38964-35-1

Basic information

• Product Name: N-Acetyl-N-demethylloline
• Synonyms: (2R,3aβ,6aβ)-Hexahydro-N-acetyl-2α,4α-methano-4H-furo[3,2-b]pyrrol-3α-amine;(2R,3aβ,6aβ)-N-Acetylhexahydro-2,4α-methano-4H-furo[3,2-b]pyrrole-3α-amine;N-Acetyl-N-demethylloline;N-Acetylnorloline
• CAS NO: 38964-35-1
• Molecular Formula: C9H14N2O2
• Molecular Weight: 182.2197
• Mol File: 38964-35-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 379.6°Cat760mmHg
• Flash Point: 183.4°C
• Appearance: /
• Density: 1.28g/cm³
• Vapor Pressure: 5.77E-06mmHg at 25°C
• Refractive Index: 1.577
• CAS DataBase Reference: N-Acetyl-N-demethylloline(CAS DataBase Reference)
• NIST Chemistry Reference: N-Acetyl-N-demethylloline(38964-35-1)
• EPA Substance Registry System: N-Acetyl-N-demethylloline(38964-35-1)

Safety Data

• Hazardous Substances Data: 38964-35-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H14N2O2/c1-5(12)10-8-7-4-11-3-2-6(13-7)9(8)11/h6-9H,2-4H2,1H3,(H,10,12)/t6-,7?,8+,9+/m0/s1

Upstream product

• 141293-15-4 (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 
• 157720-16-6 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 Products

• 4839-19-4 Norlolin 

Relevant articles and documents

The asymmetric total synthesis of (+)-N-acetyl norloline

The asymmetric total synthesis of (+)-N-acetyl norloline, the putative biogenic precursor of all known loline alkaloids, has been achieved in 12 steps from commercially available (R)-glyceraldehyde acetonide. The synthesis relies on the Rassu/Casiraghi's vinylogous aldol reaction, an intramolecular oxa-heteroconjugate addition and a reductive amination to establish the four contiguous stereogenic centers and construct the strained oxygen-bridge under mild conditions.