62209-18-1

Basic information

• Product Name: (±)-Donaxaridine
• Synonyms: (±)-Donaxaridine;Donaxaridine
• CAS NO: 62209-18-1
• Molecular Formula: C11H14N2O2
• Molecular Weight: 206.24
• Mol File: 62209-18-1.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (±)-Donaxaridine(CAS DataBase Reference)
• NIST Chemistry Reference: (±)-Donaxaridine(62209-18-1)
• EPA Substance Registry System: (±)-Donaxaridine(62209-18-1)

Safety Data

• Hazardous Substances Data: 62209-18-1(Hazardous Substances Data)

Usage

Occurrence

An alkaloid from the grass Arundo domax.

Upstream product

• 63637-70-7 methyl (2-(1H-indol-3-yl)ethyl)(methyl)carbamate 
• 61-49-4 [2-(1H-indol-3-yl)-ethyl]-methylamine 
• 1027024-06-1 Acetic acid 2-(3-bromo-2-oxo-2,3-dihydro-1H-indol-3-yl)-ethyl ester 
• 195132-42-4 Acetic acid 2-(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-ethyl ester 
• 195132-43-5 3-hydroxy-3-(2-hydroxyethyl)indolin-2-one 
• 91-56-5 indole-2,3-dione 
• 910035-64-2 ethyl (2Z)-(2-oxo-1,2-dihydro-3H-indol-3-ylidene)acetate 
• 3690-95-7 (+/-)-3-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one 
• 68104-18-7 3-(2-acetoxyethyl)-2-indolinone 
• 220598-39-0 3-allyl-3-hydroxy-1,3-dihydro-2H-indol-2-one 
• 74-89-5 methylamine 
• 195132-44-6 2-(3-hydroxy-2-oxoindolin-3-yl)ethyl 4-methylbenzenesulfonate 

Downstream Products

• 62209-19-2 2′,3′-dimethylspiro[indoline-3,6′-(1,3)oxazinan]-2-one 

Relevant articles and documents

Regioselective oxidation of indoles to 2-oxindoles

Facile regioselective oxidation of indoles to 2-oxindoles promoted by sulfuric acid adsorbed on silica gel is reported. The demonstrated practical site-selective heterogeneous oxidation reactions conveniently take place with a broad substrate scope and functional group tolerances. The present oxidation strategy is also employed to accomplish the total synthesis of natural products donaxaridine and donaxarine. On the basis of analytical and spectral data it is evidenced that donaxarine stays in equilibrium with its hydrated ring opened form. The structural features essential for this type of oxidation and plausible mechanism are discussed in brief.

Synthesis of 3-hydroxyindolin-2-one alkaloids, (±)-donaxaridine and (±)-convolutamydines A and E, through enolization-Claisen rearrangement of 2-allyloxyindolin-3-ones

Claisen rearrangement triggered by enolization of 2-allyloxyindolin-3-ones with DBU was performed in order to prepare 3-allyl-3-hydroxyindolin-2-ones. Total synthesis of 3-hydroxyindolin-2-one alkaloids, (±)-donaxaridine, as well as (±)-convolutamydines A