(-)-Clausenamide

Base Information

• Chemical Name: (-)-Clausenamide
• CAS No.: 103541-15-7
• Molecular Formula: C₁₈H₁₉NO₃
• Molecular Weight: 297.354
• Wikidata: Q105305116
• Metabolomics Workbench ID: 48290
• Mol file: 103541-15-7.mol

Synonyms:( )-Clausenamide;(-)-Clausenamide;(+/-)-Clausenamide;SCHEMBL8161624

Chemical Property of (-)-Clausenamide

Chemical Property:

• Vapor Pressure: 3.91E-12mmHg at 25°C
• Refractive Index: 1.633
• Boiling Point: 531.7 °C at 760 mmHg
• PKA: 12.93±0.60(Predicted)
• Flash Point: 275.3 °C
• PSA: 60.77000
• Density: 1.27 g/cm³
• LogP: 1.64320
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 297.13649347
• Heavy Atom Count: 22
• Complexity: 388

Purity/Quality:

98%,99%, ^*data from raw suppliers

CLAUSENAMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(C(C(C1=O)O)C2=CC=CC=C2)C(C3=CC=CC=C3)O

Technology Process of (-)-Clausenamide

There total 12 articles about (-)-Clausenamide 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: 92.0%

(+/-)‐clausenamidone → (+/-)-clausenamide (103541-15-7,104973-66-2,109905-95-5,110414-73-8,114528-76-6,114528-82-4,119616-14-7,126720-48-7,134052-81-6,134052-82-7)

Guidance literature:

With sodium tetrahydroborate; In methanol;

DOI:10.1039/b901965k

Reference yield:

phenylmagnesium bromide → (+/-)-clausenamide (103541-15-7,104973-66-2,109905-95-5,110414-73-8,114528-76-6,114528-82-4,119616-14-7,126720-48-7,134052-81-6,134052-82-7)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran / 1 h / 0 - 5 °C

2: trifluoroacetic anhydride, DMSO / CH₂Cl₂ / 1.5 h / -60 °C

3: LiB(Et)3H / tetrahydrofuran / 1 h / 0 °C

4: 1.) LDA, HMPT, 2.) P(OEt)3, O₂ / 1.) THF, hexane, from -70 to -60 deg C, 1 h, 2.) THF, hexane, -70 deg C

With N,N,N,N,N,N-hexamethylphosphoric triamide; oxygen; lithium triethylborohydride; dimethyl sulfoxide; trifluoroacetic anhydride; lithium diisopropyl amide; triethyl phosphite; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00228a037

Reference yield:

5,5-Diethoxycarbonyl-4-phenylpyrrolidin-2-one (13992-75-1) → (+/-)-clausenamide (103541-15-7,104973-66-2,109905-95-5,110414-73-8,114528-76-6,114528-82-4,119616-14-7,126720-48-7,134052-81-6,134052-82-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) NaH / 1.) DMF, RT, 2.) DMF, RT, 1 h

2: aq. Ba(OH)2 / ethanol / 0.33 h / 70 °C

3: 170 °C

4: 89.2 percent / LiB(Et)3H / tetrahydrofuran / 1 h / 0 °C

5: trifluoroacetic anhydride, DMSO / CH₂Cl₂ / 1.5 h / -60 °C

6: tetrahydrofuran / 1 h / 0 - 5 °C

7: trifluoroacetic anhydride, DMSO / CH₂Cl₂ / 1.5 h / -60 °C

8: LiB(Et)3H / tetrahydrofuran / 1 h / 0 °C

9: 1.) LDA, HMPT, 2.) P(OEt)3, O₂ / 1.) THF, hexane, from -70 to -60 deg C, 1 h, 2.) THF, hexane, -70 deg C

With N,N,N,N,N,N-hexamethylphosphoric triamide; barium dihydroxide; oxygen; sodium hydride; lithium triethylborohydride; dimethyl sulfoxide; trifluoroacetic anhydride; lithium diisopropyl amide; triethyl phosphite; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/jo00228a037

upstream raw materials:

(+/-)-(4R^*,5R^*,7S^*)-5-(α-hydroxybenzyl)-1-methyl-4-phenylpyrrolidin-2-one

5,5-Diethoxycarbonyl-4-phenylpyrrolidin-2-one

(+/-)-(4R^*,5R^*)-5-formyl-1-methyl-4-phenylpyrrolidin-2-one

(+/-)-(4R^*,5R^*)-5-(hydroxymethyl)-1-methyl-4-phenylpyrrolidin-2-one

Downstream raw materials:

(±)-(3R,4S,5S,6R)-clausenamide

Refernces

• 1、 Hartwig, Wolfgang,Born, Liborius. "Diastereoselective and Enantioselective Total Synthesis of the Hepatoprotective Agent Clausenamide". . p. 4352 - 4358. Retrieved 2007/10/02.