1352653-03-2

Basic information

• Product Name: dimethyl 2-(1,3-dioxoisoindolin-2-yl)-cyclopropane-1,1-dicarboxylate
• Synonyms: dimethyl 2-(1,3-dioxoisoindolin-2-yl)-cyclopropane-1,1-dicarboxylate
• CAS NO: 1352653-03-2
• Molecular Weight: 303.271
• Mol File: 1352653-03-2.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: dimethyl 2-(1,3-dioxoisoindolin-2-yl)-cyclopropane-1,1-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl 2-(1,3-dioxoisoindolin-2-yl)-cyclopropane-1,1-dicarboxylate(1352653-03-2)
• EPA Substance Registry System: dimethyl 2-(1,3-dioxoisoindolin-2-yl)-cyclopropane-1,1-dicarboxylate(1352653-03-2)

Safety Data

• Hazardous Substances Data: 1352653-03-2(Hazardous Substances Data)

Upstream product

• 3485-84-5 N-vinylphthalimide 
• 6773-29-1 dimethyl diazomalonate 

Downstream Products

• 1356460-11-1 dimethyl 2-(2-(1,3-dioxoisoindolin-2-yl)-4-oxo-4-phenylbutyl)malonate 

Relevant articles and documents

An Expeditious Route to trans-Configured Tetrahydrothiophenes Enabled by Fe(OTf)3-Catalyzed [3+2] Cycloaddition of Donor–Acceptor Cyclopropanes with Thionoesters

A synthetic route to trans-configured tetrahydrothiophenes (THTs) through Fe(OTf)3-promoted [3+2] cycloaddition of donor–acceptor cyclopropanes with thionoesters was developed. The cycloaddition proceeded in high yield with high diastereoselectivity, affording transient α-alkoxy THTs. Not only aromatic and aliphatic thionoesters, but also thionolactone were applicable to the present iron catalysis. Further transformation of the S,O-ketal functionality of the product was achieved in a highly trans diastereoselective manner. Moreover, the utility of our methodology was clearly demonstrated by the synthesis of enantioenriched trans-configured THTs.

(3+2)-Cycloaddition of Donor-Acceptor Cyclopropanes with Thiocyanate: A Facile and Efficient Synthesis of 2-Amino-4,5-dihydrothiophenes

An easy and efficient route to obtain 2-amino-4,5-dihydrothiophenes is presented. A formal (3+2)-cycloaddition of donor-acceptor cyclopropanes and ammonium thiocyanate catalyzed by Yb(OTf) 3delivers the desired products in good to excellent yields. A broad range of functional groups is tolerated during this process.

Dynamic kinetic asymmetric [3 + 2] annulation reactions of aminocyclopropanes

We report the first example of a dynamic kinetic asymmetric [3 + 2] annulation reaction of aminocyclopropanes with both enol ethers and aldehydes. Using a Cu catalyst and a commercially available bisoxazoline ligand, cyclopentyl- and tetrahydrofurylamines were obtained in 69-99% yield and up to a 98:2 enantiomeric ratio using the same reaction conditions. The method gives access to important enantio-enriched nitrogen building blocks for the synthesis of bioactive compounds.