Cyclobutanecarboxylic acid, 3-acetyl-2,2-dimethyl-, cis-

Base Information

• Chemical Name: Cyclobutanecarboxylic acid, 3-acetyl-2,2-dimethyl-, cis-
• CAS No.: 28587-41-9
• Molecular Formula: C9H14O3
• Molecular Weight: 170.208
• DSSTox Substance ID: DTXSID70442670
• Nikkaji Number: J811.029H
• Wikidata: Q82260078
• Mol file: 28587-41-9.mol

Synonyms:(+-)-2.2-Dimethyl-3c-acetyl-cyclobutan-carbonsaeure-(1r);(+-)-cis-Pinononsaeure;(+-)-cis-pinononoic acid;cis-(2,2-dimethyl-3-acetylcyclobutyl)formic acid;cis-3-acetyl-2,2-dimethylcyclobutylmethanoic acid;cis-nor-pinonic acid;(1R,3S)-3-Acetyl-2,2-dimethyl-cyclobutanecarboxylic acid;

Chemical Property of Cyclobutanecarboxylic acid, 3-acetyl-2,2-dimethyl-, cis-

Chemical Property:

• PSA: 54.37000
• LogP: 1.32230
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 170.094294304
• Heavy Atom Count: 12
• Complexity: 230

Purity/Quality:

(1S,3R)-3-Acetyl-2,2-dimethylcyclobutane-1-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1CC(C1(C)C)C(=O)O
• Isomeric SMILES: CC(=O)[C@@H]1C[C@@H](C1(C)C)C(=O)O

Technology Process of Cyclobutanecarboxylic acid, 3-acetyl-2,2-dimethyl-, cis-

There total 10 articles about Cyclobutanecarboxylic acid, 3-acetyl-2,2-dimethyl-, cis- 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: 79.0%

apoverbenone (1123-46-2) → cis-3-acetyl-2,2-dimethylcyclobutylmethanoic acid (28587-41-9)

Guidance literature:

With potassium permanganate; silica gel; In benzene;

DOI:10.1021/jo00392a041

Reference yield:

(+)-α-pinene (7785-70-8,25766-18-1) → cis-3-carboxy-2,2-dimethylcyclobutylmethanoic acid (3211-48-1) + cis-3-acetyl-2,2-dimethylcyclobutylmethanoic acid (28587-41-9) + cis-pinonic acid (17879-35-5,52305-34-7,61376-92-9,61826-55-9,64396-97-0,127062-09-3,473-72-3) + cis-pinic acid (473-73-4,13977-05-4,28664-02-0,61264-12-8,61774-58-1,106454-26-6,116908-81-7)

Guidance literature:

With ozone; at 24.85 ℃; under 740 Torr; Product distribution;

DOI:10.1021/es990445r

Reference yield:

(1R,5R)-(+)-β-pinene (127-91-3,25719-60-2) → cis-3-carboxy-2,2-dimethylcyclobutylmethanoic acid (3211-48-1) + cis-3-acetyl-2,2-dimethylcyclobutylmethanoic acid (28587-41-9) + cis-pinonic acid (17879-35-5,52305-34-7,61376-92-9,61826-55-9,64396-97-0,127062-09-3,473-72-3) + cis-pinic acid (473-73-4,13977-05-4,28664-02-0,61264-12-8,61774-58-1,106454-26-6,116908-81-7)

Guidance literature:

With ozone; at 24.85 ℃; under 740 Torr; Product distribution;

DOI:10.1021/es990445r

upstream raw materials:

(+)-cis-pinononoic acid

verbenone

3c-isopropenyl-2,2-dimethyl-cyclobutane-r-carbaldehyde

apoverbenone

Downstream raw materials:

trans-(2,2-dimethyl-3-acetylcyclobutyl)formic acid

Refernces

• 1、 Ferreira, J. Tercio B.,Cruz, W. O.,Vieira, P. C.,Yonashiro, M.. "Carbon-Carbon Double Bond Cleavage Using Solid-Supported Potassium Permanganate on Silica Gel". . p. 3698 - 3699. Retrieved 2007/10/02.