IroMycin A

Base Information

• Chemical Name: IroMycin A
• CAS No.: 213137-53-2
• Molecular Formula: C19H29NO2
• Molecular Weight: 303.43906
• Mol file: 213137-53-2.mol

Synonyms:IroMycin A;6-[(2E,5E)-3,7-Dimethyl-2,5-octadienyl]-4-hydroxy-3-methyl-5-propyl-2(1H)-pyridinone;NK 26588

Chemical Property of IroMycin A

Chemical Property:

• PSA: 53.09000
• LogP: 4.43250

Purity/Quality:

98% ^*data from raw suppliers

Iromycin A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of IroMycin A

There total 9 articles about IroMycin A 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%

4-benzoyloxy-6-[(E,E)-3,7-dimethylocta-2,5-dienyl]-3-methyl-5-propylpyran-2-one (945952-32-9) → iromycin A (213137-53-2)

Guidance literature:

With ammonia; at 70 ℃; for 48h;

DOI:10.1021/jo070327j

Reference yield:

2-acetylpropanoic acid ethyl ester (609-14-3) → iromycin A (213137-53-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 56 percent / LDA / hexane; tetrahydrofuran / 2.5 h / 0 °C

2.1: LDA / cyclohexane; tetrahydrofuran / 2 h / -78 °C

3.1: 9.71 g / DBU / benzene / 6 h / Heating

4.1: 89 percent / pyridine / 44 h / 20 °C

5.1: 99 percent / SeO₂ / dioxane / 21 h / 130 °C

6.1: 91 percent / NaBH₄ / ethanol / 4 h / 20 °C

7.1: 99 percent / PBr₃ / dioxane / 15.5 h

8.1: nBuLi / hexane; tetrahydrofuran / 0.5 h / 0 °C

8.2: 95 percent / hexane; tetrahydrofuran / 2 h / 0 °C

9.1: 65 percent / liquid NH₃ / 48 h / 70 °C

With pyridine; sodium tetrahydroborate; n-butyllithium; selenium(IV) oxide; ammonia; phosphorus tribromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; ethanol; hexane; cyclohexane; benzene;

DOI:10.1021/jo070327j

Reference yield:

ethyl 4-acetyl-2-methyl-3-oxoheptanoate (945952-11-4) → iromycin A (213137-53-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 9.71 g / DBU / benzene / 6 h / Heating

2.1: 89 percent / pyridine / 44 h / 20 °C

3.1: 99 percent / SeO₂ / dioxane / 21 h / 130 °C

4.1: 91 percent / NaBH₄ / ethanol / 4 h / 20 °C

5.1: 99 percent / PBr₃ / dioxane / 15.5 h

6.1: nBuLi / hexane; tetrahydrofuran / 0.5 h / 0 °C

6.2: 95 percent / hexane; tetrahydrofuran / 2 h / 0 °C

7.1: 65 percent / liquid NH₃ / 48 h / 70 °C

With pyridine; sodium tetrahydroborate; n-butyllithium; selenium(IV) oxide; ammonia; phosphorus tribromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; 1,4-dioxane; ethanol; hexane; benzene;

DOI:10.1021/jo070327j

upstream raw materials:

4-benzoyloxy-6-[(E,E)-3,7-dimethylocta-2,5-dienyl]-3-methyl-5-propylpyran-2-one

2-acetylpropanoic acid ethyl ester

ethyl 4-acetyl-2-methyl-3-oxoheptanoate

4-hydroxy-3,6-dimethyl-5-propylpyran-2-one

Refernces