Trimethoquinol

Base Information

• Chemical Name: Trimethoquinol
• CAS No.: 18559-59-6
• Molecular Formula: C19H23 N O5 . Cl H
• Molecular Weight: 381.856
• European Community (EC) Number: 242-423-5
• UNII: 298SP836N4
• DSSTox Substance ID: DTXSID1048756
• ChEMBL ID: CHEMBL1788290
• Mol file: 18559-59-6.mol

Synonyms:AQ 110;AQ-110;AQ110;AQL 208;AQL-208;AQL208;CV 705;CV-705;CV705;Tetroquinol;Tretoquinol;Tretoquinol Hydrochloride;Tretoquinol Hydrochloride Anhydrous;Tretoquinol Hydrochloride, (S)-Isomer;Tretoquinol-(R);Tretoquinol-(S) HCl;Trimethoquinol;Trimetoquinol

Chemical Property of Trimethoquinol

Chemical Property:

• Vapor Pressure: 6.29E-13mmHg at 25°C
• Boiling Point: 533.3°Cat760mmHg
• Flash Point: 276.3°C
• PSA: 80.18000
• Density: 1.235g/cm³
• LogP: 3.68390
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 381.1343006
• Heavy Atom Count: 26
• Complexity: 409

Purity/Quality:

99%, ^*data from raw suppliers

S-(-)-TretoquinolHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1OC)OC)CC2C3=CC(=C(C=C3CCN2)O)O.Cl
• Isomeric SMILES: COC1=CC(=CC(=C1OC)OC)C[C@H]2C3=CC(=C(C=C3CCN2)O)O.Cl
• Uses: S-(-) S-(-)-Tretoquinol belongs to the class of adrenergic inhalants, selective β-2-adrenoreceptor agonists. S-(-)-Tretoquinol is used in the treatment of obstructive airway diseases. S-(-)-Tretoquinol is a bronchodilator.

Technology Process of Trimethoquinol

There total 10 articles about Trimethoquinol 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: 96.0%

(S)-6,7-Bis(benzyloxy)-1-<(3,4,5-trimethoxyphenyl)methyl>-1,2,3,4-tetrahydroisoquinoline hydrochloride → (-)-Trimetoquinol hydrochloride (18559-59-6,18559-60-9,14187-92-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 50 ℃; for 16h; under 3040 Torr;

DOI:10.1021/jo00081a007

Reference yield: 86.0%

(1S,1'S)-6,7-dibenzyloxy-2-(2-hydroxy-1-phenylethyl)-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline → (-)-Trimetoquinol hydrochloride (18559-59-6,18559-60-9,14187-92-9)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1248/cpb.39.1126

Reference yield:

(3S)-8,9-dibenzyloxy-3-phenyl-2,3,5,6-tetrahydro-10bH-oxazolo-<2,3-a>isoquinoline → (-)-Trimetoquinol hydrochloride (18559-59-6,18559-60-9,14187-92-9)

Guidance literature:

Multi-step reaction with 2 steps

2: 86 percent / H₂, 10percent HCl / 10percent Pd-C / ethanol

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1248/cpb.39.1126

upstream raw materials:

5-(chloromethyl)-1,2,3-trimethoxybenzene

3-hydroxy-4-(methoxymethoxy)benzaldehyde

3,4-dihydroxybenzaldehyde

Refernces

• 1、 Kitamura,Hsiao,Ohta,Tsukamoto,Ohta,Takaya,Noyori. "General asymmetric synthesis of isoquinoline alkaloids. Enantioselective hydrogenation of enamides catalyzed by BINAP-ruthenium(II) complexes". . p. 297 - 310. Retrieved 2007/10/02.