Murrayacine

Base Information

• Chemical Name: Murrayacine
• CAS No.: 27300-29-4
• Molecular Formula: C₁₈H₁₅NO₂
• Molecular Weight: 277.323
• UNII: NND4AMH54D
• DSSTox Substance ID: DTXSID701318174
• Nikkaji Number: J17.269C
• Wikidata: Q105269633
• Metabolomics Workbench ID: 46365
• Mol file: 27300-29-4.mol

Synonyms:Murrayacine;27300-29-4;3,3-dimethyl-11H-pyrano[3,2-a]carbazole-5-carbaldehyde;DTXSID701318174;3,3-DIMETHYL-3H,11H-PYRANO[3,2-A]CARBAZOLE-5-CARBALDEHYDE;3,11-Dihydro-3,3-dimethylpyrano[3,2-a]carbazole-5-carboxaldehyde, 9CI

Chemical Property of Murrayacine

Chemical Property:

• Melting Point: 244-5°C
• PSA: 42.09000
• LogP: 4.31780
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 277.110278721
• Heavy Atom Count: 21
• Complexity: 458

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C=CC2=C(O1)C(=CC3=C2NC4=CC=CC=C43)C=O)C
• Description: A carbazole alkaloid occurring in Murraya koenigii Spreng., this base forms colourless crystals from EtOH. It gives an ultraviolet spectrum showing three absorption maxima at 226, 284 and 301 mil. The structure has recently been revised, placing the formyl group in the second benzene ring of the carbazole nucleus.

Technology Process of Murrayacine

There total 49 articles about Murrayacine 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: 96.0%

girinimbine (23095-44-5) → 3',3'-dimethylpyrano[3,2-a]carbazole-3-carbaldehyde (27300-29-4)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; water; at 20 ℃; for 1.5h;

DOI:10.1039/c0ob01088j

Reference yield: 80.0%

3,3-dimethyl-3,11-dihydropyrano[3,2-a]carbazole-5-carbonitrile → 2-hydroxy-1-(3-methylbut-2-en-1-yl)-9H-carbazole-3-carbaldehyde (17750-35-5) + 3',3'-dimethylpyrano[3,2-a]carbazole-3-carbaldehyde (27300-29-4)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 3.5h;

DOI:10.1002/chem.201403645

Reference yield:

2-methoxy-4-nitrobenzonitrile (101084-96-2) → 2-hydroxy-1-(3-methylbut-2-en-1-yl)-9H-carbazole-3-carbaldehyde (17750-35-5) + 3',3'-dimethylpyrano[3,2-a]carbazole-3-carbaldehyde (27300-29-4)

Guidance literature:

Multi-step reaction with 7 steps

1: palladium 10% on activated carbon; hydrogen / methanol; dichloromethane / 23.5 h / 20 °C / 3750.38 - 4500.45 Torr

2: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; caesium carbonate / toluene / 29 h / 100 °C

3: palladium diacetate; copper diacetate; potassium carbonate; Trimethylacetic acid / 15.5 h / 100 - 120 °C

4: pyridine hydrochloride / 0.75 h / 155 °C / Microwave irradiation

5: copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 25.5 h / 20 °C

6: toluene / 25 h / Reflux

7: diisobutylaluminium hydride / dichloromethane; toluene / 3.5 h / -78 - -30 °C

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; copper(l) iodide; palladium 10% on activated carbon; hydrogen; copper diacetate; palladium diacetate; pyridine hydrochloride; diisobutylaluminium hydride; potassium carbonate; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; Trimethylacetic acid; In methanol; dichloromethane; toluene; acetonitrile; 2: |Buchwald-Hartwig Coupling;

DOI:10.1002/chem.201403645

upstream raw materials:

murrastinine-B

girinimbine

2-methyl-5-nitrophenol

5-amino-2,2,8-trimethylchromene

Refernces

• 1、 Mandal, Tirtha,Chakraborti, Gargi,Karmakar, Shilpi,Dash, Jyotirmayee. "Divergent and Orthogonal Approach to Carbazoles and Pyridoindoles from Oxindoles via Indole Intermediates". supporting information. p. 4759 - 4763. Retrieved 2018/08/24.
• 2、 Zang, Yingda,Song, Xiuyun,Li, Chuangjun,Ma, Jie,Chu, Shifeng,Liu, Dandan,Ren, Qian,Li, Yan,Chen, Naihong,Zhang, Dongming. "Pyrano[3,2-a]carbazole alkaloids as effective agents against ischemic stroke in vitro and in vivo". . p. 438 - 448. Retrieved 2017/12/07.