(+)-Cylindricine C

Base Information

• Chemical Name: (+)-Cylindricine C
• CAS No.: 634910-80-8
• Molecular Formula: C₁₉H₃₃NO₂
• Molecular Weight: 307.477
• DSSTox Substance ID: DTXSID10212894
• Metabolomics Workbench ID: 144071
• Nikkaji Number: J1.885.636K
• Wikidata: Q83088119

Synonyms:(+)-Cylindricine C;634910-80-8;DTXSID10212894

Chemical Property of (+)-Cylindricine C

Chemical Property:

• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 307.251129295
• Heavy Atom Count: 22
• Complexity: 397

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCCC1CC(=O)C2CCCCC23N1C(CC3)CO
• Isomeric SMILES: CCCCCC[C@@H]1CC(=O)[C@H]2CCCC[C@@]23N1[C@@H](CC3)CO

Technology Process of (+)-Cylindricine C

There total 1 articles about (+)-Cylindricine C 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:

(S)-Pyroglutaminol (17342-08-4) → (3S,5R,7aS,11aS)-5-hexyl-3-(hydroxymethyl)octahydro-1H-pyrrolo[2,1-j]quinolin-7(7aH)-one (634910-80-8)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

2.1: dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

4.1: oxalic acid; water / dichloromethane; methanol / 1 h / 0 - 20 °C / Inert atmosphere

5.1: potassium carbonate / dichloromethane; methanol / 20 °C

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 10 h / 0 - 20 °C / Inert atmosphere

7.1: lithium / diethyl ether / 1 h / -40 °C / Inert atmosphere

7.2: 0.33 h / -40 °C / Inert atmosphere

7.3: 1 h / -40 - 20 °C / Inert atmosphere

8.1: 3 h / 150 °C / Inert atmosphere

9.1: zinc; acetic acid / water / 5 h / 45 °C / Inert atmosphere

10.1: copper(l) chloride; dmap; 2-azatricyclo[3.3.1.1^3,7]decan-2-ol; [2,2]bipyridinyl / acetonitrile / 0.5 h / 20 °C / Inert atmosphere

11.1: TurboGrignard / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

11.2: 0.17 h / 0 °C / Inert atmosphere

12.1: copper(l) chloride; dmap; 2-azatricyclo[3.3.1.1^3,7]decan-2-ol; [2,2]bipyridinyl / acetonitrile / 4.5 h / 20 °C / Inert atmosphere

13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

14.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 1.5 h / 45 °C / Inert atmosphere

With 1H-imidazole; dmap; [2,2]bipyridinyl; TurboGrignard; 2-azatricyclo[3.3.1.1^3,7]decan-2-ol; tetrabutyl ammonium fluoride; water; oxalic acid; lithium; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; copper(l) chloride; zinc; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/anie.201901049

upstream raw materials:

(S)-Pyroglutaminol

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