Muramine

Base Information

• Chemical Name: Muramine
• CAS No.: 2292-20-8
• Molecular Formula: C₂₂H₂₇NO₅
• Molecular Weight: 385.46
• Hs Code.: 2933990090
• NSC Number: 148827
• UNII: EL76JUL1BM
• DSSTox Substance ID: DTXSID00177463
• Nikkaji Number: J14.179H
• Wikidata: Q83047791
• Metabolomics Workbench ID: 125884
• ChEMBL ID: CHEMBL1971249
• Mol file: 2292-20-8.mol

Synonyms:Muramine;Cryptopalmatine;2292-20-8;EL76JUL1BM;UNII-EL76JUL1BM;NSC 148827;NSC148827;NSC-148827;3,4,10,11-Tetramethoxy-6-methyl-5,7,8,14-tetrahydrodibenzo[c,g]azecin-13(6H)-one;5,7,8,14-Tetrahydro-3,4,10,11-tetramethoxy-6-methyldibenz[c,g]azecin-13(6H)-one;Dibenz[c,g]azecin-13(6H)-one, 5,7,8,14-tetrahydro-3,4,10,11-tetramethoxy-6-methyl-;3,4,10,11-Tetramethoxy-6-methyl-5,7,8,14-tetrahydrodibenzo(c,g)azecin-13(6H)-one;5,7,8,14-TETRAHYDRO-3,4,10,11-TETRAMETHOXY-6-METHYLDIBENZ(C,G)AZECIN-13(6H)-ONE;DIBENZ(C,G)AZECIN-13(6H)-ONE, 5,7,8,14-TETRAHYDRO-3,4,10,11-TETRAMETHOXY-6-METHYL-;SCHEMBL3271155;CHEMBL1971249;DTXSID00177463;CHEBI:194523;AKOS040735271;3,4,10,11-tetramethoxy-6-methyl-5,7,8,14-tetrahydrobenzo[e][2]benzazecin-13-one;NCI60_001022;Dibenz[c, 5,7,8,14-tetrahydro-3,4,10,11-tetramethoxy-6-methyl-;{Dibenz[c,g]azecin-13(6H)-one,} 5,7,8, 14-tetrahydro-3,4,10,11-tetramethoxy-6-methyl-;3,4,10,11-Tetramethoxy-6-methyl-5,7,8,14-tetrahydrodibenzo[c,g]azecin-13(6H)-one #

Chemical Property of Muramine

Chemical Property:

• Vapor Pressure: 2.2E-12mmHg at 25°C
• Melting Point: 148-150 °C
• Boiling Point: 555.6°Cat760mmHg
• PKA: 7.86±0.20(Predicted)
• Flash Point: 289.8°C
• PSA: 57.23000
• Density: 1.131g/cm³
• LogP: 3.07220
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 385.18892296
• Heavy Atom Count: 28
• Complexity: 515

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C(C=C2C(=O)CC3=C(C1)C(=C(C=C3)OC)OC)OC)OC
• Description: This alkaloid, sometimes referred to as cryptopalmine, occurs in Papaver nudi-cauZe L. and in Argernone rnunita Dur. & Hilg. subsp. rotunda. When crystallized from Me2CO it forms clusters of colourless crystals. It furnishes a crystalline hydriodide, m.p. 176-7°C (dec.) and a methiodide, m.p. 192-4°C. The struc_x0002_ture has been deduced from the mass spectrum and confirmed by synthesis.

Technology Process of Muramine

There total 10 articles about Muramine 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: 71.0%

Dihydromuramin (93264-43-8,112420-03-8) → Muramin (2292-20-8)

Guidance literature:

With sodium acetate; pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/jo071038y

Reference yield:

1-(2-bromo-4,5-dimethoxybenzyl)-7,8-dimethoxy-3-methyl-1,2,4,5-tetrahydro-3H-3-benzazepin-2-one (952196-37-1) → Muramin (2292-20-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 26 percent / P₂O₅; POCl₃ / 2 h / Heating

2: 99 percent / Rose Bengal; O₂ / methanol; CH₂Cl₂ / 0.25 h / 18 °C / UV-irradiation

3: 17 percent / LiAlH₄ / tetrahydrofuran / 20 h / Heating

4: 71 percent / NaOAc; pyridinium chlorochromate / CH₂Cl₂ / 2 h / 20 °C

With lithium aluminium tetrahydride; oxygen; sodium acetate; phosphorus pentoxide; rose bengal; pyridinium chlorochromate; trichlorophosphate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo071038y

Reference yield:

11-bromo-2,3,8,9-tetramethoxy-5,6,7,12-tetrahydroindeno[2,1-a][3]benzazepine (952196-32-6) → Muramin (2292-20-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / Rose Bengal; O₂ / methanol; CH₂Cl₂ / 0.25 h / 18 °C / UV-irradiation

2: 17 percent / LiAlH₄ / tetrahydrofuran / 20 h / Heating

3: 71 percent / NaOAc; pyridinium chlorochromate / CH₂Cl₂ / 2 h / 20 °C

With lithium aluminium tetrahydride; oxygen; sodium acetate; rose bengal; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo071038y

upstream raw materials:

Dihydromuramin

1-(2-bromo-4,5-dimethoxybenzyl)-7,8-dimethoxy-3-methyl-1,2,4,5-tetrahydro-3H-3-benzazepin-2-one

11-bromo-2,3,8,9-tetramethoxy-5,6,7,12-tetrahydroindeno[2,1-a][3]benzazepine

12-bromo-7-methyl-2,3,9,10-tetramethoxy-5,6,7,8,13,14-hexahydrodibenz[c,g]azecine-8,14-dione

Downstream raw materials:

α-allocryptopine methiodide

Refernces

• 1、 Wada, Yasuhiro,Kaga, Harumi,Uchiito, Shiho,Kumazawa, Eri,Tomiki, Miho,Onozaki, Yu,Kurono, Nobuhito,Tokuda, Masao,Ohkuma, Takeshi,Orito, Kazuhiko. "On the synthesis of protopine alkaloids". . p. 7301 - 7306. Retrieved 2008/02/11.