Villalstonine

Base Information

• Chemical Name: Villalstonine
• CAS No.: 2723-56-0
• Molecular Formula: C₄₁H₄₈N₄O₄
• Molecular Weight: 660.857
• NSC Number: 222838
• DSSTox Substance ID: DTXSID801336397
• Wikipedia: Villalstonine
• Wikidata: Q15427939

Synonyms:villalstonine

Chemical Property of Villalstonine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.47g/cm³
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 660.36755603
• Heavy Atom Count: 49
• Complexity: 1440

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C1CN2CCC34CC5C6CC7C8=C(CC(C6COC5(OC39C2CC1C(N9C1=CC=CC=C41)C(=O)OC)C)N7C)C1=CC=CC=C1N8C
• Isomeric SMILES: C/C=C/1\CN2CCC34CC5C6CC7C8=C(CC(C6COC5(OC39C2CC1C(N9C1=CC=CC=C41)C(=O)OC)C)N7C)C1=CC=CC=C1N8C

Technology Process of Villalstonine

There total 17 articles about Villalstonine 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: 41.0%

pleiocarpamine (6393-66-4,60325-74-8,80249-86-1) + (+)-macroline (2269-93-4) → villalstonine (2723-56-0)

Guidance literature:

With hydrogenchloride; at 22 ℃; for 24h;

DOI:10.1021/ja00099a021

Reference yield:

C23H25N2O(1+)*CF3O3S(1-) → villalstonine (2723-56-0)

Guidance literature:

Multi-step reaction with 14 steps

1: H₂ / 10percent Pd/C / aq. ethanol / 760 Torr

2: 1.) LDA, 3.) aq. KOH

3: 84 percent / LiClO₄, PO(Bu)3 / toluene / 2 h / Heating

4: 90 percent / LiAlH₄ / diethyl ether / 2 h / -20 °C

5: 92 percent / Et₃N / dioxane / 72 h / Ambient temperature

6: 65 percent / benzene / 20 h / 145 °C

7: 86 percent / NaBH₃ / ethanol / 18 h / Ambient temperature

8: 94 percent / p-TsOH / 24 h / Ambient temperature

9: 1.) 9-BBN, 2.) aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 22 deg C, 25 h, 2.) THF, 45 deg C, 2.5 h

10: 99 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 18 h / Ambient temperature

11: 90 percent / PTSA / methanol / 5 h / 22 °C

12: 1.) Ac₂O, pyridine, 2.) pyridinium dichromate / 1.) CH₂Cl₂, RT, 27 h, 2.) CH₂Cl₂, 8 h

13: 83 percent / Bu₄NF / tetrahydrofuran / 5 h / Ambient temperature

14: 41 percent / 0.2 N aq. HCl / 24 h / 22 °C

With pyridine; hydrogenchloride; dmap; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; dipyridinium dichromate; 9-borabicyclo[3.3.1]nonane dimer; Tributylphosphine oxide; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; lithium perchlorate; acetic anhydride; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; toluene; benzene;

DOI:10.1021/ja00099a021

Reference yield:

(6S,10S)-(-)-5,12-dimethyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole (126790-59-8) → villalstonine (2723-56-0)

Guidance literature:

Multi-step reaction with 13 steps

1: 1.) LDA, 3.) aq. KOH

2: 84 percent / LiClO₄, PO(Bu)3 / toluene / 2 h / Heating

3: 90 percent / LiAlH₄ / diethyl ether / 2 h / -20 °C

4: 92 percent / Et₃N / dioxane / 72 h / Ambient temperature

5: 65 percent / benzene / 20 h / 145 °C

6: 86 percent / NaBH₃ / ethanol / 18 h / Ambient temperature

7: 94 percent / p-TsOH / 24 h / Ambient temperature

8: 1.) 9-BBN, 2.) aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 22 deg C, 25 h, 2.) THF, 45 deg C, 2.5 h

9: 99 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 18 h / Ambient temperature

10: 90 percent / PTSA / methanol / 5 h / 22 °C

11: 1.) Ac₂O, pyridine, 2.) pyridinium dichromate / 1.) CH₂Cl₂, RT, 27 h, 2.) CH₂Cl₂, 8 h

12: 83 percent / Bu₄NF / tetrahydrofuran / 5 h / Ambient temperature

13: 41 percent / 0.2 N aq. HCl / 24 h / 22 °C

With pyridine; hydrogenchloride; dmap; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; dipyridinium dichromate; 9-borabicyclo[3.3.1]nonane dimer; Tributylphosphine oxide; tetrabutyl ammonium fluoride; dihydrogen peroxide; lithium perchlorate; acetic anhydride; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; toluene; benzene;

DOI:10.1021/ja00099a021

upstream raw materials:

pleiocarpamine

(+)-macroline

(6S,10S)-(-)-5,12-dimethyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

(6S,10S)-(-)-5,12-dimethyl-9-formyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole

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