Spiro[2.3]hexane-1-carboxylic Acid

• CAT Number: M087308
• CAS Number: 17202-56-1
• Molecular Formula: C7H10O2
• Molecular Weight: 126.155
• Purity: ≥95%
• Storage: Store at -20C
• IUPAC Name: spiro[2.3]hexane-2-carboxylic acid
• InChI: InChI=1S/C7H10O2/c8-6(9)5-4-7(5)2-1-3-7/h5H,1-4H2,(H,8,9)
• InChIKey: VVSCGNLRDCLHAN-UHFFFAOYSA-N
• SMILES: C1CC2(C1)CC2C(=O)O

[1]. Yashin, N.V., Averina, E.B., Vasilenko, D.A., Grishin, Y.K., Osolodkin, D.I., Palyulin, V.A., Kuznetsova, T.S. and Zefirov, N.S., 2017.
Synthesis of novel non-natural spiro [2.3] hexane amino acids, the conformationally restricted analogs of γ-aminobutyric acid.
Abstract: 3-Methylenecyclobutanecarboxylic acid and its methyl ester were used as the starting compounds for the synthesis of new spiro[2.3]hexane amino acids, the conformationally rigid analogs of γ-aminobutyric acid, namely, 5-aminospiro[2.3]hexanecarboxylic and 5-amino-spiro[2.3]hexanephosphonic acids, promising modulators of GABAergic cascades in the human central nervous system. The methods developed for the synthesis of the target amino acids are based on the reactions of catalytic [1+2] cycloaddition of diazoacetic and diazophosphonic esters to 3-substituted methylenecyclobutanes, as well as on a modified Curtius reaction for the transformation of a carboxy group to the amine one.
Russian Chemical Bulletin, 66(8), pp.1483-1490.

[2]. Yashin, N.V., Averina, E.B., Gerdov, S.M., Kuznetsova, T.S. and Zefirov, N.S., 2003.
Catalytic cyclopropanation of methylenecyclobutanes using ethyl nitrodiazoacetate.
Abstract: The reaction of ethyl nitrodiazoacetate with a series of methylenecyclobutanes was studied and both [1+2]- and [2+3]-cycloaddition pathways were observed depending on olefin structure. Amino acids of a spirohexane type were synthesized from methylenecyclobutanes by a three-step synthesis. The reaction of ethyl nitrodiazoacetate with the series of methylenecyclobutanes was studied and both [1+2]- and [2+3]-cycloaddition pathways were observed depending on olefin structure. Amino acids of a spirohexane type were synthesized from methylenecyclobutanes by a three-step synthesis.
Synthesis of spirohexane amino acids. Tetrahedron letters, 44(45), pp.8241-8244.