N-Acetylnorloline

Base Information

• Chemical Name: N-Acetylnorloline
• CAS No.: 38964-35-1
• Molecular Formula: C9H14N2O2
• Molecular Weight: 182.2197
• Metabolomics Workbench ID: 108705
• Wikidata: Q77497048
• Mol file: 38964-35-1.mol

Synonyms:N-Acetylnorloline;38964-35-1;N-[(1R,3S,7S,8R)-2-oxa-6-azatricyclo[4.2.1.03,7]nonan-8-yl]acetamide;Demethyl-N-acetylloline;Acetamide, N-(hexahydro-2,4-methano-4H-furo(3,2-b)pyrrol-3-yl)-, (2R-(2alpha,3alpha,3abeta,4alpha,6abeta))-

Chemical Property of N-Acetylnorloline

Chemical Property:

• Vapor Pressure: 5.77E-06mmHg at 25°C
• Boiling Point: 379.6°Cat760mmHg
• Flash Point: 183.4°C
• PSA: 41.57000
• Density: 1.28g/cm³
• LogP: -0.32480
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 182.105527694
• Heavy Atom Count: 13
• Complexity: 256

Purity/Quality:

99% ^*data from raw suppliers

N-Acetylnorloline ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)NC1C2CN3C1C(O2)CC3
• Isomeric SMILES: CC(=O)N[C@H]1[C@H]2CN3[C@@H]1[C@@H](O2)CC3

Technology Process of N-Acetylnorloline

There total 12 articles about N-Acetylnorloline 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:

C15H26N2O7S → N-acetylnorloline (38964-35-1)

Guidance literature:

C₁₅H₂₆N₂O₇S; With trifluoroacetic acid; In dichloromethane; for 2.16667h;

With potassium carbonate; In acetonitrile; at 20 ℃; for 10h;

DOI:10.1039/c5cc07480k

Reference yield:

tert-butyl (2R,3aR,6aS)-2-((benzyloxy)methyl)-3-oxotetrahydro-2H-furo[3,2-b]pyrrole-4(5H)-carboxylate → N-acetylnorloline (38964-35-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: ammonia; titanium(IV) isopropylate / methanol / 10 h / 20 °C

1.2: 2.5 h / -20 - 0 °C

2.1: triethylamine / dichloromethane / 10.17 h / 0 - 38 °C

3.1: palladium hydroxide, 20 wt% on carbon; hydrogen / methanol / 8 h / 20 °C

4.1: triethylamine / dichloromethane / 0.08 h

5.1: trifluoroacetic acid / dichloromethane / 2.17 h

5.2: 10 h / 20 °C

With titanium(IV) isopropylate; palladium hydroxide, 20 wt% on carbon; ammonia; hydrogen; triethylamine; trifluoroacetic acid; In methanol; dichloromethane;

DOI:10.1039/c5cc07480k

Reference yield:

C19H28N2O4 → N-acetylnorloline (38964-35-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / dichloromethane / 10.17 h / 0 - 38 °C

2.1: palladium hydroxide, 20 wt% on carbon; hydrogen / methanol / 8 h / 20 °C

3.1: triethylamine / dichloromethane / 0.08 h

4.1: trifluoroacetic acid / dichloromethane / 2.17 h

4.2: 10 h / 20 °C

With palladium hydroxide, 20 wt% on carbon; hydrogen; triethylamine; trifluoroacetic acid; In methanol; dichloromethane;

DOI:10.1039/c5cc07480k

upstream raw materials:

(1'S,2R,4''R)-2-[(2,2-dimethyl-[1,3]dioxolan-4-yl)hydroxymethyl]-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylic acid tert-butyl ester

tert-butyl (R)-2-((S)-((tert-butyldimethylsilyl)oxy)((R)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

Downstream raw materials:

Norlolin

Refernces