3,11-Dihydro-10-methoxy-3,3,5-trimethylpyrano[3,2-a]carbazole

Base Information

• Chemical Name: 3,11-Dihydro-10-methoxy-3,3,5-trimethylpyrano[3,2-a]carbazole
• CAS No.: 66003-49-4
• Molecular Formula: C₁₉H₁₉NO₂
• Molecular Weight: 293.365
• Mol file: 66003-49-4.mol

Synonyms:mupamine;Mupamin;10-methoxy-3,3,5-trimethyl-3,11-dihydro-pyrano[3,2-a]carbazole;10-Methoxy-3,3,5-trimethyl-3,11-dihydro-4-oxa-11-aza-benzo[a]fluorene;

Chemical Property of 3,11-Dihydro-10-methoxy-3,3,5-trimethylpyrano[3,2-a]carbazole

Chemical Property:

• PSA: 34.25000
• LogP: 4.82230

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3,11-Dihydro-10-methoxy-3,3,5-trimethylpyrano[3,2-a]carbazole

There total 14 articles about 3,11-Dihydro-10-methoxy-3,3,5-trimethylpyrano[3,2-a]carbazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

3,3-dimethyl acrylaldehyde (107-86-8) + 2-Hydroxy-8-methoxy-3-methyl-9H-carbazole (74059-97-5) → mupamine (66003-49-4)

Guidance literature:

With propionic acid; phenylboronic acid; In toluene; for 48h; Reagent/catalyst; Reflux;

DOI:10.1002/chem.201403143

Reference yield: 60.0%

dimethylacetal of 3-methyl-3-hydroxybutyraldehyde (31525-67-4) + 2-Hydroxy-8-methoxy-3-methyl-9H-carbazole (74059-97-5) → mupamine (66003-49-4)

Guidance literature:

Reference yield: 39.0%

3-chloro-3-methylbut-1-yne (1111-97-3) + 2-Hydroxy-8-methoxy-3-methyl-9H-carbazole (74059-97-5) → mupamine (66003-49-4)

Guidance literature:

With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 100 - 105 ℃; for 20h;

upstream raw materials:

3-chloro-3-methylbut-1-yne

2-Hydroxy-8-methoxy-3-methyl-9H-carbazole

dimethylacetal of 3-methyl-3-hydroxybutyraldehyde

cycloheptazoline

Refernces

• 1、 Julich-Gruner, Konstanze K.,Kataeva, Olga,Schmidt, Arndt W.,Knoelker, Hans-Joachim. "Total synthesis of 7- and 8-oxygenated pyrano[3,2-a]carbazole and pyrano[2,3-a]carbazole alkaloids via boronic acid-catalyzed annulation of the pyran ring". . p. 8536 - 8540. Retrieved 2014/07/21.
• 2、 Mester, Iuliu,Choudhury, Manash Kumar,Reisch, Johannes. "Constituents of Clausena anisata (Willd.) Oliv. (Rutaceae), IV- Synthesis of Mupamine". . p. 241 - 245. Retrieved 2007/10/02.