51743-69-2

Basic information

• Product Name: (E)-3-((4R,5R)-4-Amino-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl)-2-methyl-prop-2-en-1-ol
• CAS NO: 51743-69-2
• Molecular Weight: 242.321
• Mol File: 51743-69-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (E)-3-((4R,5R)-4-Amino-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl)-2-methyl-prop-2-en-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3-((4R,5R)-4-Amino-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl)-2-methyl-prop-2-en-1-ol(51743-69-2)
• EPA Substance Registry System: (E)-3-((4R,5R)-4-Amino-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl)-2-methyl-prop-2-en-1-ol(51743-69-2)

Safety Data

• Hazardous Substances Data: 51743-69-2(Hazardous Substances Data)

Upstream product

• 79133-62-3 4,5-trans-5-(2-methyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenz-indole 
• 106488-71-5 (E)-4,5-trans-5-(2-hydroxymethyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenzindole 
• 106488-71-5 (Z)-2-Methyl-3-((4S,5S)-4-nitro-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl)-prop-2-en-1-ol 
• 79133-62-3 (+)-4,5-cis-5-(2-methyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenzindole 
• 106488-71-5 E-4,5-cis-5-(2-hydroxymethyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenzindole 

Downstream Products

• 1150-43-2 (+/-)-chanoclavine I 
• 1150-43-2 (+/-)-isochanoclavine I 
• 548-42-5 (+/-)-Agroclavine 
• 1150-43-2 (+/-)-chanoclavine-II 
• 1150-43-2 (+)-chanoclavine-I 
• 2390-99-0 chanoclavine 

Relevant articles and documents

Synthetic studies directed toward ergot alkaloids, (±)-6,7-secoagroclavine, (±)-chanoclavine-1, (±)-chanoclavine-II, and (±)-agroclavine-I, by an efficient and common synthetic route

Novel three synthetic routes to (±)-6,7-secoagroclavine were developed from either methyl 3-(3-formylindol-4-yl)acrylate, indole-4-carbaldehyde, or 4-iodoindole-3-carbaldehyde. The total syntheses of (±)-chanoclavine-I, (±)-chanoclavine-II, and (±)-agroclavine-I were accomplished as well from the synthetic intermediates involved in the synthesis of (±)-6,7-secoagroclavine, culminating in establishing an efficient and common synthetic method for ergot alkaloids.

SHORT-STEP SYNTHESIS OF THE ERGOT ALKALOIDS, (+/-)-NORCHANOCLAVINE-I, (+/-)-CHANOCLAVINE-I, (+/-)-ISOCHANOCLAVINE-I, and (+/-)-AGROCLAVINE

The simple total synthesis of the ergot alkaloids, (+/-)-norchanoclavine-I, (+/-)-chanoclavine-I, (+/-)-isochanoclavine-I, and (+/-)-agroclavine was achieved by a practical and common synthesis method.A new regio-selective oxidation of the Z-methyl group of the isoprenyl system with selenium dioxide is described.Keywords - (+/-)-norchanoclavine-I; (+/-)-norisochanoclavine-I; (+/-)-chanoclavine-I; (+/-)-isochanoclavine-I; (+/-)-agroclavine; ergot alkaloid; total synthesis; common synthesis method; new oxidation