699-23-0

Usage

Uses

Used in Pharmaceutical Synthesis:
cis-ethyl (1R,2S)-2-cyanocyclopropane-1-carboxylate is used as an intermediate in the synthesis of various pharmaceutical compounds, particularly those with potential antiviral and antibacterial properties. Its unique structure and stereochemistry make it a valuable component in the development of new drugs.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, cis-ethyl (1R,2S)-2-cyanocyclopropane-1-carboxylate is utilized for its potential to contribute to the discovery and design of novel therapeutic agents. Its specific configuration and functional groups can be leveraged to create molecules with desired biological activities and selectivity.
Used in Drug Development:
cis-ethyl (1R,2S)-2-cyanocyclopropane-1-carboxylate plays a role in drug development by serving as a building block for the creation of new pharmaceutical entities. Its incorporation into drug candidates can lead to the discovery of more effective treatments for various diseases, including viral and bacterial infections.

Upstream product

• 100-42-5 styrene 
• 107-13-1 acrylonitrile 
• 7380-81-6 ethyl (dimethylsulfuranylidene)acetate 
• 623-73-4 diazoacetic acid ethyl ester 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 1008789-32-9 4-cyano-4-(diethoxyphosphoryloxy)butyric acid ethyl ester 
• 57519-80-9 (2-cyano-vinyl)-triphenyl-phosphonium; bromide 
• 82272-28-4 cyanomethylenetrimethylammonium iodide 
• 140-88-5 ethyl acrylate 

Downstream Products

• 39891-82-2 (1R,2R)-2-cyanocyclopropane-1-carboxylic acid 
• 30491-95-3 racemic trans-2-(hydroxymethyl)cyclopropanecarbonitrile 
• 45467-35-4 trans-(2-(aminomethyl)cyclopropyl)methanol 

Relevant academic research and scientific papers

AMINOPYRIMIDINYL COMPOUNDS

A compound having the structure: or a pharmaceutically acceptable salt thereof, wherein X is N or CR, where R is hydrogen, deuterium, C1-C4 alkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, aryl, heteroaryl, aryl(C1-C6 alkyl), CN, amino, alkylamino, dialkylamino, CF3, or hydroxyl; A is selected from the group consisting of a bond, C═O, —SO2—, —(C═O)NR0—, and —(CRaRb)q—, where R0 is H or C1-C4 alkyl, and Ra and Rb are independently hydrogen, deuterium, C1-C6 alkyl, C3-C6 cycloalkyl, aryl, aryl(C1-C6 alkyl), heteroaryl, (C1-C6 alkyl)heteroaryl, etc.; A′ is selected from the group consisting of a bond, C═O, —SO2—, —(C═O)NR0′, —NR0′(C═O)—, and —(CRa′Rb′)q—, where R0′ is H or C1-C4 alkyl, and Ra′ and Rb′ are independently hydrogen, deuterium, C1-C6 alkyl, C3-C6 cycloalkyl, aryl, aryl(C1-C6 alkyl), heteroaryl, (C1-C6 alkyl)heteroaryl, heteroaryl(C1-C6 alkyl), and heterocyclic(C1-C6 alkyl); Z is —(CH2)h— or a bond, where one or more methylene units are optionally substituted by one or more C1-C3 alkyl, CN, OH, methoxy, or halo, and where said alkyl may be substituted by one or more fluorine atoms; R1 and R1′ are independently selected from the group consisting of hydrogen, deuterium, C1-C4 alkyl, C3-C6 cycloalkyl, aryl, heteroaryl, aryl(C1-C6 alkyl), CN, etc., wherein said alkyl, aryl, cycloalkyl, heterocyclic, or heteroaryl is further optionally substituted with one or more substituents selected from the group consisting of C1-C6 alkyl, halo, CN, C1-C4 alkylamino, C3-C6 cycloalkyl, etc.; R2 is selected from the group consisting of hydrogen, deuterium, C1-C6 alkyl, C3-C6 cycloalkyl, halo, and cyano, where said alkyl may be substituted by one or more fluorine atoms; R3 is selected from the group consisting of hydrogen, deuterium, and amino; R4 is monocyclic or bicyclic aryl or monocyclic or bicyclic heteroaryl wherein said aryl or heteroaryl is optionally substituted with one or more substituents selected from the group consisting of C1-C6 alkyl, heterocycloalkyl, halo, C3-C6 cycloalkyl, etc., where said alkyl, cycloalkyl, alkoxy, or heterocycloalkyl may be substituted by one or more C1-C6 alkyl, halo, CN, OH, alkoxy, amino, —CO2H, —(CO)NH2, —(CO)NH(C1-C6 alkyl), or —(CO)N(C1-C6 alkyl)2, and where said alkyl may be further substituted by one or more fluorine atoms; R5 is independently selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 alkoxy, and hydroxyl; h is 1, 2 or 3; j and k are independently 0, 1, 2, or 3; m and n are independently 0, 1 or 2; and, q is 0, 1 or 2. Also provided are methods of treatment as Janus Kinase inhibitors and pharmaceutical compositions containing the compounds of the invention and combinations with other therapeutic agents.

