Cyclopropanone

• CAS: 5009-27-8
• Catalog Number: ACM5009278
• Category: Other Products
• Molecular Weight: 0
• Molecular Formula: C₃H₄O
• Synonyms: cyclopropanone

Case Study

Applications of Cyclopropanes in Natural Product Synthesis

Tang, Pei, and Yong Qin. Synthesis 44.19 (2012): 2969-2984.

Activated cyclopropanes exhibit a wide range of reactivity and are therefore powerful building blocks in organic chemistry and natural product synthesis. There are many recent applications of cyclopropane-based methods in natural product synthesis. These applications include various processes involving cyclopropanation-ring opening-cyclization or ring expansion to form key natural product skeletons. Cyclopropanes play an important role in organic synthesis. When the strained three-membered ring is properly activated, the resulting cyclopropane derivatives are valuable reactants for the rapid generation of molecular complexity. In particular, donor-acceptor (DA) cyclopropanes, doubly activated by ortho-substituted electron-donating and electron-withdrawing groups, are particularly useful synthetic intermediates because they are easily cleaved under mild conditions to form reactive 1,3-zwitterionic intermediates that can participate in a variety of reactions. Cyclopropane-based chemistry has been greatly developed over the years, and an impressive array of methods has been applied to the synthesis of complex natural products.
The tetrahydrofuran was constructed using a Lewis acid-catalyzed formal [3+2] cycloaddition of donor-acceptor cyclopropanes and β-silyloxyaldehydes and subsequently converted to (+)-polyanthraquinone A in several steps. First, intramolecular cyclopropanation of the ketoester was accomplished in two steps via an intermediate diazonium compound, followed by Cu(t-BuSal)-catalyzed cyclopropanation to afford the diactivated cyclopropane in 71% overall yield. Since aldehyde 8 was unstable to both β-elimination and aldol reactions in the presence of Lewis acids, the cyclopropane was treated in the presence of a sterically hindered MADNTf catalyst, which was formed in situ by the protolysis of MAD with triflimide (HNTf). The reaction afforded the bicyclic skeleton in 76% yield with good diastereoselectivity.

Cyclopropanone C-C Activation

Jang, Yujin, and Vincent NG Lindsay. Organic Letters 22.22 (2020): 8872-8876.

A formal [3+2] cycloaddition reaction between cyclopropanone and alkynes via Ni-catalyzed C-C bond activation has been developed, with 1-sulfonylcyclopropanol serving as a key precursor to cyclopropanone in the presence of trimethylaluminum. This transformation affords 2,3-disubstituted cyclopentenones with full regiocontrol, favoring the reverse Pauson-Khand product, in which the bulky substituent is located at the 3-position of the ring. In this process, the trimethylaluminum additive is believed to play multiple roles, including acting as a Brønsted base to trigger the equilibrium of the cyclopropanone and the release of methane, and as a source of Lewis acid to activate the carbonyl group for the nickel-catalyzed C-C activation.
1-Phenylsulfonylcyclopropanol was selected as a model substrate and first subjected to Murakami conditions at 100 °C in the presence of excess 1-phenylpropyne, Ni(cod), and PCyin toluene. No 2,3-disubstituted cyclopentenones were observed and most of the starting material was recovered under these conditions. An evaluation of various reagents that could potentially promote cyclopropanone formation without negatively interfering with catalysis identified trimethylaluminum as a key additive, generating cyclopentenone in 21% yield as a single regioisomer when the reaction was conducted at room temperature and without added ligand. As the role of trimethylaluminum remained unclear at the time, several Lewis acids such as TiCl, SnCl, BF·OEt, and organometallic reagents similar to AlMe such as EtZn were also evaluated, but none afforded the cyclopentenone product. When the reaction was conducted at 50 °C, the alkyne substrate oligomerized, and both 1-sulfonylcyclopropanol 2a and cyclopentenone 4a decomposed. The Ni(0) catalyst proved to be essential for the desired reactivity, with higher conversion efficiencies when this species was generated in situ from NiBr and Zn(0), with an optimal loading of 30 mol% each.

Custom Q&A

What is the molecular formula of Cyclopropanone?

The molecular formula of Cyclopropanone is C3H4O.

What is the molecular weight of Cyclopropanone?

The molecular weight of Cyclopropanone is 56.06 g/mol.

What is the IUPAC name of Cyclopropanone?

The IUPAC name of Cyclopropanone is cyclopropanone.

What is the InChI of Cyclopropanone?

The InChI of Cyclopropanone is InChI=1S/C3H4O/c4-3-1-2-3/h1-2H2.

What is the InChIKey of Cyclopropanone?

The InChIKey of Cyclopropanone is VBBRYJMZLIYUJQ-UHFFFAOYSA-N.

What is the Canonical SMILES of Cyclopropanone?

The Canonical SMILES of Cyclopropanone is C1CC1=O.

What is the CAS number of Cyclopropanone?

The CAS number of Cyclopropanone is 5009-27-8.

What is the XLogP3-AA value of Cyclopropanone?

The XLogP3-AA value of Cyclopropanone is -0.3.

How many hydrogen bond acceptors does Cyclopropanone have?

Cyclopropanone has 1 hydrogen bond acceptor.

Is the compound of Cyclopropanone canonicalized?

Yes, the compound of Cyclopropanone is canonicalized.