31930-36-6

Usage

Uses

Used in Chemical Synthesis:
CIS-3-IODOACRYLIC ACID ETHYL ESTER is used as a reactant for the synthesis of complex naphtho(benzo)furans and in the cobalt-catalyzed cross-coupling of functionalized organozinc pivalates. This application is due to its reactivity and ability to form new chemical bonds with other compounds.
Used in Pharmaceutical Industry:
CIS-3-IODOACRYLIC ACID ETHYL ESTER is used as a building block in the synthesis of various pharmaceutical compounds, such as vinyl sulfides, (Z)-1-iodohept-1-en-3-ol, (E)-1-iodohept-1-en-3-ol, (Z)-β-iodoacrolein, and 6-oxo-M1Guo. Its use in this industry is attributed to its versatility in creating diverse molecular structures with potential therapeutic properties.

InChI:InChI=1/C5H7IO2/c1-2-8-5(7)3-4-6/h3-4H,2H2,1H3/b4-3-

Upstream product

• 16205-84-8 ethyl 3-(trimethylsilyl)propynoate 
• 64-17-5 ethanol 
• 6214-35-3 (Z)-3-iodoprop-2-enoic acid 
• 6372-02-7 (E)-3-iodoacrylic acid 
• 623-47-2 propynoic acid ethyl ester 
• 71815-44-6 (E/Z)-3-iodoacrylic acid 

Downstream Products

• 1955-39-1 5-phenyl-3H-furan-2-one 
• 60112-29-0 5-cyclohexyl-5-hydrofuran-2-one 
• 37428-57-2 (Z)-3-iodoprop-2-en-1-ol 
• 189368-12-5 (Z)-5-phenyl 2-penten-4-ynoic acid ethyl ester 
• 165522-44-1 (Z)-1-Iodo-3-phenylprop-1-en-3-ol 
• 266325-19-3 ethyl 6-phenylhex-5-yn-(2Z)-enoate 
• 14251-57-1 1,1-diphenyl-1,2-propadiene 
• 356788-89-1 1,1-dimethylethyl 2(S)-[(1Z)-3-ethoxy-3-oxo-1-propenyl]-1-pyrrolidinecarboxylate 
• 350022-50-3 1,1-dimethylethyl 2(R)-[(1Z)-3-ethoxy-3-oxo-1-propenyl]-1-pyrrolidinecarboxylate 
• 4610-69-9 (Z)-ethyl cinnamate 
• 38447-06-2 ethyl (2Z,4E)-5-phenyl-2,4-pentadienoate 
• 37993-76-3 3-phenylisoquinoline 

Relevant academic research and scientific papers

Synthesis of 2E,4E,6E,11Z-octadecatetraenoic acid of the Rhizobium leguminosarum biovar viciae Nod factor

2E,4E,6E,11Z-Octadecatetraenoic acid was synthesized in a good yield and in a stereospecific manner by coupling a vinylborane compound and ethyl trans-3-iodoacrylate. The trienic system (E,E,E) was obtained by successive use of metal-catalyzed coupling and hydro-metallation reactions.

Synthesis of (+)-crocacin D and simplified bioactive analogues

The total synthesis of (+)-crocacin D has been achieved in 15 steps (9 isolated intermediates) and 14% overall yield from commercially available starting materials and using (+)-crocacin C as a key intermediate. A number of simplified analogues and their biological activities are also reported.

Substituent Effects in the Intramolecular Diels-Alder Reaction of 6-Furylhexenoates

The series of furyl enone esters, 4a-c, were synthesized from furan or furfural by straightforward routes. Their thermal intramolecular Diels-Alder reactions to give the tricyclic ketones 5a-c were studied in acetonitrile and toluene at two temperatures and the kinetics of the reactions determined. A comparison of these data with that obtained for the corresponding esters 2 to give the lactones 3 indicates that the rate enhancements seen for the esters (rate of dimethyl 310 times that of monomethyl) are much larger than those seen for the ketones (rate of dimethyl 6.8 times that of monomethyl). Thus, this is additional evidence for the earlier hypothesis that the presence of the oxygen atom in the tether is a factor responsible for the larger than normal rate enhancements.

