10481-25-1

Usage

Uses

Due to the limited information available about the specific uses, applications, or hazards of spiro[3.3]heptane-2,6-dicarboxylic acid monomethyl ester, it is primarily used in scientific research and experimentation. However, based on its chemical properties and reactivity, it may have potential applications in various industries, such as:
Used in Chemical Research Industry:
Spiro[3.3]heptane-2,6-dicarboxylic acid monomethyl ester is used as a research compound for studying its chemical properties, reactivity, and potential applications in various chemical reactions and processes.
Used in Pharmaceutical Industry:
Although not explicitly mentioned, due to its unique structure and reactivity, spiro[3.3]heptane-2,6-dicarboxylic acid monomethyl ester may be used as an intermediate or building block in the synthesis of pharmaceutical compounds, potentially contributing to the development of new drugs.
Used in Material Science:
The unique structure and properties of spiro[3.3]heptane-2,6-dicarboxylic acid monomethyl ester may also find applications in the development of new materials with specific properties, such as polymers, coatings, or adhesives, by serving as a monomer or a component in their synthesis.

Upstream product

• 3057-91-8 spiro[3.3]heptane-2,6-dicarboxylic acid 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 27259-79-6 dimethyl spiro[3.3]heptane-2,6-dicarboxylate 

Downstream Products

• 170508-14-2 (+/-)-2-carbomethoxy-6-<(N-tert-butoxycarbonyl)amino>spiro<3.3>heptane 

Relevant academic research and scientific papers

(±)-N9-(2-(hydroxymethyl)spiro[3.3]hept-6-yl)adenine. The first biologically active saturated analogue of adenallene with axial dissymmetry

Synthesis of the title analogue 2 is described. Fecht's acid (3) was esterified with N,N-dimethylformamide dimethyl acetal to give monoester 4 along with diester 5. Compound 4 was transformed to ester amide 6 by the reaction with isobutyl chloroformate and triethylamine followed by ammonolysis. Hoffman rearrangement of 6 effected by lead tetraacetate in tert-butyl alcohol led to the N-tert-butoxycarbonyl ester 7. The latter was reduced with Ca(BH4)2 to give the protected amino alcohol 8. Removal of the N-tert-butoxycarbonyl group with 2 M HCl in methanol afforded the hydrochloride of amino alcohol 2. Reaction of 9 with 5-amino-4,6-dichloropyrimidine and triethylamine gave the pyrimidine derivative 10 which, in turn, was cyclized to 6-chloropurine 11a. Ammonolysis of the latter intermediate afforded the title analogue 2. The 1H NMR spectrnm of Fecht's acid (3) in CD3COCD3 showed that four methylene protons were magnetically nonequivalent (two quartets) whereas the other four were equivalent, forming a single doublet. Compound 2 inhibited the replication of human cytomegalovirus (IC50 32 μM) and growth of murine leukemia L1210 cells (IC50 30 μM). Zone assays showed inhibition of the following tumor cultures at 0.5 mg/disk: murine leukemia P388, mouse tumors PO3, C38, and M17/Adr as well as human tumors MCF-7 and CX-1.

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.