Aspidospermine

Base Information

• Chemical Name: Aspidospermine
• CAS No.: 466-49-9
• Molecular Formula: C22H30N2O2
• Molecular Weight: 354.492
• European Community (EC) Number: 207-376-7
• NSC Number: 61811,19508
• UNII: U1475W62Q5
• DSSTox Substance ID: DTXSID70196883
• Nikkaji Number: J11.323I
• Wikidata: Q27103707
• Metabolomics Workbench ID: 44350
• ChEMBL ID: CHEMBL519457
• Mol file: 466-49-9.mol

Synonyms:aspidospermine

Chemical Property of Aspidospermine

Chemical Property:

• Vapor Pressure: 7.63E-12mmHg at 25°C
• Melting Point: 208°
• Refractive Index: 1.6300 (estimate)
• Boiling Point: 542.8°Cat760mmHg
• PKA: pK1: 7.65 (25°C)
• Flash Point: 282.1°C
• PSA: 32.78000
• Density: 1.2g/cm³
• LogP: 3.72930
• Water Solubility.: 166.6mg/L(cold water)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 354.230728204
• Heavy Atom Count: 26
• Complexity: 595

Purity/Quality:

99%, ^*data from raw suppliers

ASPIDOSPERMINE 98.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of Aspidospermine

There total 74 articles about Aspidospermine 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: 83.0%

(+)-deacetylaspidospermine (2447-50-9) + acetic anhydride (108-24-7) → aspidospermine (466-49-9)

Guidance literature:

With pyridine; at 20 ℃; for 3h;

DOI:10.1021/acs.orglett.7b01292

Reference yield:

(+)-dehydrodeacetylaspidospermine (2912-26-7) → aspidospermine (466-49-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 35.4 mg / LiAlH₄ / tetrahydrofuran / 24 h / 20 °C

2: 33.3 mg / pyridine / 3 h / 20 °C

With pyridine; lithium aluminium tetrahydride; In tetrahydrofuran;

DOI:10.1021/ol034020s

Reference yield:

C35H36N2O5 → aspidospermine (88198-98-5) + aspidospermine (466-49-9)

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; 4-nitro-benzoic acid / toluene / 5 h / 23 °C

6.1: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / 23 - 70 °C / Reflux

7.1: palladium 10% on activated carbon; hydrogen / methanol; dichloromethane / 3.17 h / 23 °C

8.1: pyridine / 18 h / 23 °C

8.2: 2 h / Inert atmosphere

9.1: methanol; diethyl ether; toluene / 64 h

10.1: chiralcel AD / hexane; isopropyl alcohol

With pyridine; lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; ammonia; hydrogen; sodium tri-sec-butylborohydride; acetyl chloride; triphenylphosphine; trifluoroacetic anhydride; 4-nitro-benzoic acid; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; isopropyl alcohol; toluene;

DOI:10.1021/ol300599p

upstream raw materials:

(9Ξ)-1-acetyl-17-methoxy-aspidospermidine-9-oxide

(+)-deacetylaspidospermine

acetic anhydride

(+)-dehydrodeacetylaspidospermine

Downstream raw materials:

(+)-deacetylaspidospermine

aspidospermine

Refernces

• 1、 Yang, Lu,Huang, Siwen,Huang, Rongkang,Hou, Anbin,Zhang, Sen,Su, Hongwei,Ding, Xiaohong,Lin, Bin,Cheng, Maosheng,Liu, Yongxiang. "Total Syntheses of Aspidospermidine, N-Methylaspidospermidine, N-Acetylaspidospermidine, and Aspidospermine via a Tandem Cyclization of Tryptamine-Ynamide". . p. 6471 - 6476. Retrieved 2021/08/23.
• 2、 Lajiness, James P.,Jiang, Wanlong,Boger, Dale L.. "Divergent total syntheses of (-)-aspidospermine and (+)-spegazzinine". . p. 2078 - 2081. Retrieved 2012/06/18.