tenellin

Base Information

• Chemical Name: tenellin
• CAS No.: 53823-15-7
• Molecular Formula: C₂₁H₂₃NO₅
• Molecular Weight: 369.417
• Mol file: 53823-15-7.mol

Synonyms:2(1H)-Pyridinone,3-(4,6-dimethyl-1-oxo-2,4-octadienyl)-1,4-dihydroxy-5-(4-hydroxyphenyl)-,(E,E)-; 2(1H)-Pyridinone,3-[(2E,4E)-4,6-dimethyl-1-oxo-2,4-octadienyl]-1,4-dihydroxy-5-(4-hydroxyphenyl)-(9CI); Tenellin

Chemical Property of tenellin

Chemical Property:

• Vapor Pressure: 1.95E-13mmHg at 25°C
• Boiling Point: 561.3°C at 760 mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 293.3°C
• PSA: 99.76000
• Density: 1.31g/cm³
• LogP: 3.89510

Purity/Quality:

>95% by HPLC ^*data from raw suppliers

Tenellin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Tenellin is a yellow pigment produced by species of the genus Beauveria, isolated and reported by Canadian researchers in 1968. Structure elucidation in 1977 showed that tenellin belongs to the rare 4-hydroxypyridone class containing a dienone side chain. Little has been published on the biological activity of tenellin despite the extensive use of Beauveria species, capable of producing tenellin, as biocontrol agents for agrochemical pests. Tenellin is a metabolite of the?Beauveria?species.

Technology Process of tenellin

There total 27 articles about tenellin 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: 58.0%

3-((2E,4E)-4,6-Dimethyl-octa-2,4-dienoyl)-4-hydroxy-1-(tetrahydro-pyran-2-yloxy)-5-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-1H-pyridin-2-one (81790-39-8) → tenellin (81844-67-9,53823-15-7)

Guidance literature:

With camphor-10-sulfonic acid; In methanol; benzene; for 0.333333h; Heating;

DOI:10.1021/jo00136a005

Reference yield:

4-hydroxyphenylacetate (156-38-7) → tenellin (81844-67-9,53823-15-7)

Guidance literature:

Multi-step reaction with 10 steps

1: BF₃*OEt₂ / 12 h / Ambient temperature

2: anhydrous potassium carbonate / butan-2-one / 24 h / Heating

3: 89 percent / N,N,N',N'-tetramethylethylenediamine / 12 h / 200 °C

4: 100 percent / camphorsulfonic acid (CSA) / benzene / 12 h / Heating

5: 1.) sec-BuLi / 1.) THF, -78 deg C

6: 35 percent / NaH / dimethylsulfoxide / 24 h / 22 °C

7: H₂ / 10percent Pd/C / dioxane / 0.75 h / 22 °C / 760 Torr

8: camphorsulfonic acid (CSA) / CH₂Cl₂; tetrahydrofuran / 5 h / 0 °C

9: 1.) LDA / 1.) THF, hexane, -78 deg C, 15 min, 2.) a) 30 min, b) 0 deg C, 1 h

10: 58 percent / camphorsulfonic acid (CSA) / methanol; benzene / 0.33 h / Heating

With N,N,N,N,-tetramethylethylenediamine; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen; sec.-butyllithium; sodium hydride; potassium carbonate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; butanone; benzene;

DOI:10.1021/jo00136a005

Reference yield:

(4-benzyloxy-phenyl)-acetic acid methyl ester (68641-16-7) → tenellin (81844-67-9,53823-15-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 89 percent / N,N,N',N'-tetramethylethylenediamine / 12 h / 200 °C

2: 100 percent / camphorsulfonic acid (CSA) / benzene / 12 h / Heating

3: 1.) sec-BuLi / 1.) THF, -78 deg C

4: 35 percent / NaH / dimethylsulfoxide / 24 h / 22 °C

5: H₂ / 10percent Pd/C / dioxane / 0.75 h / 22 °C / 760 Torr

6: camphorsulfonic acid (CSA) / CH₂Cl₂; tetrahydrofuran / 5 h / 0 °C

7: 1.) LDA / 1.) THF, hexane, -78 deg C, 15 min, 2.) a) 30 min, b) 0 deg C, 1 h

8: 58 percent / camphorsulfonic acid (CSA) / methanol; benzene / 0.33 h / Heating

With N,N,N,N,-tetramethylethylenediamine; camphor-10-sulfonic acid; hydrogen; sec.-butyllithium; sodium hydride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; benzene;

DOI:10.1021/jo00136a005

upstream raw materials:

3-((2E,4E)-4,6-Dimethyl-octa-2,4-dienoyl)-4-hydroxy-5-(4-hydroxy-phenyl)-1H-pyridin-2-one

3-((2E,4E)-4,6-Dimethyl-octa-2,4-dienoyl)-4-hydroxy-1-(tetrahydro-pyran-2-yloxy)-5-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-1H-pyridin-2-one

4-hydroxyphenylacetate

3-Acetyl-1,4-dihydroxy-5-(4-hydroxy-phenyl)-1H-pyridin-2-one

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