Dimemorfan phosphate

Base Information

• Chemical Name: Dimemorfan phosphate
• CAS No.: 36304-84-4
• Molecular Formula: C₁₈H₂₅N*H₃O₄P
• Molecular Weight: 353.398
• European Community (EC) Number: 252-958-6
• UNII: S203Y5Y1QP
• DSSTox Substance ID: DTXSID4048723
• Wikidata: Q27288466
• ChEMBL ID: CHEMBL3188434
• Mol file: 36304-84-4.mol

Synonyms:Astomin;AT 17;d-3-methyl-N-methylmorphinan;Dastosin;dimemorfan;dimemorfan phosphate;dimemorfan phosphate (1:1) salt;dimemorfan, (9alpha,13alpha,14alpha)-isomer;dinemorphan

Chemical Property of Dimemorfan phosphate

Chemical Property:

• Vapor Pressure: 1.42E-05mmHg at 25°C
• Melting Point: 267-269°
• Boiling Point: 366.9°Cat760mmHg
• Flash Point: 158.3°C
• PSA: 90.81000
• Density: 1.07g/cm³
• LogP: 2.69250
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 353.17559537
• Heavy Atom Count: 24
• Complexity: 401

Purity/Quality:

99% ^*data from raw suppliers

Dimemorfan(phosphate) 99.87% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(CC3C4C2(CCCC4)CCN3C)C=C1.OP(=O)(O)O
• Isomeric SMILES: CC1=CC2=C(C[C@H]3[C@@H]4[C@]2(CCCC4)CCN3C)C=C1.OP(=O)(O)O
• Therapeutic Function: Antitussive

Technology Process of Dimemorfan phosphate

There total 13 articles about Dimemorfan phosphate 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: 95.0%

(9α,13α,14α)-3-methylmorphinan-17-formaldehyde → Dimemorfan phosphate (36304-84-4,40678-33-9)

Guidance literature:

(9α,13α,14α)-3-methylmorphinan-17-formaldehyde; With sodium tetrahydroborate; zinc(II) chloride; In tetrahydrofuran; at 70 ℃; for 10h;

With phosphoric acid; In acetone; at 20 ℃; for 2h; Temperature;

Reference yield: 88.0%

Dimemorfan (36304-81-1,36304-82-2) → Dimemorfan phosphate (36304-84-4,40678-33-9)

Guidance literature:

With phosphoric acid; In tert-butyl methyl ether; isopropyl alcohol;

DOI:10.1080/00304948.2015.1025015

Reference yield:

(4bS,8aS,9S)-ethyl 3-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate (1079043-47-2) → Dimemorfan phosphate (36304-84-4,40678-33-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / dichloromethane / 5 h / 0 - 20 °C

2.1: bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; lithium chloride / N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere

2.2: 120 °C / Inert atmosphere

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C

4.1: phosphoric acid / tert-butyl methyl ether; isopropyl alcohol

With bis-triphenylphosphine-palladium(II) chloride; lithium aluminium tetrahydride; phosphoric acid; triethylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; dichloromethane; tert-butyl methyl ether; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1080/00304948.2015.1025015

upstream raw materials:

(4bS,8aS,9S)-ethyl 3-hydroxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate

(4bS,8aS,9S)-ethyl 3-methoxy-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene-11-carboxylate

(4bS,8aS,9S)-ethyl 3-(((trifluoromethyl)sulfonyl)oxy)-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)-phenanthrene-11-carboxylate

Dimemorfan

Refernces

• 1、 -. "Preparation method of dimemorfan phosphate". Page/Page column 0035; 0036. . Retrieved 2018/09/21.