62209-19-2

Basic information

• Product Name: 2',3',4',5'-Tetrahydro-2',3'-dimethylspiro[3H-indole-3,6'-[6H-1,3]oxazin]-2(1H)-one
• Synonyms: 2',3',4',5'-Tetrahydro-2',3'-dimethylspiro[3H-indole-3,6'-[6H-1,3]oxazin]-2(1H)-one;Donaxarine
• CAS NO: 62209-19-2
• Molecular Formula: C13H16N2O2
• Molecular Weight: 232.28
• Mol File: 62209-19-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: 217 °C
• Boiling Point: 451.0±45.0 °C(Predicted)
• Appearance: /
• Density: 1.25±0.1 g/cm3(Predicted)
• PKA: 3.06±0.40(Predicted)
• CAS DataBase Reference: 2',3',4',5'-Tetrahydro-2',3'-dimethylspiro[3H-indole-3,6'-[6H-1,3]oxazin]-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3',4',5'-Tetrahydro-2',3'-dimethylspiro[3H-indole-3,6'-[6H-1,3]oxazin]-2(1H)-one(62209-19-2)
• EPA Substance Registry System: 2',3',4',5'-Tetrahydro-2',3'-dimethylspiro[3H-indole-3,6'-[6H-1,3]oxazin]-2(1H)-one(62209-19-2)

Safety Data

• Hazardous Substances Data: 62209-19-2(Hazardous Substances Data)

Usage

Occurrence

This alkaloid is isolated from the grass Arundo donax.

Upstream product

• 62209-18-1 (+/-)-donaxaridine 
• 75-07-0 acetaldehyde 
• 63637-70-7 methyl (2-(1H-indol-3-yl)ethyl)(methyl)carbamate 

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.