7402-61-1

Basic information

• Product Name: ETHYL 2-CYANO-2-CYCLOHEPTYLIDENACETATE
• Synonyms: Cycloheptylidenecyanoacetic acid ethyl ester;Einecs 231-006-3;ETHYL 2-CYANO-2-CYCLOHEPTYLIDENACETATE;ethyl cyanocycloheptylideneacetate;Cyano(cycloheptylidene)acetic acid ethyl ester
• CAS NO: 7402-61-1
• Molecular Formula: C₁₂H₁₇NO₂
• Molecular Weight: 207.27
• EINECS: 231-006-3
• Mol File: 7402-61-1.mol

Chemical Properties

• Boiling Point: 327.6°Cat760mmHg
• Flash Point: 154.2°C
• Appearance: /
• Density: 1.057g/cm³
• Vapor Pressure: 0.0002mmHg at 25°C
• Refractive Index: 1.49
• CAS DataBase Reference: ETHYL 2-CYANO-2-CYCLOHEPTYLIDENACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-CYANO-2-CYCLOHEPTYLIDENACETATE(7402-61-1)
• EPA Substance Registry System: ETHYL 2-CYANO-2-CYCLOHEPTYLIDENACETATE(7402-61-1)

Safety Data

• Hazardous Substances Data: 7402-61-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 2-CYANO-2-CYCLOHEPTYLIDENACETATE is used as a synthetic intermediate for the development of various pharmaceuticals. Its unique chemical structure allows it to be a key component in the creation of new drugs, contributing to the advancement of medical treatments.
Used in Agrochemical Industry:
In the agrochemical sector, ETHYL 2-CYANO-2-CYCLOHEPTYLIDENACETATE is utilized as a building block for the synthesis of different agrochemicals. Its role in this industry is crucial for the production of effective and innovative products that support agriculture and pest control.
Used as an Intermediate in Organic Compounds Production:
ETHYL 2-CYANO-2-CYCLOHEPTYLIDENACETATE is also employed as an intermediate in the synthesis of other organic compounds. Its versatility in chemical reactions makes it a valuable asset in the development of a wide range of organic substances for various applications.

InChI:InChI=1/C12H17NO2/c1-2-15-12(14)11(9-13)10-7-5-3-4-6-8-10/h2-8H2,1H3

Upstream product

• 505-48-6 octane-1,8-dioic acid 
• 105-56-6 ethyl 2-cyanoacetate 
• 502-42-1 cycloheptanone 

Downstream Products

• 7501-71-5 cyano(cycloheptyl)acetic acid ethyl ester 
• 4448-73-1 cycloheptyl-malonic acid 
• 4401-21-2 2-oxa-spiro[4.6]undecane-1,3-dione 

Relevant articles and documents

Distal γ-C(sp3)?H Olefination of Ketone Derivatives and Free Carboxylic Acids

Reported herein is the distal γ-C(sp3)?H olefination of ketone derivatives and free carboxylic acids. Fine tuning of a previously reported imino-acid directing group and using the ligand combination of a mono-N-protected amino acid (MPAA) and an electron-deficient 2-pyridone were critical for the γ-C(sp3)?H olefination of ketone substrates. In addition, MPAAs enabled the γ-C(sp3)?H olefination of free carboxylic acids to form diverse six-membered lactones. Besides alkyl carboxylic acids, benzylic C(sp3)?H bonds also could be functionalized to form 3,4-dihydroisocoumarin structures in a single step from 2-methyl benzoic acid derivatives. The utility of these protocols was demonstrated in large scale reactions and diversification of the γ-C(sp3)?H olefinated products.

PYRIMIDONE DERIVATIVES AND THEIR USE IN THE TREATMENT, AMELIORATION OR PREVENTION OF A VIRAL DISEASE

The present invention relates to a compound having the general formula (I), optionally in the form of a pharmaceutically acceptable salt, solvate, polymorph, codrug, cocrystal, prodrug, tautomer, racemate, enantiomer, or diastereomer or mixture thereof, which are useful in treating, ameloriating or preventing a viral disease, in particular influenza.

