(R)-6-(iodomethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-one

Base Information

• Chemical Name: (R)-6-(iodomethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-one
• CAS No.: 1370729-72-8
• Molecular Formula: C₁₃H₁₅IO₃
• Molecular Weight: 346.165
• Mol file: 1370729-72-8.mol

Synonyms:(R)-6-(iodomethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-one

Chemical Property of (R)-6-(iodomethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-6-(iodomethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-one

There total 4 articles about (R)-6-(iodomethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-one 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: 65.0%

5-(4-methoxyphenyl)hex-5-enoic acid (1258204-03-3) → (S)-6-(iodomethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-one (1258203-95-0) + (R)-6-(iodomethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-one (1370729-72-8)

Guidance literature:

With N-iodo-succinimide; C₄₅H₄₈N₂O₃Zn₂; In toluene; at -40 ℃; enantioselective reaction;

DOI:10.1016/j.tetlet.2013.11.028

Reference yield:

5-(4-methoxyphenyl)-5-oxopentanoic acid (4609-10-3) → (S)-6-(iodomethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-one (1258203-95-0) + (R)-6-(iodomethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-one (1370729-72-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: acetyl chloride / 0 - 20 °C

2.1: tetrahydrofuran; toluene / -78 - 0 °C

2.2: -78 - 20 °C

3.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 °C

4.1: N-iodo-succinimide; iodine; 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((1R,2R)-2-(dipentylamino)cyclohexyl)amino)cyclobut-3-ene-1,2-dione / acetone; dichloromethane / 24 h / -78 °C

With N-iodo-succinimide; lithium hydroxide monohydrate; 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((1R,2R)-2-(dipentylamino)cyclohexyl)amino)cyclobut-3-ene-1,2-dione; water; iodine; acetyl chloride; In tetrahydrofuran; dichloromethane; acetone; toluene;

DOI:10.1021/ol302798g

Reference yield:

5-(4-methoxy-phenyl)-5-oxo-pentanoic acid methyl ester (1847-68-3) → (S)-6-(iodomethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-one (1258203-95-0) + (R)-6-(iodomethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-2-one (1370729-72-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrahydrofuran; toluene / -78 - 0 °C

1.2: -78 - 20 °C

2.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 °C

3.1: N-iodo-succinimide; iodine; 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((1R,2R)-2-(dipentylamino)cyclohexyl)amino)cyclobut-3-ene-1,2-dione / acetone; dichloromethane / 24 h / -78 °C

With N-iodo-succinimide; lithium hydroxide monohydrate; 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((1R,2R)-2-(dipentylamino)cyclohexyl)amino)cyclobut-3-ene-1,2-dione; water; iodine; In tetrahydrofuran; dichloromethane; acetone; toluene;

DOI:10.1021/ol302798g

upstream raw materials:

5-(4-methoxyphenyl)hex-5-enoic acid

5-(4-methoxyphenyl)-5-oxopentanoic acid

5-(4-methoxy-phenyl)-5-oxo-pentanoic acid methyl ester

5-(4-methoxyphenyl)hex-5-enoic acid methyl ester