6-Iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5-epoxymorphinan

Base Information

• Chemical Name: 6-Iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5-epoxymorphinan
• CAS No.: 141392-30-5
• Molecular Formula: C₂₀H₂₄INO₃
• Molecular Weight: 453.32
• DSSTox Substance ID: DTXSID40931086
• Nikkaji Number: J496.805K
• Wikidata: Q82906612
• ChEMBL ID: CHEMBL610281
• Mol file: 141392-30-5.mol

Synonyms:6-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5-epoxymorphinan;6-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5-epoxymorphinan, ioxy epimer;6-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5-epoxymorphinan, ioxy epimer, oxalate;6-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5-epoxymorphinan, ixoy epimer, 125I-labelled;6alpha-IDCEM;6alpha-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5alpha-epoxymorphinan;6beta-IDCEM;6beta-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5alpha-epoxymorphinan

Chemical Property of 6-Iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5-epoxymorphinan

Chemical Property:

• Vapor Pressure: 6.89E-14mmHg at 25°C
• Boiling Point: 571.2°Cat760mmHg
• Flash Point: 299.3°C
• PSA: 52.93000
• Density: 1.78g/cm³
• LogP: 3.40610
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 453.08009
• Heavy Atom Count: 25
• Complexity: 585

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1CN2CCC34C5C(CCC3(C2CC6=C4C(=C(C=C6)O)O5)O)I
• Isomeric SMILES: C1C[C@]2([C@H]3CC4=C5[C@@]2(CCN3CC6CC6)[C@H]([C@H]1I)OC5=C(C=C4)O)O

Technology Process of 6-Iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5-epoxymorphinan

There total 6 articles about 6-Iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5-epoxymorphinan 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: 100.0%

3-acetoxy-6α-iodo-14-hydroxy-17-(cyclopropylmethyl)-4,5α-epoxymorphinan (141392-27-0) → 6α-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5α-epoxymorphinan (141392-30-5)

Guidance literature:

With ammonium hydroxide; In tetrahydrofuran; methanol; for 0.5h; Ambient temperature;

DOI:10.1021/jm00093a016

Reference yield:

β-naltrexol (49625-89-0) → 6α-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5α-epoxymorphinan (141392-30-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / NaHCO₃ / H₂O / 0.33 h

2: 92 percent / N-methylmorpholine / CHCl₃ / 0.17 h / -30 - -20 °C

3: 77 percent / tetraethylammonium iodide / acetonitrile / 4 h / 80 °C

4: 100 percent / conc. aq. NH₃ / tetrahydrofuran; methanol / 0.5 h / Ambient temperature

With 4-methyl-morpholine; ammonium hydroxide; tetraethylammonium iodide; sodium hydrogencarbonate; In tetrahydrofuran; methanol; chloroform; water; acetonitrile;

DOI:10.1021/jm00093a016

Reference yield:

Naltrexone (16590-41-3) → 6α-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5α-epoxymorphinan (141392-30-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / 0.533 M aq. NaOH, formamidinesulfinic acid / 1.5 h / 80 - 85 °C

2: 100 percent / NaHCO₃ / H₂O / 0.33 h

3: 92 percent / N-methylmorpholine / CHCl₃ / 0.17 h / -30 - -20 °C

4: 77 percent / tetraethylammonium iodide / acetonitrile / 4 h / 80 °C

5: 100 percent / conc. aq. NH₃ / tetrahydrofuran; methanol / 0.5 h / Ambient temperature

With 4-methyl-morpholine; ammonium hydroxide; sodium hydroxide; tetraethylammonium iodide; sodium hydrogencarbonate; formamidine; In tetrahydrofuran; methanol; chloroform; water; acetonitrile;

DOI:10.1021/jm00093a016

upstream raw materials:

3-acetoxy-6α-iodo-14-hydroxy-17-(cyclopropylmethyl)-4,5α-epoxymorphinan

β-naltrexol

Naltrexone

3-acetoxy-6β,14-dihydroxy-17-(cyclopropylmethyl)-4,5α-epoxymorphinan