80408-57-7

Basic information

• Product Name: 1,3-BIS(1-METHYL-2-PYURROLIDINYL)-2-PROPENOL
• Synonyms: 1,3-BIS(1-METHYL-2-PYURROLIDINYL)-2-PROPENOL;1,3-Bis(1-methyl-2-pyrrolidinyl)-2-propenol;Dihydrocuscohygrine 1-Methyl-((1-methyl-2-pyrrolidinyl)methyl)-2-pyrrolidineethanol
• CAS NO: 80408-57-7
• Molecular Formula: MW:
• Molecular Weight: 0
• Mol File: 80408-57-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3-BIS(1-METHYL-2-PYURROLIDINYL)-2-PROPENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-BIS(1-METHYL-2-PYURROLIDINYL)-2-PROPENOL(80408-57-7)
• EPA Substance Registry System: 1,3-BIS(1-METHYL-2-PYURROLIDINYL)-2-PROPENOL(80408-57-7)

Safety Data

• Hazardous Substances Data: 80408-57-7(Hazardous Substances Data)

Usage

Type of compound

Synthetic chemical compound

Potential applications

Pharmaceutical industry

Specific use

Cholinergic agonist

Target condition

Alzheimer's disease treatment

Mechanism of action

Potent inhibitor of acetylcholinesterase enzyme

Enzyme function

Breaks down acetylcholine neurotransmitter in the nervous system

Effect on neurotransmitter levels

Increases acetylcholine levels in the brain

Potential benefits

Improved cognitive function and memory in Alzheimer's patients

Other possible applications

Treatment of other neurological disorders and diseases

Upstream product

• 50-00-0 formaldehyd 
• 147-85-3 L-proline 
• 113304-84-0 N-benzyl-(S)-proline methyl ester 
• 53912-80-4 (S)-N-benzylprolinol 
• 176240-12-3 (2S)-1-benzylpirrolidine-2-carbaldehyde 
• 466645-81-8 N-allyl-N-[4-allylamino-6-(tert-butyl-dimethyl-silanyloxy)-cyclohept-2-enyl]-4-nitro-benzenesulfonamide 
• 466645-77-2 Acetic acid (1S,4S,6S)-4-[allyl-(4-nitro-benzenesulfonyl)-amino]-6-(tert-butyl-dimethyl-silanyloxy)-cyclohept-2-enyl ester 
• 466645-83-0 C₂₃H₄₄N₂O₅Si 
• 466645-82-9 Allyl-[(1S,4S)-4-(allyl-ethoxycarbonyl-amino)-6-(tert-butyl-dimethyl-silanyloxy)-cyclohept-2-enyl]-carbamic acid ethyl ester 
• 466645-79-4 N-allyl-N-[6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-cyclohept-2-enyl]-4-nitro-benzenesulfonamide 
• 466645-80-7 N-allyl-N-[6-(tert-butyl-dimethyl-silanyloxy)-4-chloro-cyclohept-2-enyl]-4-nitro-benzenesulfonamide 
• 134734-52-4 (1R,4S,6S)-4-acetoxy-6-[(tert-butyldimethylsilyl)oxy]-2-cyclohepten-1-ol 
• 466645-84-1 C₁₉H₄₀N₂OSi 
• 454-14-8 cuscohygrine 

Relevant articles and documents

Synthesis of acyclic ketones by catalytic, bidirectional homologation of formaldehyde with nonstabilized diazoalkanes. Application of a chiral diazomethyl(pyrrolidine) in total syntheses of erythroxylon alkaloids

This work offers a catalytic approach to convergent ketone assembly based upon formal and tandem C-H insertion of diazoalkanes in the presence of limiting amounts of monomeric formaldehyde, which is easily generated as a gas by thermolysis of the inexpensive and abundant paraformaldehyde (～30 USD/kg). The method forms di-, tri-, and even tetrasubstituted acetones with high efficiency, and it has streamlined a synthesis of (-)-dihydrocuscohygrine in which the absolute stereochemistry of a proline-based starting material is preserved. Assisted by the advent of new protocols for hydrazone oxidation, we also provide full details on handling non-carbonyl-stabilized diazo compounds.

Total synthesis of (+)-dihydrocuscohygrine and cuscohygrine

The first enantioselective synthesis of (+)-dihydrocuscohygrine 1 and cuscohygrine 2 is presented. 1 was obtained in nine steps and 30% overall yield with a ruthenium-catalyzed tandem ring rearrangement metathesis key step starting from enantiomerically pure cycloheptene-1,3,5-triol derivative 6. The unknown absolute configuration of natural dihydrocuscohygrine 1 could be determined as (S,S)-(-). Cuscohygrine 2 was obtained by Jones oxidation of 1 in quantitative yield but unfortunately with complete epimerization.