3-Acetyl-2,2-dimethylcyclobutane-1-carbaldehyde

Base Information

• Chemical Name: 3-Acetyl-2,2-dimethylcyclobutane-1-carbaldehyde
• CAS No.: 132478-08-1
• Molecular Formula: C9H14O2
• Molecular Weight: 154.20626
• DSSTox Substance ID: DTXSID90560880
• Nikkaji Number: J975.734A
• Mol file: 132478-08-1.mol

Synonyms:132478-08-1;3-Acetyl-2,2-dimethylcyclobutane-1-carbaldehyde;Cyclobutanecarboxaldehyde, 3-acetyl-2,2-dimethyl- (9CI);DTXSID90560880;cis-3-acetyl-2,2-dimethylcyclobutylcarbaldehyde

Chemical Property of 3-Acetyl-2,2-dimethylcyclobutane-1-carbaldehyde

Chemical Property:

• PSA: 34.14000
• LogP: 1.43660
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 154.099379685
• Heavy Atom Count: 11
• Complexity: 194

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1CC(C1(C)C)C=O

Technology Process of 3-Acetyl-2,2-dimethylcyclobutane-1-carbaldehyde

There total 4 articles about 3-Acetyl-2,2-dimethylcyclobutane-1-carbaldehyde 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:

(+)-α-pinene (7785-70-8,25766-18-1) → cis-pinononic aldehyde (132478-08-1,177316-72-2) + C8H12O2

Guidance literature:

(+)-α-pinene; With ferrous(II) sulfate heptahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ozone; In methanol; water; at -78 - 20 ℃; for 0.0833333h;

With magnesium bis(monoperoxyphthalate)hexahydrate; In methanol; water; at 0 ℃; for 2h; Overall yield = 67 percent; Overall yield = 190 mg;

DOI:10.1002/anie.201913201

Reference yield:

(1S,3S)-3-acetyl-2,2-dimethylcyclobutaneacetaldehyde1,6-cyclodecanedione (71628-89-2) → cis-pinononic aldehyde (132478-08-1,177316-72-2)

Guidance literature:

Multi-step reaction with 2 steps

1: (C₂H₅)3N, 4-dimethylaminopyridine / 1) 0 deg C, 1 h, 2) 25 deg C, 24 h

2: 1) O₃, 2) (CH₃)2S / 1) CH₂Cl₂, -78 deg C, 3 h, 2) 25 deg C, overnight

With dmap; dimethylsulfide; ozone; triethylamine;

DOI:10.1080/00397919608003550

Reference yield:

(-)-α-pinene (7785-26-4,25766-18-1) → cis-pinononic aldehyde (132478-08-1,177316-72-2)

Guidance literature:

With potassium permanganate; acetone;

upstream raw materials:

(-)-α-pinene

(1R,3S)-(+)-cis-3-acetyl-1-(2-acetoxyethenyl)-2,2-dimethylcyclobutane

(1S,3S)-3-acetyl-2,2-dimethylcyclobutaneacetaldehyde1,6-cyclodecanedione

(+)-α-pinene

Downstream raw materials:

(+)-cis-pinononoic acid

1-((1S)-2,2,3c-trimethyl-cyclobut-r-yl)-ethanone

1-((1S,3R)-3-Hydroxymethyl-2,2-dimethyl-cyclobutyl)-ethanone