478-89-7

Basic information

• Product Name: (8alpha)-6,8-dimethylergoline
• Synonyms: 6,8alpha-Dimethylergoline; Ergoline, 6,8alpha-dimethyl-; ergoline, 6,8-dimethyl-, (8alpha)-
• CAS NO: 478-89-7
• Molecular Formula: C₁₆H₂₀N₂
• Molecular Weight: 240.3434
• Mol File: 478-89-7.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 407.5°C at 760 mmHg
• Flash Point: 200.2°C
• Density: 1.123g/cm³
• Vapor Pressure: 7.53E-07mmHg at 25°C
• Refractive Index: 1.624
• CAS DataBase Reference: (8alpha)-6,8-dimethylergoline(CAS DataBase Reference)
• NIST Chemistry Reference: (8alpha)-6,8-dimethylergoline(478-89-7)
• EPA Substance Registry System: (8alpha)-6,8-dimethylergoline(478-89-7)

Safety Data

• Hazardous Substances Data: 478-89-7(Hazardous Substances Data)

Upstream product

• 74607-01-5 4-benzoyl-5,5a,6,8,9,10-hexahydro-9-methylindolo<4,3-fg>quinolin-8(4H)-one 
• 74607-02-6 1-benzoyl-4-methylamino-1,2,2a,3-tetrahydrobenzindole 
• 51867-06-2 1-benzoyl-1,2,2a,3-tetrahydrobenzindol-4-(5H)-one 
• 114249-82-0 7,9-Dimethyl-4,5,5a,6,6a,7,8,9,10,10a-decahydro-indolo[4,3-fg]quinoline 
• 51867-16-4 (5R^*,8R^*,10S^*)-6,8-dimethylergolin-7-one 
• 61361-27-1 (5β,10β)-2,3-dihydro-6,8-dimethylergolin-7-one 
• 51867-16-4 (5R^*,8S^*,10S^*)-6,8-dimethylergolin-7-one 
• 82617-49-0 2-bromo-1-bromomethyl-3-nitrobenzene 
• 25800-42-4 (E)-2-methyl-3-((4R,5R)-4-(methylamino)-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl)acrylaldehyde 

Relevant articles and documents

Biomimetic Total Syntheses of Ergot Alkaloids via Decarboxylative Giese Coupling

Biomimetic total syntheses of Festuclavine and Pyroclavine were achieved by a sequential radical coupling. The key steps include intramolecular decarboxylative Giese reaction to form the central C ring and 4-nitrobenzenesulfonyl (Ns)-directed indole C4-H olefination to introduce the indole C4 component. In addition, D-ring formation was completed by decarboxylative alkenylation and intramolecular SN2 reaction.

Biomimetic Total Syntheses of Clavine Alkaloids

Biomimetic total syntheses of either enantiomers of a number of ergot alkaloids, chanoclavine I (1b), chanoclavine I aldehyde (1c), pyroclavine (1e), festuclavine (1f), pibocin A (1g), 9-deacetoxyfumigaclavine C (1h), and fumigaclavine G (1i), have been achieved from seco-agroclavine (1a). The advanced intermediate for seco-agroclavine (1a) was synthesized via a key thiourea-catalyzed intramolecular nitronate addition onto α,β-unsaturated ester.

Total Syntheses of Pyroclavine, Festuclavine, Lysergol, and Isolysergol via a Catalytic Asymmetric Nitro-Michael Reaction

A catalytic enantioselective construction of vicinal stereocenters is reported. The reaction takes advantage of thiourea-catalyzed intramolecular nitronate addition onto α,β-unsaturated ester to afford exceptional levels of enantioselectivity (up to 97 % ee) with moderate diastereoselectivity (up to 4:1). Using this method, a cross-conjugated ester was synthesized in few steps, from which a 6-endo-trig cyclisation led to the formation of all required functionalities for total syntheses of ergot alkaloids. The strategy not only offers first total syntheses of ergot alkaloids, festuclavine (1 c), and pyroclavine (1 e), and but also an efficient and general approach to other congeners such as, lysergol (1 b), and isolysergol (1 d).