2-Propenal,2-methyl-3-[(4R,5R)-1,3,4,5-tetrahydro-4-(methylamino)benz[cd]indol-5-yl]-,(2E)-

Base Information

• Chemical Name: 2-Propenal,2-methyl-3-[(4R,5R)-1,3,4,5-tetrahydro-4-(methylamino)benz[cd]indol-5-yl]-,(2E)-
• CAS No.: 25800-42-4
• Molecular Formula: C16H18 N2 O
• Molecular Weight: 254.332
• Mol file: 25800-42-4.mol

Synonyms:2-Propenal,2-methyl-3-[1,3,4,5-tetrahydro-4-(methylamino)benz[cd]indol-5-yl]-, [4R-[4a,5b(E)]]-; 6,7-Secoergoline-8-carboxaldehyde,8,9-didehydro-6-methyl- (8CI); Benz[cd]indole, 2-propenal deriv.; ChanoclavineI aldehyde

Chemical Property of 2-Propenal,2-methyl-3-[(4R,5R)-1,3,4,5-tetrahydro-4-(methylamino)benz[cd]indol-5-yl]-,(2E)-

Chemical Property:

• Boiling Point: 474.0±45.0 °C(Predicted)
• PSA: 44.89000
• Density: 1.18±0.1 g/cm3(Predicted)
• LogP: 2.93170

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Propenal,2-methyl-3-[(4R,5R)-1,3,4,5-tetrahydro-4-(methylamino)benz[cd]indol-5-yl]-,(2E)-

There total 2 articles about 2-Propenal,2-methyl-3-[(4R,5R)-1,3,4,5-tetrahydro-4-(methylamino)benz[cd]indol-5-yl]-,(2E)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C17H20N2O2 → (E)-2-methyl-3-((4R,5R)-4-(methylamino)-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl)acrylaldehyde (25800-42-4) + chanoclavine (2390-99-0,11012-16-1)

Guidance literature:

With N-His₆-EasC catalase from E_. coli strain BL₂₁; dihydrogen peroxide; NADPH; In aq. buffer; at 28 ℃; for 4h; pH=7.5; Reagent/catalyst; Enzymatic reaction;

DOI:10.1021/jacs.9b10217

Reference yield:

C17H22N2O2 → (E)-2-methyl-3-((4R,5R)-4-(methylamino)-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl)acrylaldehyde (25800-42-4) + chanoclavine (2390-99-0,11012-16-1)

Guidance literature:

Multi-step reaction with 2 steps

1: FAD binding oxidoreductase from Aspergillus fumigatus / 48 h / Microbiological reaction; Enzymatic reaction

2: NADPH; dihydrogen peroxide; N-His₆-EasC catalase from E_. coli strain BL₂₁ / aq. buffer / 4 h / 28 °C / pH 7.5 / Enzymatic reaction

With FAD binding oxidoreductase from Aspergillus fumigatus; N-His₆-EasC catalase from E_. coli strain BL₂₁; dihydrogen peroxide; NADPH; In aq. buffer;

DOI:10.1021/jacs.9b10217

Reference yield: 35.0%

(E)-2-methyl-3-((4R,5R)-4-(methylamino)-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl)acrylaldehyde (25800-42-4) → Pyroclavin (478-89-7) + festuclavine (569-26-6)

Guidance literature:

(E)-2-methyl-3-((4R,5R)-4-(methylamino)-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl)acrylaldehyde; With palladium 10% on activated carbon; hydrogen; In methanol; at 25 ℃; for 1h; under 760.051 Torr;

With methanol; sodium tetrahydroborate; at 0 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b03683

Downstream raw materials:

agroclavine

festuclavine

(+)-cycloclavine

Pyroclavin