Macelignan

Base Information

• Chemical Name: Macelignan
• CAS No.: 107534-93-0
• Molecular Formula: C₂₀H₂₄O₄
• Molecular Weight: 328.408
• Hs Code.: 29329990
• UNII: 8PP3614Z43
• DSSTox Substance ID: DTXSID00148077
• Nikkaji Number: J1.069.117F
• Wikipedia: Macelignan
• Wikidata: Q6723225
• NCI Thesaurus Code: C92606
• Metabolomics Workbench ID: 129679
• ChEMBL ID: CHEMBL254071
• Mol file: 107534-93-0.mol

Synonyms:macelignan

Chemical Property of Macelignan

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 70-71℃
• Refractive Index: 1.574
• Boiling Point: 466.966 °C at 760 mmHg
• PKA: 10.19±0.20(Predicted)
• Flash Point: 236.213 °C
• PSA: 47.92000
• Density: 1.159 g/cm³
• LogP: 4.18690
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 328.16745924
• Heavy Atom Count: 24
• Complexity: 388

Purity/Quality:

98% ^*data from raw suppliers

Anwuligan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC1=CC2=C(C=C1)OCO2)C(C)CC3=CC(=C(C=C3)O)OC
• Isomeric SMILES: C[C@H](CC1=CC2=C(C=C1)OCO2)[C@@H](C)CC3=CC(=C(C=C3)O)OC

Technology Process of Macelignan

There total 10 articles about Macelignan 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:

(+)-chicanine (78919-28-5) → Macelignan (114761-92-1,107534-93-0,130008-79-6) + desoxyenshicine (59985-35-2,80483-35-8,93780-83-7,117142-09-3)

Guidance literature:

With hydrogen; palladium(II) oxide; In ethanol; at 60 - 70 ℃; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Reference yield:

C27H30O4 → erythro-austrobailignan-6 (107534-93-0,130008-79-6)

Guidance literature:

With palladium on activated charcoal; hydrogen; In tetrahydrofuran; at 20 ℃; for 10h;

DOI:10.1002/chem.202100804

Reference yield:

threo-austrobailignan-5 (55890-23-8) → (8R,8'R)-3'-methoxy-3,4-methylenedioxylignan-4'-ol (55890-24-9,107534-93-0,130008-79-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 0.35 g / NaH / dimethylformamide / 1 h / Heating

2: K₂CO₃ / acetone / 6 h / Heating

3: 1 N MeOH-HCl / 0.5 h / Heating

With hydrogenchloride; methanol; sodium hydride; potassium carbonate; In N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00292a010

upstream raw materials:

threo-austrobailignan-5

5-((2R,3R)-4-Benzo[1,3]dioxol-5-yl-2,3-dimethyl-butyl)-2-p-tolylsulfanylmethoxy-phenol

(+)-chicanine

1,2-(methylenedioxy)-4-bromobenzene

Downstream raw materials:

terameprocol

Refernces

• 1、 Rao, Koppaka V.,Chattopadhyay, Sunil K.. "Regioselective Cleavage of the Methylenedioxy Group: Conversion of (-)-Austrobailignan-5 to (-)-Dihydroguaiaretic Acid". . p. 1427 - 1429. Retrieved 2007/10/02.