Synthesis, radiolabeling, and preliminary in vivo evaluation of [68ga] ipcat-nota as an imaging agent for dopamine transporter

Introduction: Novel radiotracer development for imaging dopamine transporters is a subject of interest because although [99mTc]TRODAT-1, [123I]β-CIT, and [123I]FP-CIT are commercially available;99Mo/99mTc generator is in short supply and123I production is highly dependent on compact cyclotron. Therefore, we designed a novel positron emission tomography (PET) tracer based on a tropane derivative through C-2 modification to conjugate NOTA for chelating68Ga, a radioisotope derived from a68Ge/68Ga generator. Methods: IPCAT-NOTA 22 was synthesized and labeled with [68Ga]GaCl4 ? at room tem-perature. Biological studies on serum stability, LogP, and in vitro autoradiography (binding assay and competitive assay) were performed. Furthermore, ex vivo autoradiography, biodis-tribution, and dynamic PET imaging studies were performed in Sprague Dawley rats. Results: [68Ga]IPCAT-NOTA 24 obtained had a radiochemical yield of ≥90% and a specific activity of 4.25 MBq/nmol. [68Ga]IPCAT-NOTA 24 of 85% radiochemical purity (RCP%) was stable at 37°C for up to 60 minutes in serum with a lipophilicity of 0.88. The specific binding ratio (SBR%) reached 15.8 ± 6.7 at 60 minutes, and the 85% specific uptake could be blocked through co-injection at 100-and 1000-fold of the cold precursor in in vitro binding studies. Tissue regional distribution studies in rats with [68Ga]IPCAT-NOTA 24 showed striatal uptake (0.02% at 5 minutes and 0.007% at 60 minutes) with SBR% of 6%, 25%, and 62% at 5–15, 30–40, and 60–70 minutes, respectively, in NanoPET studies. The RCP% of [68Ga]IPCAT-NOTA 24 at 30 minutes in vivo remained 67.65%. Conclusion: Data described here provide new information on the design of PET probe of conjugate/pendent approach for DAT imaging. Another chelator or another direct method of intracranial injection must be used to prove the relation between [68Ga]IPCAT-NOTA 24 uptake and transporter localization.

Preparation method of selinexor and intermediate thereof

The invention relates to a preparation method of selinexor and an intermediate thereof, which has the advantages of short synthetic route, mild reaction conditions, no foul gas generation in the reaction process, high safety, wide acceptable range of vari

Diastereo- and Enantioselective Cross-Couplings of Secondary Alkylcopper Reagents with 3-Halogeno-Unsaturated Carbonyl Derivatives

Chiral secondary alkylcopper reagents were prepared from the corresponding alkyl iodides with retention of configuration by an I/Li-exchange using tBuLi (?100 °C, 1 min) followed by a transmetalation with CuBr?P(OEt)3 (?100 °C, 20 s). These ste

Total synthesis of selaginpulvilins A and C

An efficient formal total synthesis of two compounds from the selaginpulvilin family of natural products, selaginpulvilin A and C, has been successfully achieved. The tetradehydro Diels-Alder (TDDA) reaction between an enyne and alkyne has been utilized for the creation of the necessary fluorene skeleton. Attempts at the conversion of selaginpulvilin A to selaginpulvilin B, F and H were unsuccessful.

Palladium-catalyzed convenient one-pot synthesis of multi-substituted 2-pyrones via transesterification and alkenylation of enynoates

An efficient one-pot protocol for the synthesis of multi-substituted 2-pyrone derivatives from internal alkynes and unactivated alkenes is reported. The methodology involves difunctionalization of internal alkynes by using Pd(II) as a catalyst alongwith X-Phos as ligand via 6-endo transesterification and subsequent alkenylation pathway. Notable features include simple and easily available starting materials, including a range of unactivated alkenes, reduced synthetic steps and mild reaction conditions with high efficiency.

Intramolecular cascade rearrangements of enynamine derived ketenimines: Access to acyclic and cyclic amidines

Copper-catalyzed reaction of enynamines with sulfonylazides provides acyclic and cyclic amidines. Nucleophilic addition of the tethered amino group on the in situ generated ketenimine forms a six-membered cyclic zwitterionic intermediate which facilitates

Catalyst-Free Synthesis of Borylated Lactones from Esters via Electrophilic Oxyboration

A catalyst-free oxyboration reaction of alkynes is developed. The resulting borylated isocoumarins and 2-pyrones are isolated as boronic acids, pinacolboronate esters, or potassium organotrifluoroborate salts, providing a variety of bench-stable organobor