ASYMMETRIC CYCLOPROPANATION OF ELECTRON-DEFICIENT OLEFINS WITH DIAZO REAGENTS

Cobalt-catalyzed asymmetric cyclopropanation of electron-deficient olefins.

A general stereoselective method for the synthesis of cyclopropanecarboxylates. A new version of the homologous Horner-Wadsworth- Emmons reaction

The synthesis of α-, β- and γ-substituted α-phosphono-γ-lactones was accomplished using different ring closure and ring homologation strategies. It was found that the lactones could be selectively transformed into the corresponding ethyl cyclopropanecarboxylates by treatment with sodium ethoxide in boiling THF. The reported reaction provides an attractive alternative to the classical homologous Horner-Wadsworth-Emmons approach to the construction of cyclopropanes with electron-withdrawing functionalities. This journal is The Royal Society of Chemistry.

Cobalt-catalyzed asymmetric cyclopropanation of electron-deficient olefins

The cobalt(II) complex of a D2-symmetric chiral porphyrin [Co(1)] is an effective catalyst for asymmetric cyclopropanation of electron-deficient olefins, including α,β-unsaturated esters, amides, ketones, and nitriles. Due to the absence of dimerization of diazo compounds, the catalytic reactions can be performed in one-pot protocol using olefins as the limiting reagent, forming the desired electrophilic cyclopropane derivatives in high yields and selectivities under mild conditions. In most cases, both excellent diastereo- and enantioselectivity were achieved. Copyright

Preparation of new functionalized cyclopropylmagnesium reagents

An I-Mg or Br-Mg exchange reaction has enabled ester-functionalized cyclopropylmagnesium derivatives including magnesium carbenoids to be prepared for the first time in high yield. These magnesium reagents are configurationally stable and react stereosele

An efficient and highly enantio- and diastereoselective cyclopropanation of olefins catalyzed by Schiff-base ruthenium(II) complexes

Both electron-rich and electron-deficient olefins - such as styrene and methyl methacrylate - undergo efficient (yields > 90%) cyclopropanation with ethyl diazoacetate as the carbene source to give predominantly trans products with exceptionally high enantioselectivity when the (salen)Ru catalyst shown is used (see scheme).

Synthesis and antiherpetic activity of (±)-9-[[(Z)-2-(hydroxymethyl)cyclopropyl]methyl]guanine and related compounds

A series of analogues of acyclovir and ganciclovir were prepared in which conformational constrainst were imposed by incorporation of a cyclopropane ring or unsaturation into the side chain. In addition, several related base-modified compounds were synthesized. These acyclonucleosides were evaluated for enzymatic phosphorylation and DNA polymerase inhibition in a staggered assay and for inhibitory activity against herpes simplex virus types 1 and 2 in vitro. Certain of the guanine or 8-azaguanine derivatives were good substrates for the viral thymidine kinase and were further converted to triphosphate, but none was a potent inhibitor of the viral DNA polymerase. Nevertheless, one member of this group, (±)-9-[[(Z)-2-(hydroxymethyl)cyclopropyl]methyl]guanine (3a), displayed significant antiherpetic activity in vitro, superior to that of the corresponding cis olefin 4a. Another group, typified by (±)-9-[[(E)-2-(hydroxymethyl)cyclopropyl]methyl]adenine (17b), possessed modest antiviral activity despite an apparent inability to be enzymatically phosphorylated. The relationship of side-chain conformation and flexibility to biological activity in this series is discussed.

Cyclopropanation of α,β-Unsaturated Carbonyl Compounds and Nitriles with Diazo Compounds. The nature of the Involvement of Transition-Metal Promoters

In the presence of molybdenum hexacarbonyl or molybdenum(II) acetate, ethyl diazoacetate and α-diazoacetophenone react with α,β-unsaturated carbonyl compounds and nitriles to form derivative cyclopropane and vinyl CH insertion products.In the absence of these promoters or in the presence of catalytic amounts of pyridine, 2-pyrazolines are the major or sole reaction products.Kinetic investigations for reactions between ethyl diazoacetate and α,β-unsaturated esters and nitriles in the presence of Mo(CO)6, Mo2(OAc)4, or pyridine demonstrate the absence of any significant influence by these molybdenum promoters or pyridine on the rates and activation parameters for ethyl diazoacetate decomposition.Representative 1-pyrazolines have been synthesized and observed to undergo dinitrogen extrusion without apparent influence by molybdenum promoters.The composite results suggest that these molybdenum promoted reactions occur by dipolar cycloaddition of diazocarbonyl compounds to α,β-unsaturated systems and that the derivative 1-pyrazoline intermediates undergo dinitrogen extrusion to form the observed cyclopropane and vinyl CH insertion products.Molybdenum promoters function to inhibit competitive tautomerization of the initially formed cycloaddition products.The relative effectiveness of a broad selection of transition-metal compounds in directing reactions between ethyl diazoacetate and α,β-unsaturated esters and nitriles to cyclopropane products is described.The cycloaddition / dinitrogen extrusion pathway is presented as a viable mechanism for cyclopropanation of α,β-unsaturated systems by diazo compounds, even for reactions performed in the presence of traditional cyclopropanation catalysts.