92870-51-4

Basic information

• Product Name: methyl 4-{[2-(1H-indol-3-yl)ethyl]amino}-4-oxobutanoate
• CAS NO: 92870-51-4
• Molecular Formula: C₁₅H₁₈N₂O₃
• Molecular Weight: 274.315
• Mol File: 92870-51-4.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 546.1°C at 760 mmHg
• Flash Point: 284.1°C
• Density: 1.21g/cm³
• Vapor Pressure: 5.55E-12mmHg at 25°C
• Refractive Index: 1.591
• CAS DataBase Reference: methyl 4-{[2-(1H-indol-3-yl)ethyl]amino}-4-oxobutanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-{[2-(1H-indol-3-yl)ethyl]amino}-4-oxobutanoate(92870-51-4)
• EPA Substance Registry System: methyl 4-{[2-(1H-indol-3-yl)ethyl]amino}-4-oxobutanoate(92870-51-4)

Safety Data

• Hazardous Substances Data: 92870-51-4(Hazardous Substances Data)

Upstream product

• 61-54-1 tryptamine 
• 1501-26-4 methyl 4-(chlorocarbonyl)butyrate 
• 108-30-5 succinic acid anhydride 
• 67-56-1 methanol 
• 3878-55-5 methyl hydrogen succinate 
• 92256-33-2 N-(2-indol-3-yl-ethyl)-succinamic acid 
• 1490-25-1 succinic acid monomethylester chloride 
• 186581-53-3 diazomethane 

Downstream Products

• 60755-87-5 canthin-6-one-3-N-oxide 
• 479-43-6 canthin-6-one 
• 91147-07-8 3-(9H-Pyrido<3,4-b>indol-1-yl)propansaeure-methylester 
• 32283-51-5 1,2,5,6,11,11b-hexahydro-indolizino[8,7-b]indol-3-one 

Relevant articles and documents

Cyclopropenones in the synthesis of indolizidine, pyrrolo[2,1-a]isoquinoline and indolizino[8,7-b]indole alkaloids

An attempted synthesis of the indolizidine natural product castanospermine resulted in the successful addition of cyclopropenone to a sugar-derived poly-hydroxylated cyclic imine to give an indolizidinone product, but with the installation of an extra hydroxy group at the castanospermine 8a-bridgehead position. This was also observed in our previous approach to the australine and hyacinthacine pyrrolizidine natural products. The same oxidative phenomenon occurred during the synthesis of pyrrolo[1,2-a]isoquinolines from the reaction of aldimine dihydroisoquinolines with cyclopropenones, whereas ketimine based dihydroisoquinolines gave pyrrolo[1,2-a]isoquinolines without bridgehead oxidation. These results may have some significance for the origins of the bridgehead hydroxy natural products jenamidine B1/B2, clazamycin A/B and legonmycin A/B. The precursor cyclic aldimine for the synthesis of the indolizino[8,7-b]indoles gave dimeric indolizino[8,7-b]indoles, whereas the corresponding cyclic ketimines behaved as expected and gave the indolizino[8,7-b]indole core after reaction with cyclopropenones.

USE OF CANTHIN-6-ONE AND ITS ANALOGS IN THE TREATMENT OF MYCOBACTERIA-LINKED PATHOLOGIES ( amended

The present invention relates to the use, for the preparation of a medicament intended for the treatment or the prevention of pathologies linked to, or caused by mycobacteria, of at least one of the compounds of the following formula (I): in which B represents in particular a nitrogen atom, and R1, R2, R3, R4, R5, R6, R7 and R8 represent in particular a hydrogen atom.

Novel supramolecular palladium catalyst for the asymmetric reduction of imines in aqueous media

A novel approach to the asymmetric reduction of dihydro-β-carboline derivatives to the corresponding tetrahydro-β-carbolines is described based on the supramolecular lyophilized complex formed from β-cyclodextrin/ imines as an enzyme mimetic and palladium hydride as the reducing agent. The methodology allowed us to develop a short and efficient preparation of (R)-harmicine and (R)-deplancheine alkaloids in high overall yields and ee of 89 and 90%, respectively.