(R)-(+)-Atenolol

Base Information

• Chemical Name: (R)-(+)-Atenolol
• CAS No.: 56715-13-0
• Molecular Formula: C14H22 N2 O3
• Molecular Weight: 266.34
• Hs Code.: 2924299090
• UNII: YG132I00WY
• DSSTox Substance ID: DTXSID0045753
• Nikkaji Number: J264.928D
• Wikidata: Q27095897
• Metabolomics Workbench ID: 58791
• ChEMBL ID: CHEMBL1230004
• Mol file: 56715-13-0.mol

Synonyms:(R)-(+)-Atenolol;(R)-Atenolol;56715-13-0;(+)-Atenolol;R(+)-Atenolol;Atenolol, (+)-;(R)-2-(4-(2-Hydroxy-3-(isopropylamino)propoxy)phenyl)acetamide;R-(+)-Atenolol;UNII-YG132I00WY;YG132I00WY;DTXSID0045753;CHEBI:55352;Prenormin;Benzeneacetamide, 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-, (R)-;DTXCID8025753;Vasaten;2-{4-[(2R)-2-hydroxy-3-[(propan-2-yl)amino]propoxy]phenyl}acetamide;2-[4-({(2R)2-hydroxy-3-[(propan-2-yl)amino]propyl}oxy)phenyl]acetamide;SMR000326747;(+)-(R)-Atenolol;SR-01000075276;RS-atenolol;Benzeneacetamide, 4-[(2R)-2-hydroxy-3-[(1-methylethyl)amino]propoxy]-;BENZENEACETAMIDE, 4-((2R)-2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)-;NCGC00093636-03;2TN;atenolol-(+);CAS-56715-13-0;MFCD00074917;atenolol-(+/-);Prestwick0_000953;Prestwick1_000953;Prestwick2_000953;Prestwick3_000536;ATENOLOL, (R)-;Lopac0_000146;SCHEMBL18120;BSPBio_000551;2-(4-(2-Hydroxy-3-(Isopropylamino)propoxy)phenyl)ethanamide;MLS001332497;MLS001332498;MLS002154070;BIDD:GT0478;SPBio_003095;BPBio1_000607;CHEMBL1230004;(R)-(+)-Atenolol, 99%;HMS1570P08;HMS2096L13;HMS2235G14;HMS3713L13;HY-B2111;Tox21_111211;2-[4-[(2R)-2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]acetamide;GEO-02767;AKOS017343045;Tox21_111211_1;CCG-204241;DB06987;GS-0675;NCGC00015007-14;NCGC00093636-04;NCGC00093636-05;A-142;AB00513974;CS-0020257;EU-0100146;H11709;AB00513974_06;EN300-24409966;J-200025;SR-01000075276-1;SR-01000075276-2;BRD-K68075732-001-03-5;Q27095897;(R)-(+)-ATENOLOL;(R)-ATENOLOL;(+)-ATENOLOL

Chemical Property of (R)-(+)-Atenolol

Chemical Property:

• Vapor Pressure: 3.82E-11mmHg at 25°C
• Melting Point: 148-152 °C(lit.)
• Boiling Point: 508°Cat760mmHg
• PKA: 13.88±0.20(Predicted)
• Flash Point: 261.1°C
• PSA: 84.58000
• Density: 1.125g/cm³
• LogP: 1.54330
• Solubility.: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: >6.0 m
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 266.16304257
• Heavy Atom Count: 19
• Complexity: 263

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-Atenolol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)NCC(COC1=CC=C(C=C1)CC(=O)N)O
• Isomeric SMILES: CC(C)NC[C@H](COC1=CC=C(C=C1)CC(=O)N)O
• Description: (+)-Atenolol is an enantiomer of the β1-adrenergic receptor (β1-AR) antagonist (±)-atenolol . (+)-Atenolol inhibits radioligand binding to β-ARs on sarcolemma-enriched membranes (Ki = 8.61 μM). Unlike (–)-atenolol and (±)-antenolol, (+)-atenolol has no effect on blood pressure in spontaneously hypertensive rats.

Technology Process of (R)-(+)-Atenolol

There total 23 articles about (R)-(+)-Atenolol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

isopropylamine (75-31-0) + (R)-2-(4-(3-chloro-2-hydroxypropoxy)phenyl)acetamide → (+)-(R)-atenolol (56715-13-0)

Guidance literature:

In water; at 10 ℃; for 12h;

DOI:10.1039/c4ra16365f

Reference yield: 70.0%

(R)-1-phenoxy>-3-(isopropylamino)propan-2-ol (143925-25-1) → (+)-(R)-atenolol (56715-13-0)

Guidance literature:

With ammonium hydroxide; In methanol; Ambient temperature;

DOI:10.1021/jo00048a040

Reference yield:

Isopropenyl acetate (108-22-5) + (RS)-atenolol (29122-68-7) → C16H24N2O4 + (+)-(R)-atenolol (56715-13-0) + (S)-Atenolol (93379-54-5)

Guidance literature:

With Candida rugosa lipase OF immobilized onto Fe₃O₄-CS-Et-(NH₂)₃ magnetic nanoparticles; In toluene; at 35 ℃; for 240h; Reagent/catalyst; Time; enantioselective reaction; Resolution of racemate; Enzymatic reaction;

DOI:10.1016/j.tetasy.2017.01.012

upstream raw materials:

(R)-1-phenoxy>-3-(isopropylamino)propan-2-ol

(S)-epichlorohydrin

2-(4-hydroxyphenyl)acetamide

isopropylamine

Refernces

• 1、 Kitaori, Kazuhiro,Takehira, Yosikazu,Furukawa, Yoshiro,Yoshimoto, Hiroshi,Otera, Junzo. "Convenient preparation of enantiopure atenolol by means of preferential crystallization". . p. 505 - 507. Retrieved 1998.
• 2、 Shuang, Yazhou,Liao, Yuqin,Wang, Hui,Wang, Yuanxing,Li, Laisheng. "Preparation and evaluation of a triazole-bridged bis(β-cyclodextrin)–bonded chiral stationary phase for HPLC". . p. 168 - 184. Retrieved 2019/11/25.
• 3、 Li, Yingjie,Tang, Yimin,Qin, Shili,Li, Xue,Dai, Qiang,Gao, Lidi. "Preparation and characterization of a new open-tubular capillary column for enantioseparation by capillary electrochromatography". . p. 283 - 292. Retrieved 2019/02/05.