Vallesine

Base Information

• Chemical Name: Vallesine
• CAS No.: 466-46-6
• Molecular Formula: C21H28N2O2
• Molecular Weight: 340.4592
• UNII: 53OB0BOS97
• DSSTox Substance ID: DTXSID10196882
• Nikkaji Number: J661.702F
• Wikidata: Q27261118
• Mol file: 466-46-6.mol

Synonyms:Vallesine;UNII-53OB0BOS97;Aspidospermidine-1-carboxaldehyde, 17-methoxy-;53OB0BOS97;466-46-6;DTXSID10196882;N-DEACETYL-N-FORMYLASPIDOSPERMINE;N-FORMYL-N-DEACETYLASPIDOSPERMINE;N-FORMYL-N-DEACETYLASPIDOSPERMINE [MI];Q27261118

Chemical Property of Vallesine

Chemical Property:

• Vapor Pressure: 3.71E-10mmHg at 25°C
• Boiling Point: 500.7°Cat760mmHg
• Flash Point: 256.6°C
• Density: 1.22g/cm³
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 340.215078140
• Heavy Atom Count: 25
• Complexity: 554

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC12CCCN3C1C4(CC3)C(CC2)N(C5=C4C=CC=C5OC)C=O
• Isomeric SMILES: CC[C@]12CCCN3[C@H]1[C@@]4(CC3)[C@@H](CC2)N(C5=C4C=CC=C5OC)C=O

Technology Process of Vallesine

There total 9 articles about Vallesine 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: 87.0%

formic acid (64-18-6) + (+)-deacetylaspidospermine (2447-50-9) → vallesine (466-46-6)

Guidance literature:

With acetic anhydride; at 23 ℃; for 2.25h; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.orglett.8b01428

Reference yield:

formyl acetic anhydride (2258-42-6) → vallesine (466-46-6)

Guidance literature:

With benzene;

DOI:10.1021/ja01552a042 DOI:10.1002/hlca.19480310221

Reference yield:

C25H35BN2O3 → vallesine (466-46-6)

Guidance literature:

Multi-step reaction with 5 steps

1: hydroxylamine / methanol; water / 48 h / 23 °C / Inert atmosphere

2: caesium carbonate / acetone / 4 h / 23 °C / Inert atmosphere

3: diisobutylaluminium hydride / tetrahydrofuran; hexane / 7 h / -78 °C / Inert atmosphere

4: lithium aluminium tetrahydride / tetrahydrofuran / 14.5 h / 0 - 23 °C

5: acetic anhydride / 2.25 h / 23 °C / Sealed tube; Inert atmosphere

With lithium aluminium tetrahydride; hydroxylamine; acetic anhydride; diisobutylaluminium hydride; caesium carbonate; In tetrahydrofuran; methanol; hexane; water; acetone;

DOI:10.1021/acs.orglett.8b01428

upstream raw materials:

formyl acetic anhydride

(+)-dehydrodeacetylaspidospermine

formic acid

(+)-deacetylaspidospermine