27259-79-6

Basic information

• Product Name: dimethyl spiro[3.3]heptane-2,6-dicarboxylate
• Synonyms: dimethyl spiro[3.3]heptane-2,6-dicarboxylate;(+)-Spiro[3.3]heptane-2,6-dicarboxylic acid dimethyl ester
• CAS NO: 27259-79-6
• Molecular Formula: C₁₁H₁₆O₄
• Molecular Weight: 212.24234
• Mol File: 27259-79-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 264℃
• Flash Point: 124℃
• Appearance: /
• Density: 1.17
• CAS DataBase Reference: dimethyl spiro[3.3]heptane-2,6-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl spiro[3.3]heptane-2,6-dicarboxylate(27259-79-6)
• EPA Substance Registry System: dimethyl spiro[3.3]heptane-2,6-dicarboxylate(27259-79-6)

Safety Data

• Hazardous Substances Data: 27259-79-6(Hazardous Substances Data)

Usage

General Description

Dimethyl spiro[3.3]heptane-2,6-dicarboxylate is a chemical compound that can be synthesized through the esterification of the corresponding diacid. It is a white solid with a molecular formula of C12H18O4. dimethyl spiro[3.3]heptane-2,6-dicarboxylate is commonly used as a building block in organic synthesis and pharmaceutical research. It has been found to have potential applications in the development of new drugs and pharmaceuticals due to its unique structure and reactivity. Additionally, dimethyl spiro[3.3]heptane-2,6-dicarboxylate has been investigated for its potential use in materials science, such as in the development of new polymers and advanced materials.

Upstream product

• 3057-91-8 spiro[3.3]heptane-2,6-dicarboxylic acid 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 67-56-1 methanol 
• 52097-87-7 spiro[3.3]heptane-2,6-dicarbonyl dichloride 

Downstream Products

• 858801-94-2 2,6-di(diphenylhydroxymethyl)spiro[3.3]heptane 
• 10481-25-1 Methyl-hydrogen-spiro<3.3>heptan-2,6-dicarboxylat 
• 3057-91-8 spiro[3.3]heptane-2,6-dicarboxylic acid 

Relevant articles and documents

Cyclobutane-derived diamines: Synthesis and molecular structure

Cyclobutane diamines (i.e., cis- and trans-1,3-diaminocyclobutane, 6-amino-3-azaspiro[3.3]heptane, and 3,6-diaminospiro[3.3]heptane) are considered as promising sterically constrained diamine building blocks for drug discovery. An approach to the syntheses of their Boc-monoprotected derivatives has been developed aimed at the preparation of multigram amounts of the compounds. These novel synthetic schemes exploit classical malonate alkylation chemistry for the construction of cyclobutane rings. The conformational preferences of the cyclobutane diamine derivatives have been evaluated by X-ray diffraction and compared with the literature data on sterically constrained diamines, which are among the constituents of commercially available drugs.

Enantiopure spiro[3.3]heptane-2,6-dicarboxylic acid

Using chiral HPLC and 13C NMR analyses, the optical purity of (+)-spiro[3.3]heptane-2,6-dicarboxylic acid (1) obtained by the known diastereomer method with brucine was first clarified to be 90% e.e., which was conventionally considered to be 100% e.e. Among the ester derivatives synthesized, dicinnamyl spiro[3.3]heptane-2,6-dicarboxylate (2) was found to show high optical separation ability on the chiral HPLC with cellulose phenyl carbamate stationary phase eluting with hexane/2-propanol (10/1, v/v) at a flow rate of 0.4 ml/min at 35 °C (separation factor, α, 1.14), and the isolated optically pure (+)- and (-)-2 show [α]D26 of +1.84° (c = 1.74, CHCl3) and -1.84° (c = 1.74, CHCl3), respectively. Acidic hydrolysis of optically pure (+)-/(-)-2 without racemization yielded optically pure (+)-/(-)-1, exhibiting [φ]40527 = +21.1° ([φ]D27 = +9.1°) (c = 5.33, acetone) and [φ]40527 = -21.1° ([φ]D27 = -9.1°) (c = 5.32, acetone), respectively.