Pallavicinin

Base Information

• Chemical Name: Pallavicinin
• CAS No.: 156250-64-5
• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 330.424
• Wikidata: Q105322447
• Mol file: 156250-64-5.mol

Synonyms:neopallavicinin;pallavicinin

Chemical Property of Pallavicinin

Chemical Property:

• Vapor Pressure: 8.62E-09mmHg at 25°C
• Boiling Point: 464.1°C at 760 mmHg
• Flash Point: 203.2°C
• PSA: 52.60000
• Density: 1.212g/cm³
• LogP: 3.06910
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 330.18310931
• Heavy Atom Count: 24
• Complexity: 690

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C1C2C(C3C4(CC(C3(O2)C)C(=O)C(C4C=C)(C)C)C)OC1=O
• Isomeric SMILES: C/C=C\1/[C@H]2[C@H]([C@@H]3[C@@]4(C[C@H]([C@@]3(O2)C)C(=O)C([C@@H]4C=C)(C)C)C)OC1=O

Technology Process of Pallavicinin

There total 24 articles about Pallavicinin 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: 55.0%

C18H24O4 + acetaldehyde (75-07-0,9002-91-9) → (-)-pallavicinin (156250-64-5)

Guidance literature:

C₁₈H₂₄O₄; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

acetaldehyde; In tetrahydrofuran-d8; at -78 ℃; for 1.5h; Inert atmosphere;

With dmap; methanesulfonyl chloride; triethylamine; In dichloromethane; at 20 ℃; for 8h; enantioselective reaction; Inert atmosphere;

DOI:10.1002/anie.201506575

Reference yield: 12.0%

C18H24O4 + acetaldehyde (75-07-0,9002-91-9) → (+)-neopallavicinin (156250-64-5)

Guidance literature:

C₁₈H₂₄O₄; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

acetaldehyde; In tetrahydrofuran-d8; at -78 ℃; for 1.5h; Inert atmosphere;

With dmap; methanesulfonyl chloride; triethylamine; In dichloromethane; at 20 ℃; for 8h; enantioselective reaction; Inert atmosphere;

DOI:10.1002/anie.201506575

Reference yield:

C14H18O3 → (-)-pallavicinin (156250-64-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: n-butyllithium / diethyl ether; hexane / 1 h / 0 - 20 °C / Inert atmosphere

1.2: 0.33 h / 0 °C / Inert atmosphere

2.1: lithium triethylborohydride / tetrahydrofuran / 0.08 h / 60 °C / Inert atmosphere

3.1: Dess-Martin periodane / dichloromethane / 0.5 h / 0 - 20 °C

4.1: diethyl ether; tetrahydrofuran / 0.33 h / -40 °C / Inert atmosphere

5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.83 h / 0 - 20 °C

6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 20 °C

7.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

7.2: 1.5 h / -78 °C / Inert atmosphere

7.3: 8 h / 20 °C / Inert atmosphere

With n-butyllithium; lithium triethylborohydride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 2.1: |Payne Rearrangement / 6.1: |Michael Addition;

DOI:10.1002/anie.201506575

upstream raw materials:

acetaldehyde