Penbutolol

Base Information

• Chemical Name: Penbutolol
• CAS No.: 38363-40-5
• Deprecated CAS: 61914-98-5
• Molecular Formula: C18H29 N O2
• Molecular Weight: 291.434
• European Community (EC) Number: 253-906-5,253-074-3
• UNII: 78W62V43DY
• DSSTox Substance ID: DTXSID8023428
• Nikkaji Number: J22.286K
• Wikipedia: Penbutolol
• Wikidata: Q944244
• NCI Thesaurus Code: C66336
• Pharos Ligand ID: ZKFP9HJQWHJQ
• Metabolomics Workbench ID: 43518
• ChEMBL ID: CHEMBL87418,CHEMBL1290
• Mol file: 38363-40-5.mol

Synonyms:Betapressin;Hoe 893d;Hoe-893d;Hoe893d;Penbutolol;Penbutolol Sulfate;Penbutolol Sulfate (2:1);Sulfate, Penbutolol

Chemical Property of Penbutolol

Chemical Property:

• Vapor Pressure: 1.87E-08mmHg at 25°C
• Melting Point: 68-72°
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 438.2°Cat760mmHg
• PKA: 9.3 (1.5 mmol/l in 25% ethanol)
• Flash Point: 218.8°C
• PSA: 41.49000
• Density: 1.03g/cm³
• LogP: 3.86290
• Water Solubility.: 7g/L(room temperature)
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 291.219829168
• Heavy Atom Count: 21
• Complexity: 294

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Beta-Adrenergic Receptor Antagonists
• Canonical SMILES: CC(C)(C)NCC(COC1=CC=CC=C1C2CCCC2)O
• Isomeric SMILES: CC(C)(C)NC[C@@H](COC1=CC=CC=C1C2CCCC2)O
• Uses: Anti-adrenergic (β-receptor).
• Therapeutic Function: Beta-adrenergic blocker

Technology Process of Penbutolol

There total 15 articles about Penbutolol 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%

(S)-5-(2-cyclopentylphenoxymethyl)-3-tert-butyl-2-oxazolidinone (90970-95-9) → (S)-penbutolol (38363-40-5,38363-41-6)

Guidance literature:

With sodium hydroxide; In ethanol; water; at 73 ℃; for 8h;

Reference yield: 72.0%

tert-butylamine (75-64-9) + (R)-4-(2-Cyclopentyl-phenoxymethyl)-[1,3,2]dioxathiolane 2,2-dioxide (254430-81-4) → (S)-penbutolol (38363-40-5,38363-41-6)

Guidance literature:

tert-butylamine; (R)-4-(2-Cyclopentyl-phenoxymethyl)-[1,3,2]dioxathiolane 2,2-dioxide; In tetrahydrofuran; for 8h; Heating;

With sulfuric acid; water; In diethyl ether; for 12h;

DOI:10.1039/a902479d

Reference yield:

2-cyclopentylphenol (1518-84-9) → (S)-penbutolol (38363-40-5,38363-41-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 91 percent / K₂CO₃ / acetone / 12 h / 20 °C

2.1: 90 percent / OsO₄; K₂CO₃; H₂O / (DHQ)2PHAL; K₃Fe(CN)6 / 2-methyl-propan-2-ol / 24 h / 20 °C

3.1: 93 percent / SOCl₂; pyridine / 3 h / 0 °C

4.1: 91 percent / RuCl₃; NaIO₄ / acetonitrile; CCl₄; H₂O

5.1: tetrahydrofuran / 8 h / Heating

5.2: 72 percent / H₂SO₄; H₂O / diethyl ether / 12 h

With pyridine; ruthenium trichloride; sodium periodate; osmium(VIII) oxide; thionyl chloride; water; potassium carbonate; Hydroquinone 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III); In tetrahydrofuran; tetrachloromethane; water; acetone; acetonitrile; tert-butyl alcohol; 1.1: Alkylation / 2.1: Oxidation / 3.1: Cyclization / 4.1: Oxidation / 5.1: Substitution / 5.2: Substitution;

DOI:10.1039/a902479d

upstream raw materials:

(R)-1,2-epoxy-3-(2'-cyclopentylphenoxy)propane

tert-butylamine

(S)-1,2-epoxy-3-(2'-cyclopentylphenoxy)propane

(S)-5-(2-cyclopentylphenoxymethyl)-3-tert-butyl-2-oxazolidinone

Refernces

• 1、 -. "ANTIHYPERTENSIVE THERAPY". . . Retrieved 2009/09/08.
• 2、 Phukan, Prodeep,Sudalai, Arumugam. "Regioselective alkylation of phenol with cyclopentanol over montmorillonite K10: An efficient synthesis of l-(2-cyclopentylphenoxy)-3-[(l,l-dimethylethyl)amino]propan-2-ol {(S')-penbutolol}". . p. 3015 - 3018. Retrieved 2007/10/03.