3057-91-8

Usage

Uses

Used in Pharmaceutical Industry:
Spiro[3.3]heptane-2,6-dicarboxylic acid is used as a building block for the synthesis of pharmaceuticals due to its unique molecular structure and chemical reactivity. It can be incorporated into the development of new drugs with potential therapeutic effects.
Used in Agrochemical Industry:
In the agrochemical industry, spiro[3.3]heptane-2,6-dicarboxylic acid is utilized as a key intermediate in the production of agrochemicals. Its chemical properties allow for the creation of novel compounds with potential applications in agriculture, such as pesticides and herbicides.
Used in Organic Compounds Synthesis:
Spiro[3.3]heptane-2,6-dicarboxylic acid is used as a versatile building block in the synthesis of various organic compounds. Its unique structure and reactivity enable the development of new molecules with diverse applications in different industries.
Used in Novel Materials Synthesis:
Spiro[3.3]heptane-2,6-dicarboxylic acid is used as a key component in the synthesis of novel materials, such as polymers and dyes. Its chemical properties contribute to the development of innovative materials with unique properties and potential applications in various fields.
Used in Enzyme and Receptor Inhibition:
Spiro[3.3]heptane-2,6-dicarboxylic acid has been studied for its potential as an inhibitor of certain enzymes and receptors in the human body. Its ability to modulate biological processes makes it a promising candidate for the development of new therapeutic agents targeting specific pathways in the treatment of various diseases.

InChI:InChI=1/C9H12O4/c10-7(11)5-1-9(2-5)3-6(4-9)8(12)13/h5-6H,1-4H2,(H,10,11)(H,12,13)

Upstream product

• 3229-00-3 pentaerythritol tetrabromide 
• 18424-76-5 dimethyl malonate sodium salt 
• 1071-46-1 hydrogen ethyl malonate 
• 27259-79-6 dimethyl spiro[3.3]heptane-2,6-dicarboxylate 
• 2514-70-7 pentaerythritol tetrakis(benzenesulfonate) 
• 105-53-3 diethyl malonate 
• 22290-30-8 spiro[3.3]heptane-2,2,6,6-tetracarboxylic acid 

Downstream Products

• 132616-34-3 diethyl spiro[3.3]heptane-2,6-dicarboxylate 
• 27259-79-6 dimethyl spiro[3.3]heptane-2,6-dicarboxylate 
• 10481-25-1 Methyl-hydrogen-spiro<3.3>heptan-2,6-dicarboxylat 
• 52097-91-3 (+)-2,6-dibromo-spiro[3.3]heptane-dicarboxylic acid-(2.6) 

Relevant academic research and scientific papers

Preparation and characterization of a new chiral metal-organic framework with spiranes

Herein we report the first homochiral IRMOF structure with chiral carbocyclic spirolinkers, basic Zn-(R)-spiro[3.3]heptane-2,6-dicarboxylate, named WIG-5. First, (R)-spiro[3.3]heptane-2,6-dicarboxylic acid was prepared involving a HPLC separation on chiral stationary phase, then further transformed into homochiral WIG-5 by the solvothermal reaction with zinc nitrate hexahydrate in dimethyl formamide (DMF). WIG-5 crystallizes in the P212121 space group and is built of two interpenetrated networks with pcu underlying network topology. The tetranuclear secondary building units (SBUs) of WIG-5 are coordinated to two DMF molecules and six (R)-spiro[3.3]heptane-2,6-dicarboxylic acid linkers, that results in the formation of a homochiral distorted MOF-5-like structure. Extensive characterization by single crystal X-ray diffraction, powder X-ray diffraction, polarized light microscopy, infrared microspectroscopy, solid-state vibrational circular dichroism spectroscopy and thermogravimetry/mass spectroscopy has been performed on the new material. Birefringence of large WIG-5 single crystals enables potential optical applications.

Fecht's acid revisited: A spirocyclic dicarboxylate for non-aromatic MOFs

Spiro[3.3]heptane-2,6-dicarboxylic acid (Fecht's acid, H2SHDC) is examined as a non-aromatic terephthalic acid isostere for the first time. The rigid spirocyclic backbone provides greater steric bulk than conventional aromatic dicarboxylates with consequences for pore chemistry and control of interpenetration, presented here in the structures of two new MOFs. Complex 1 is a three-dimensional rod packed structure consisting of Yb-carboxylate chains bridged by SHDC linkers which, although non-porous, exhibits a surprisingly high thermal stability for a spirocyclic cyclobutane derivative. Complex 2 is a co-ligand complex of SHDC with trans-1,2-bis(4-pyridyl)ethene (bpe) which contains linear solvent channels despite fourfold interpenetration. Although the framework does not retain its structure following evacuation, a clear difference is observed in the extended structure compared to the structurally related terephthalate species. This observation suggests the non-aromatic backbone of Fecht's acid and other rigid aliphatic linkers may prove an effective means to disfavour deleterious close inter-framework contacts which prevail in interpenetrated aromatic MOFs. This journal is

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.