136816-12-1

Basic information

• Product Name: ((2aR,4S)-4-Amino-6-iodo-2a,3,4,5-tetrahydro-2H-benzo[cd]indol-1-yl)-phenyl-methanone
• Synonyms: ((2aR,4S)-4-Amino-6-iodo-2a,3,4,5-tetrahydro-2H-benzo[cd]indol-1-yl)-phenyl-methanone
• CAS NO: 136816-12-1
• Molecular Weight: 404.25
• Mol File: 136816-12-1.mol

Chemical Properties

• CAS DataBase Reference: ((2aR,4S)-4-Amino-6-iodo-2a,3,4,5-tetrahydro-2H-benzo[cd]indol-1-yl)-phenyl-methanone(CAS DataBase Reference)
• NIST Chemistry Reference: ((2aR,4S)-4-Amino-6-iodo-2a,3,4,5-tetrahydro-2H-benzo[cd]indol-1-yl)-phenyl-methanone(136816-12-1)
• EPA Substance Registry System: ((2aR,4S)-4-Amino-6-iodo-2a,3,4,5-tetrahydro-2H-benzo[cd]indol-1-yl)-phenyl-methanone(136816-12-1)

Safety Data

• Hazardous Substances Data: 136816-12-1(Hazardous Substances Data)

Upstream product

• 132619-29-5 (+)-1-Benzoyl-1,2,2a,3,4,5-hexahydrobenzindol-4-amine 
• 363-39-3 (S)-3-(1H-indol-3-yl)-2-(2,2,2-trifluoroacetamido)propanoic acid 
• 133148-95-5 (S)-3-((R)-1-Benzoyl-2,3-dihydro-1H-indol-3-yl)-2-(2,2,2-trifluoro-acetylamino)-propionic acid 
• 133148-98-8 N-((2aR,4S,5S)-1-Benzoyl-5-hydroxy-1,2,2a,3,4,5-hexahydro-benzo[cd]indol-4-yl)-2,2,2-trifluoro-acetamide 
• 133148-97-7 N-((2aR,4S)-1-Benzoyl-5-oxo-1,2,2a,3,4,5-hexahydro-benzo[cd]indol-4-yl)-2,2,2-trifluoro-acetamide 
• 132557-12-1 [(2aR,4R,5R)-4-Hydroxy-5-((S)-1-phenyl-ethylamino)-2a,3,4,5-tetrahydro-2H-benzo[cd]indol-1-yl]-phenyl-methanone 
• 132557-13-2 Phenyl-[(5aR,6aS,7aR)-7-((S)-1-phenyl-ethyl)-5,5a,6,6a,7,7a-hexahydro-4,7-diaza-cyclopropa[e]acenaphthylen-4-yl]-methanone 
• 133445-35-9 (S)-3-((R)-1-Benzoyl-2,3-dihydro-1H-indol-3-yl)-2-(2,2,2-trifluoro-acetylamino)-propionyl chloride 
• 133148-99-9 N-((2aR,4S)-1-Benzoyl-1,2,2a,3,4,5-hexahydro-benzo[cd]indol-4-yl)-2,2,2-trifluoro-acetamide 
• 39890-59-0 Phenyl-(5aS,6aS,7aR)-5a,6,6a,7a-tetrahydro-5H-7-oxa-4-aza-cyclopropa[e]acenaphthylen-4-yl-methanone 

Downstream Products

• 136791-10-1 (2aR,4S)-1-Benzoyl-4-dipropylamino-1,2,2a,3,4,5-hexahydro-benzo[cd]indole-6-carboxylic acid amide 
• 132557-16-5 (+)-(2aR,4S)-1-benzoyl-4-(dipropylamino)-1,2,2α,3,4,5-hexahydrobenz-[cd]-indole-6-carbonitrile 
• 115994-31-5 LY 228729 
• 133256-91-4 (+) (2aR,4S)-1-benzoyl-6-iodo-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole 

Relevant articles and documents

Application of palladium (O)-catalyzed processes to the synthesis of oxazole-containing partial ergot alkaloids

Syntheses of the potent 5-HT(1A) agonists 2 and 3 were accomplished in several steps from the 6-iodo partial ergoline alkaloid 8. Disparate tactics available for construction of differentially substituted oxazoles led to the development of new and general methodology critical to the efficient preparations of 2 and 3. A novel palladium(O)- and copper(I)-cocatalyzed cyanation reaction provided efficient access to the nitrile 10, a key intermediate in the synthesis of 2. A palladium(O)-catalyzed cross-coupling reaction of 16 with oxazole-2-lyzinc chloride formed the potent 5-HT(1A) agonist 3.

Synthetic studies toward the partial ergot alkaloid LY228729, a potent 5HT(1A) receptor agonist

Synthetic studies on LY228729 (3) afforded two innovative approaches for the construction of this class of partial ergoline 5HT(1a) receptor agonists. The first synthesis is based upon a diastereoselective epoxidation of racemic olefin 5, followed by ring