28200-63-7

Basic information

• Product Name: 3,11-Dihydro-3,3,5-trimethylpyrano[3,2-a]carbazol-8-ol
• Synonyms: 3,11-Dihydro-3,3,5-trimethylpyrano[3,2-a]carbazol-8-ol;Kenine;Koenine
• CAS NO: 28200-63-7
• Molecular Formula: C18H17 N O2
• Molecular Weight: 0
• Mol File: 28200-63-7.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,11-Dihydro-3,3,5-trimethylpyrano[3,2-a]carbazol-8-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3,11-Dihydro-3,3,5-trimethylpyrano[3,2-a]carbazol-8-ol(28200-63-7)
• EPA Substance Registry System: 3,11-Dihydro-3,3,5-trimethylpyrano[3,2-a]carbazol-8-ol(28200-63-7)

Safety Data

• Hazardous Substances Data: 28200-63-7(Hazardous Substances Data)

Usage

Description

A further constituent of the leaves of Murraya koenigii Spreng. this alkaloid forms colourless crystals from EtOH. The base contains one hydroxyl group and three methyl groups, again with two of the latter being gem dimethyls.

References

Kureel et at., Chem. & Ind., 1262 (I970) Narasimhan et at., Ind. J. Chem., 8,473 (1970)

Upstream product

• 106-41-2 4-bromo-phenol 
• 127481-94-1 1-bromo-4-[[(1,1-dimethylethyl)-diphenylsilyl]-oxy]-benzene 

Downstream Products

• 21087-98-9 3,11-dihydro-8-methoxy-3,3,5-trimethylpyrano (3,2-a)carbazole 

Relevant articles and documents

Synthesis of the Pyrano[3,2- a ]carbazole Alkaloids Koenine, Koenimbine, Koenigine, Koenigicine, and Structural Reassignment of Mukonicine

Using the palladium(II)-catalyzed oxidative cyclization of a diarylamine and the annulation of a dimethylpyran ring by Lewis acid promoted reaction with prenal as key steps, the total syntheses of the 6-oxygenated pyrano[3,2-a]carbazole alkaloids koenine and koenimbine, and of the 6,7-dioxygenated pyrano[3,2-a]carbazole alkaloids koenigine and koenigicine (koenimbidine, koenidine) were achieved. Moreover, these studies led to an improved synthetic route to the 2,6-dioxygenated carbazole alkaloid glycozolidol. Mukonicine, originally published as 6,8-dimethoxypyrano[3,2-a]carbazole, was found to be identical with koenigicine.