Improved synthesis of γ-lactones from cyclopropyl cyanoesters

Cyclopropyl cyanoesters 2 were reliably converted to c-lactones 4 on treatment with aqueous sulfuric acid. The cyanoesters could be easily prepared from ketones or aldehydes in two steps, making this process particularly attractive from an efficiency standpoint. Copyright

Nitrilase-catalyzed selective hydrolysis of dinitriles and green access to the cyanocarboxylic acids of pharmaceutical importance

To further explore its synthetic applications, the nitrilase bll6402 from Bradyrhizobium japonicum strain USDA110 has been examined toward the hydrolysis of various dinitriles. It has been found that nitrilase bll6402 effectively hydrolyzed α,ω-dinitriles to ω-cyanocarboxylic acids, and the selectivity was independent of the substrate chain length. This feature is distinct from all the known nitrilases of various sources. Nitrilase bll6402 was thus applied to the synthesis of 1-cyanocycloalkaneacetic acids, the useful precursors for the synthesis of gabapentin and its analogues.

Carboxylate bioisosteres of gabapentin

A series of carboxylate bioisosteres of structures related to gabapentin 1 have been prepared. When the carboxylate was replaced by a tetrazole, this group was recognized by the α2-δ protein. Further characterization of α2-δ binding compounds 14a and 14b revealed a similar pattern of functional in vitro and in vivo activity to gabapentin 1.

Antiarthritic and suppressor cell inducing activity of azaspiranes: Structure-function relationships of a novel class of immunomodulatory agents

Spirogermanium (1;8,8-diethyl-N,N-dimethyl-2-aza-8-germaspiro[4.5]decane-2-propanamin e dihydrochloride) is a potent cytotoxic agent in vitro which has demonstrated limited activity in experimental animal tumor models. Subsequently, it has been reported that spirogermanium has antiarthritic and suppressor cell-inducing activity. We have synthesized a series of substituted 8-hetero-2-azaspiro[4.5]decane and 9-hetero-3-azaspiro[5.5]undecane analogues of spirogermanium to identify the heteroatom requirements for in vivo antiarthritic and suppressor cell-inducing activity. This structure-activity relationship study has identified that appropriately substituted silicon and carbon analogues of spirogermanium retain both antiarthritic and immunosuppressive activity, with the 8,8-dipropyl (carbon) analogue being among the most active. Following the identification of N,N-dimethyl-8,8-dipropyl-2-azaspiro[4,5]decane-2-propanamine dihydrochloride (9) as more active analogue than spirogermanium, a series of 8,8-dipropyl analogues with various amine substituents were synthesized. A number of these analogues had activity similar to that of 9. A correlation between activity in the adjuvant arthritic rat and the ability to induce suppressor cells (r = 0.894, p0.001) suggests an association between the two pharmacologic effects. While the precise biochemical mechanism(s) for the pharmacological activity is unclear, these data suggest that compounds within this series, e.g., N,N-dimethyl-8,8-dipropyl-2-azaspiro[4.5]decane-2-propanamine dihydrochloride, may provide effective therapy in diseases of autoimmune origin and/or the prevention of rejection in tissue transplantation.

Spiro[4,5] and spiro[4,6] carboxylic acids: Cyclic analogues of valproic acid. Synthesis and anticonvulsant evaluation

Spiro[4,5]decane-2-carboxylic acid, spiro[4,5]decane-2,2-dicarboxylic acid, spiro[4,6]undecane-2-carboxylic acid (12b), spiro[4,6]undecane-2,2-dicarboxylic acid, and spiro[4,6]undecane-2-acetic acid were synthesized by an improved method and evaluated for anticonvulsant activity. These analogues were synthesized to evaluate the role of the carboxylic acid group as an essential substituent in valproic acid (di-n-propylacetic acid, 1). Carbocyclic spiranes are known to resist metabolic alteration so that any activity elicited by these compounds would be due to the carboxylic acid function and not to any metabolic change. Spiro[4,6]undecane-2-carboxylic acid (12b) was the most active analogue tested and the pentylenetetrazol and picrotoxin evaluations of 12b compared favorably to 1. However, 12b failed to provide adequate protection against maximal electroshock seizures, bicuculline, or strychnine in mice. Possible reasons for these results are discussed.