Megaphone

Base Information

• Chemical Name: Megaphone
• CAS No.: 64332-37-2
• Molecular Formula: C₂₂H₃₀O₆
• Molecular Weight: 390.477
• UNII: 8J0BV7D5N9
• DSSTox Substance ID: DTXSID80214542
• Wikipedia: Megaphone_(molecule)
• Wikidata: Q6808812
• Metabolomics Workbench ID: 69509
• Mol file: 64332-37-2.mol

Synonyms:Megaphone;(-)-Megaphone;64332-37-2;NSC-288408;UNII-8J0BV7D5N9;8J0BV7D5N9;Cytotoxic neolignan from aniba megaphylla;(4R,6R)-6-[(1R,2S)-1-hydroxy-1-(3,4,5-trimethoxyphenyl)propan-2-yl]-4-methoxy-6-prop-2-enylcyclohex-2-en-1-one;2-Cyclohexen-1-one, 6-((1S,2R)-2-hydroxy-1-methyl-2-(3,4,5-trimethoxyphenyl)ethyl)-4-methoxy-6-(2-propen-1-yl)-, (4R,6R)-;Megaphone (molecule);AC1L9DME;CHEBI:6720;DTXSID80214542;Q6808812;2-Cyclohexen-1-one, 6-[2-hydroxy-1-methyl-2-(3,4,5-trimethoxyphenyl)ethyl]-4-methoxy-6-(2-propenyl)-, [4R-[4.alpha.,6.alpha.(1S*,2R*)]]-

Chemical Property of Megaphone

Chemical Property:

• Vapor Pressure: 1.17E-11mmHg at 25°C
• Boiling Point: 520.4°C at 760 mmHg
• PKA: 13.59±0.20(Predicted)
• Flash Point: 173.6°C
• PSA: 74.22000
• Density: 1.14g/cm³
• LogP: 3.48840
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 390.20423867
• Heavy Atom Count: 28
• Complexity: 547

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C1=CC(=C(C(=C1)OC)OC)OC)O)C2(CC(C=CC2=O)OC)CC=C
• Isomeric SMILES: C[C@H]([C@H](C1=CC(=C(C(=C1)OC)OC)OC)O)[C@]2(C[C@H](C=CC2=O)OC)CC=C

Technology Process of Megaphone

There total 19 articles about Megaphone 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%

Methanesulfonic acid (2R,3S,3aR,5R,6S)-3a-allyl-7a-hydroxy-5-methoxy-3-methyl-2-(3,4,5-trimethoxy-phenyl)-octahydro-benzofuran-6-yl ester → d,l-megaphone (64332-37-2,78148-79-5,96895-52-2,106973-35-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene; room temp., 3 h, then 60 deg C, 2 h;

DOI:10.1016/S0040-4039(00)86382-0

Reference yield: 46.0%

(S)-2-((1R,5R)-1-Allyl-5-methoxy-2-oxo-cyclohex-3-enyl)-propionaldehyde (96851-93-3) + 1-lithio-3,4,5-trimethoxybenzene (81952-68-3) → (-)-Isomegaphone (96895-52-2) + (-)-Megaphone (64332-37-2)

Guidance literature:

In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 ℃;

DOI:10.1016/S0040-4039(00)61960-3

Reference yield:

(2β,3β,3aα,5β)-3,3a,4,5-tetrahydro-5-methoxy-3-methyl-3a-(2-propenyl)-2-(3,4,5-trimethoxyphenyl)-6(2H)-benzofuranone (76202-43-2,78108-41-5,90898-97-8,112455-82-0,137491-87-3) → d,l-megaphone (64332-37-2,78148-79-5,96895-52-2,106973-35-7)

Guidance literature:

With diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; Yield given. Multistep reaction; 1.) THF, hexane, 45 min, 2.) THF, -55 - -60 deg C, 15 min;

DOI:10.1021/ja00400a039

upstream raw materials:

(2β,3β,3aα,5β)-3,3a,4,5-tetrahydro-5-methoxy-3-methyl-3a-(2-propenyl)-2-(3,4,5-trimethoxyphenyl)-6(2H)-benzofuranone

(2β,3β,3aα,5β)-3,3a,4,5-tetrahydro-5-methoxy-3-methyl-3a-<3-<(methylsulfonyl)oxy>propyl>-2-(3,4,5-trimethoxyphenyl)-6(2H)-benzofuranone

(2R,3S,3aR,5R,6S)-3a-Allyl-5-methoxy-3-methyl-2-(3,4,5-trimethoxy-phenyl)-hexahydro-benzofuran-6,7a-diol

(2R,3S,3aR,5R,6S)-3a-Allyl-5,6-dimethoxy-3-methyl-2-(3,4,5-trimethoxy-phenyl)-hexahydro-benzofuran-7a-ol

Downstream raw materials:

(4R,6R)-6-Allyl-4-methoxy-6-[(S)-1-methyl-2-oxo-2-(3,4,5-trimethoxy-phenyl)-ethyl]-cyclohex-2-enone