Spegazzinine

Base Information

• Chemical Name: Spegazzinine
• CAS No.: 6882-72-0
• Molecular Formula: C21H28N2O3
• Molecular Weight: 356.4586
• DSSTox Substance ID: DTXSID70988528
• Nikkaji Number: J15.610H
• Mol file: 6882-72-0.mol

Synonyms:spegazzinine

Chemical Property of Spegazzinine

Chemical Property:

• Vapor Pressure: 1.37E-14mmHg at 25°C
• Melting Point: 104.5-l06°C
• Boiling Point: 586.3°Cat760mmHg
• Flash Point: 308.4°C
• PSA: 64.01000
• Density: 1.33g/cm³
• LogP: 2.39710
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 356.20999276
• Heavy Atom Count: 26
• Complexity: 612

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC12CCCN3C1C4(CC3)C(C(C2)O)N(C5=C4C=CC=C5O)C(=O)C
• Isomeric SMILES: CC[C@]12CCCN3[C@H]1[C@@]4(CC3)[C@@H]([C@H](C2)O)N(C5=C4C=CC=C5O)C(=O)C
• Description: A further alkaloid which has been isolated from the bark of Aspidosperma chakense Spagazzini, this base forms colourless, irregular crystals from aqueous MeOH and has [α]D + 175.6° (CHC13). The ultraviolet spectrum in MeOH shows an absorption maximum at 258 mil with a shoulder at 285 mil. One phenolic and one non-phenolic hydroxyl groups are present and the alkaloid furnishes a crystalline hydrochloride which decomposes at 278-298°C. The oxalate crystal_x0002_lizes from Et20-MeOH with m.p. 2l2-4°C (dec.).

Technology Process of Spegazzinine

There total 19 articles about Spegazzinine 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:

C35H36N2O5 → C21H28N2O3 (1371593-24-6) + Spegazzinin, 3-Hydroxy-17-demethyl-(-)-aspidospermin (6882-72-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: ammonia / methanol / 3.5 h / 0 - 70 °C

2.1: pyridine; trifluoroacetic anhydride / 1,4-dioxane / 16 h / 0 - 20 °C

3.1: acetyl chloride / methanol / 0.5 h / 23 °C / Inert atmosphere

3.2: 2 h / 23 °C / Inert atmosphere

4.1: sodium tri-sec-butylborohydride / tetrahydrofuran / 2 h / 23 °C

5.1: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 16 h / 23 °C / Inert atmosphere

6.1: water; potassium carbonate / methanol / 2 h

7.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 70 °C / Reflux

8.1: palladium 10% on activated carbon; hydrogen / methanol; dichloromethane / 0.92 h / 23 °C

9.1: pyridine / 18 h / 23 °C

9.2: 2 h / Inert atmosphere

10.1: chiralcel OD / hexane; isopropyl alcohol

With pyridine; lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; ammonia; water; hydrogen; sodium tri-sec-butylborohydride; potassium carbonate; acetyl chloride; triphenylphosphine; trifluoroacetic anhydride; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; isopropyl alcohol; toluene; 5.1: Mitsunobu reaction;

DOI:10.1021/ol300599p

Reference yield:

C34H33N3O3 → C21H28N2O3 (1371593-24-6) + Spegazzinin, 3-Hydroxy-17-demethyl-(-)-aspidospermin (6882-72-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: acetyl chloride / methanol / 0.5 h / 23 °C / Inert atmosphere

1.2: 2 h / 23 °C / Inert atmosphere

2.1: sodium tetrahydroborate / tetrahydrofuran / 2 h / 23 °C

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 70 °C / Reflux

4.1: palladium 10% on activated carbon; hydrogen / methanol; dichloromethane / 0.92 h / 23 °C

5.1: pyridine / 18 h / 23 °C

5.2: 2 h / Inert atmosphere

6.1: chiralcel OD / hexane; isopropyl alcohol

With pyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; palladium 10% on activated carbon; hydrogen; acetyl chloride; In tetrahydrofuran; methanol; hexane; dichloromethane; isopropyl alcohol;

DOI:10.1021/ol300599p

Reference yield:

C34H35N3O3 → C21H28N2O3 (1371593-24-6) + Spegazzinin, 3-Hydroxy-17-demethyl-(-)-aspidospermin (6882-72-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium tetrahydroborate / tetrahydrofuran / 2 h / 23 °C

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 70 °C / Reflux

3.1: palladium 10% on activated carbon; hydrogen / methanol; dichloromethane / 0.92 h / 23 °C

4.1: pyridine / 18 h / 23 °C

4.2: 2 h / Inert atmosphere

5.1: chiralcel OD / hexane; isopropyl alcohol

With pyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; hexane; dichloromethane; isopropyl alcohol;

DOI:10.1021/ol300599p

upstream raw materials:

C₂₃H₁₉NO₂

C₂₄H₂₄N₂O

C₂₈H₂₆N₄O₂

Refernces