27300-29-4

Basic information

• Product Name: 3,11-Dihydro-3,3-dimethylpyrano[3,2-a]carbazole-5-carbaldehyde
• Synonyms: 3,11-Dihydro-3,3-dimethylpyrano[3,2-a]carbazole-5-carbaldehyde;Murrayacine;3,3-dimethyl-3,11-dihydropyrano[3,2-a]carbazole-5-carbaldehyde
• CAS NO: 27300-29-4
• Molecular Formula: C18H15 N O2
• Molecular Weight: 277.32
• Mol File: 27300-29-4.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,11-Dihydro-3,3-dimethylpyrano[3,2-a]carbazole-5-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3,11-Dihydro-3,3-dimethylpyrano[3,2-a]carbazole-5-carbaldehyde(27300-29-4)
• EPA Substance Registry System: 3,11-Dihydro-3,3-dimethylpyrano[3,2-a]carbazole-5-carbaldehyde(27300-29-4)

Safety Data

• Hazardous Substances Data: 27300-29-4(Hazardous Substances Data)

Usage

Description

3,11-Dihydro-3,3-dimethylpyrano[3,2-a]carbazole-5-carbaldehyde is a carbazole alkaloid found in Murraya koenigii Spreng. 3,11-Dihydro-3,3-dimethylpyrano[3,2-a]carbazole-5-carbaldehyde forms colorless crystals when dissolved in ethanol (EtOH). It exhibits an ultraviolet spectrum with three absorption maxima at 226, 284, and 301 mil. The structure of this compound has been recently revised, with the formyl group now positioned in the second benzene ring of the carbazole nucleus.

Uses

Used in Pharmaceutical Industry:
3,11-Dihydro-3,3-dimethylpyrano[3,2-a]carbazole-5-carbaldehyde is used as a pharmaceutical compound for its potential therapeutic applications. The compound's unique structure and properties make it a promising candidate for the development of new drugs, particularly in the areas of cancer treatment and other diseases.
Used in Chemical Research:
In the field of chemical research, 3,11-Dihydro-3,3-dimethylpyrano[3,2-a]carbazole-5-carbaldehyde serves as a valuable compound for studying the properties and reactivity of carbazole alkaloids. Its unique structure and absorption characteristics can provide insights into the behavior of similar compounds and contribute to the advancement of chemical knowledge.
Used in Material Science:
3,11-Dihydro-3,3-dimethylpyrano[3,2-a]carbazole-5-carbaldehyde may also find applications in material science, particularly in the development of new materials with specific optical, electronic, or structural properties. The compound's unique structure and absorption characteristics could be exploited to create novel materials with tailored properties for various applications.

References

Chakraborty, Das., Chern. Cornrnun., 967 (1966)Revised structure: Joshi, Kamat, Gawad., Tetrahedron, 26, 1475 (1970)

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Relevant articles and documents

Pd-Catalyzed Formal [3 + 3] Heteroannulation of Allylic gem-Diacetates: Synthesis of Chromene-Based Natural Products and Exploration of Photochromic Properties

Palladium-catalyzed allylic alkylation reactions of allylic gem-diacetates are rarely explored. This work unveils an unusual chemical reactivity pattern of allylic gem-diacetates and establishes them as new prototypes to synthesize complex benzo[f]chromene systems. Under the reaction conditions, the diacetates behave as 1,3-dicationic equivalents and undergo a [3 + 3] heteroannulation with 2-naphthols (and meta-substituted phenols) to produce novel polycyclic chromenes possessing spiro-, tri-, and tetrasubstituted carbon centers. The versatility of the method is demonstrated in the synthesis of several chromene-based bioactive natural products. Further, interesting photochromic properties of the new classes of benzo[f]chromenes are also discovered.

"on Water" Promoted Ullmann-Type C-N Bond-Forming Reactions: Application to Carbazole Alkaloids by Selective N-Arylation of Aminophenols

The Ullmann-type cross coupling of a variety of aromatic, aliphatic amines with aryl halides is reported using a CuI-based catalytic system in combination with an easily accessible prolinamide ligand in aqueous media. The method is mild and tolerant to air, moisture, and a wide range of functional groups, providing a novel way to access a variety of aminated products. Secondary amines like heteroaromatic amines and nucleobases have also been used, affording the corresponding coupling products in good to excellent yields. Moreover, this method has been employed for chemoselective C-N arylation of aminophenols and further utilized for the synthesis of carbazole natural products, avoiding the protection and deprotection steps.

Synthesis of Methylene-Bridged Biscarbazole Alkaloids by using an Ullmann-type Coupling: First Total Synthesis of Murrastifoline-C and Murrafoline-E

We describe the total synthesis of methylene-bridged biscarbazole alkaloids by using a late-stage Ullmann-type coupling of fully functionalised carbazole subunits. The carbazole derivatives were synthesised via a sequence of palladium(0)- and palladium(II