S,2R)-2-Amino-1,2-diphenylethanol is used to prepare chiral selectors, which are then immobilized on aminated silica gel. The resulting chiral stationary phase is applied in high-performance liquid chromatography (HPLC) for the separation of enantiomers, which is crucial in pharmaceutical research and development.
3. Used in Heterogeneous Catalysis:
(1S,2R)-2-Amino-1,2-diphenylethanol can be immobilized on the frame of α-zirconium phosphate to yield layered zirconium phosphonates. These materials are used in heterogeneous catalysis, providing an alternative to homogeneous catalysts and offering advantages such as ease of separation and reuse.
4. Used as a Chiral Auxiliary in Organic Synthesis:
(1S,2R)-2-Amino-1,2-diphenylethanol is employed as a chiral auxiliary in the preparation of homopropargylic alcohols from aliphatic and aromatic aldehydes. The use of (1S,2R)-2-Amino-1,2-diphenylethanol in this context helps to control the stereochemistry of the resulting products, which is essential for the development of enantiomerically pure pharmaceuticals and other chiral compounds.
Reaction
Ligand used to make chiral oxaborolidines for the enantioselective alkynylation of aldehydes
Ligand used in organoindium reagents for asymmetric Barbier-type allylations
Ligand used in organoindium reagents for asymmetric Barbier-type propargylations
Check Digit Verification of cas no
The CAS Registry Mumber 23364-44-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,3,3,6 and 4 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 23364-44:
(7*2)+(6*3)+(5*3)+(4*6)+(3*4)+(2*4)+(1*4)=95
95 % 10 = 5
So 23364-44-5 is a valid CAS Registry Number.
InChI:InChI=1/C14H15NO/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13-14,16H,15H2/p+1/t13-,14+/m1/s1
23364-44-5Relevant articles and documents
Site-Specific C(sp3)–H Aminations of Imidates and Amidines Enabled by Covalently Tethered Distonic Radical Anions
Fang, Yuanding,Fu, Kang,Shi, Lei,Zhao, Rong,Zhou, Jia
, p. 20682 - 20690 (2020/09/07)
The utilization of N-centered radicals to synthesize nitrogen-containing compounds has attracted considerable attention recently, due to their powerful reactivities and the concomitant construction of C?N bonds. However, the generation and control of N-centered radicals remain particularly challenging. We report a tethering strategy using SOMO-HOMO-converted distonic radical anions for the site-specific aminations of imidates and amidines with aid of the non-covalent interaction. This reaction features a remarkably broad substrate scope and also enables the late-stage functionalization of bioactive molecules. Furthermore, the reaction mechanism is thoroughly investigated through kinetic studies, Raman spectroscopy, electron paramagnetic resonance spectroscopy, and density functional theory calculations, revealing that the aminations likely involve direct homolytic cleavage of N?H bonds and subsequently controllable 1,5 or 1,6 hydrogen atom transfer.
Large-scale preparation of key building blocks for the manufacture of fully synthetic macrolide antibiotics
Hogan, Philip C.,Chen, Chi-Li,Mulvihill, Kristen M.,Lawrence, Jonathan F.,Moorhead, Eric,Rickmeier, Jens,Myers, Andrew G.
, p. 318 - 325 (2018/03/21)
Key building blocks for the production of fully synthetic macrolides have been scaled-up in first time pilot plant and kilo-lab campaigns. These building blocks have supported the discovery of new macrolide antibiotics as well as ongoing preclinical studies.
Stereoretentive Addition of N-tert-Butylsulfonyl-α-Amido Silanes to Aldehydes, Ketones, α,β-Unsaturated Esters, and Imines
Mita, Tsuyoshi,Saito, Keisuke,Sugawara, Masumi,Sato, Yoshihiro
, p. 1528 - 1531 (2016/06/01)
Enantioenriched N-tert-butylsulfonyl-α-amido silanes were successfully reacted with aldehydes, ketones, imines, and α,β-unsaturated esters in the presence of a sub-stoichiometric amount of CsF (0.5 equiv) in 1,2-dimethoxyethane (DME) at -20 °C to afford the corresponding coupling products with up to 89 % enantiospecificity in a retentive manner. Keep your cool! Enantioenriched N-tert-butylsulfonyl-α-amido silanes were successfully reacted with aldehydes, ketones, imines, and α,β-unsaturated esters in the presence of a sub-stoichiometric amount of CsF (0.5 equiv) in 1,2-dimethoxyethane (DME) at -20 °C to afford the corresponding coupling products with up to 89 % enantiospecificity in a retentive manner.
