Pentacyclo[4.2.0.02,5.03,8.04,7]octane-1,4-dicarboxaldehyde

Base Information

• Chemical Name: Pentacyclo[4.2.0.02,5.03,8.04,7]octane-1,4-dicarboxaldehyde
• CAS No.: 163332-89-6
• Molecular Formula: C10H8 O2
• Molecular Weight: 160.172
• DSSTox Substance ID: DTXSID40467178
• Wikidata: Q82293989
• Mol file: 163332-89-6.mol

Synonyms:Cubane-1,4-dicarbaldehyde;163332-89-6;Pentacyclo[4.2.0.02,5.03,8.04,7]octane-1,4-dicarboxaldehyde;Pentacyclo[4.2.0.02,5.03,8.04,7]octane-1,4-dicarboxaldehyde (9CI);1,4-cubanedicarboxaldehyde;DTXSID40467178;CUBANE-1,8-DICARBALDEHYDE;Pentacyclo[4.2.0.02,5.03,8.04,7]octane-1,4-dicarboxaldehyde(9ci)

Chemical Property of Pentacyclo[4.2.0.02,5.03,8.04,7]octane-1,4-dicarboxaldehyde

Chemical Property:

• PSA: 34.14000
• LogP: 0.12220
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 160.052429494
• Heavy Atom Count: 12
• Complexity: 281

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(=O)C12C3C4C1C5C2C3C45C=O

Technology Process of Pentacyclo[4.2.0.02,5.03,8.04,7]octane-1,4-dicarboxaldehyde

There total 2 articles about Pentacyclo[4.2.0.02,5.03,8.04,7]octane-1,4-dicarboxaldehyde 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:

cubane-1,4-dicarboxylic acid dimethyl ester (29412-62-2) → cubane-1,4-dicarboxaldehyde (163332-89-6)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 17 h / 20 °C / Reflux

2: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.25 h / 0 °C / Inert atmosphere; Molecular sieve

With lithium aluminium tetrahydride; tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane;

DOI:10.1002/chem.201805124

Reference yield:

1,4-bis(hydroxymethyl)cubane (60462-27-3) → cubane-1,4-dicarboxaldehyde (163332-89-6)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; Yield given. Multistep reaction; 1.) CH₂Cl₂, from -20 to -15 deg C, 1.5 h, 2.) CH₂Cl₂, RT, 10 min;

DOI:10.1021/ja00096a016

upstream raw materials:

1,4-bis(hydroxymethyl)cubane

cubane-1,4-dicarboxylic acid dimethyl ester

Refernces

• 1、 Houston, Sevan D.,Xing, Hui,Bernhardt, Paul V.,Vanden Berg, Timothy J.,Tsanaktsidis, John,Savage, G. Paul,Williams, Craig M.. "Cyclooctatetraenes through Valence Isomerization of Cubanes: Scope and Limitations". supporting information. p. 2735 - 2739. Retrieved 2019/02/07.