Aspidospermidine, (+)-

Base Information

• Chemical Name: Aspidospermidine, (+)-
• CAS No.: 2912-09-6
• Molecular Formula: C₁₉H₂₆N₂
• Molecular Weight: 282.429
• UNII: 38EV97NHY2
• DSSTox Substance ID: DTXSID301045567
• Nikkaji Number: J39.325H
• Wikipedia: Aspidospermidine
• Wikidata: Q104402848
• Metabolomics Workbench ID: 52225
• Mol file: 2912-09-6.mol

Synonyms:aspidospermidine

Chemical Property of Aspidospermidine, (+)-

Chemical Property:

• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 282.209598838
• Heavy Atom Count: 21
• Complexity: 435

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC12CCCN3C1C4(CC3)C(CC2)NC5=CC=CC=C45
• Isomeric SMILES: CC[C@]12CCCN3[C@H]1[C@@]4(CC3)[C@@H](CC2)NC5=CC=CC=C45

Technology Process of Aspidospermidine, (+)-

There total 122 articles about Aspidospermidine, (+)- 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: 98.0%

C26H26N2 → (+)-aspidospermidine (7013-58-3,7689-02-3,32975-45-4,52152-79-1,2912-09-6)

Guidance literature:

With hydrogen; palladium(II) hydroxide; In methanol; ethyl acetate; at 23 ℃; under 10343.2 Torr;

DOI:10.1038/nature10232

Reference yield: 90.0%

5-oxo-aspidospermidine (477904-34-0) → (+)-aspidospermidine (7013-58-3,7689-02-3,32975-45-4,52152-79-1,2912-09-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 3h; Heating;

DOI:10.1021/ja026357f

Reference yield: 83.0%

(+)-1,2-didehydroaspidospermidine (19751-76-9,56245-51-3,65377-84-6) → (+)-aspidospermidine (7013-58-3,7689-02-3,32975-45-4,52152-79-1,2912-09-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 ℃; for 12h; Reflux;

DOI:10.1021/acs.orglett.7b01292

upstream raw materials:

(+)-2,3-Didehydro-1-<(4-methoxyphenyl)sulfonyl>aspidospermidin-10-one

(3¹S,6aR,9aR)-6a-ethyloctahydro-1H-pyrrolo[3,2,1-ij]quinolin-9(2H)-one

phenylhydrazine

5-oxo-aspidospermidine

Downstream raw materials:

(+)-vincadifformine

(+)-1,2-didehydroaspidospermidine

(-)-N-acetylaspidospermidine

(-)-demethoxypalosine

Refernces

• 1、 Antropow, Alyssa H.,Garcia, Nicholas R.,White, Kolby L.,Movassaghi, Mohammad. "Enantioselective Synthesis of (-)-Vallesine: Late-Stage C17-Oxidation via Complex Indole Boronation". supporting information. p. 3647 - 3650. Retrieved 2018/06/26.
• 2、 Shemet, Andrej,Carreira, Erick M.. "Total Synthesis of (-)-Rhazinilam and Formal Synthesis of (+)-Eburenine and (+)-Aspidospermidine: Asymmetric Cu-Catalyzed Propargylic Substitution". supporting information. p. 5529 - 5532. Retrieved 2017/10/25.