34450-62-9

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL CIS-3-IODOCROTONATE, 97 is used as an intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs and enhance the production of existing ones.
Used in Agrochemical Industry:
In the agrochemical sector, ETHYL CIS-3-IODOCROTONATE, 97 is utilized as a component in the creation of agrochemicals, playing a role in the production of pesticides and other agricultural chemicals to improve crop protection and yield.
Used in Fragrance Industry:
ETHYL CIS-3-IODOCROTONATE, 97 is employed as a building block in the formulation of fragrance compounds, contributing to the creation of unique scents and perfumes.
Used in Organic Synthesis:
As a versatile chemical compound, ETHYL CIS-3-IODOCROTONATE, 97 is used as an intermediate in organic synthesis for the manufacturing of a variety of chemicals, showcasing its broad applicability in the chemical industry.

Upstream product

• 4341-76-8 Ethyl 2-butynoate 
• 64-17-5 ethanol 
• 34450-60-7 (Z)-3-iodobut-2-enoic acid 

Downstream Products

• 21053-63-4 methyl-3 phenyl-4 Δ²⁽³⁾-butyrolactone 
• 23652-67-7 ethyl (Z)-β-acetylaminobut-2-enoate 
• 724422-92-8 (Z)-ethyl 8-(tert-butyldiphenylsilanyloxy)-3,7-dimethyloct-2-enoate 
• 349138-08-5 C₁₃H₁₄ClNO₃ 
• 945-93-7 ethyl (Z)-3-phenylbut-2-enoate 
• 7706-82-3 (Z)-3-(4-methoxyphenyl)-2-butenoic acid ethyl ester 
• 1268686-82-3 5-(4-chlorophenyl)-4-methylfuran-2(5H)-one 

Relevant academic research and scientific papers

Enantioselective Lactonization by π-Acid-Catalyzed Allylic Substitution: A Complement to π-Allylmetal Chemistry

Asymmetric allylic alkylation (AAA) is a powerful method for the formation of highly useful, non-racemic allylic compounds. Here we present a complementary enantioselective process that generates allylic lactones via π-acid catalysis. More specifically, a

Unified Approach to Furan Natural Products via Phosphine-Palladium Catalysis

Polyalkyl furans are widespread in nature, often performing important biological roles. Despite a plethora of methods for the synthesis of tetrasubstituted furans, the construction of tetraalkyl furans remains non-trivial. The prevalence of alkyl groups in bioactive furan natural products, combined with the desirable bioactivities of tetraalkyl furans, calls for a general synthetic protocol for polyalkyl furans. This paper describes a Michael–Heck approach, using sequential phosphine-palladium catalysis, for the preparation of various polyalkyl furans from readily available precursors. The versatility of this method is illustrated by the total syntheses of nine distinct polyalkylated furan natural products belonging to different classes, namely the furanoterpenes rosefuran, sesquirosefuran, and mikanifuran; the marine natural products plakorsins A, B, and D and plakorsin D methyl ester; and the furan fatty acids 3D5 and hydromumiamicin.

Kinetic Resolution and Dynamic Kinetic Resolution of γ-Aryl-Substituted Butenolides via Copper-Catalyzed 1,4-Hydroboration

Kinetic resolution (KR) and dynamic kinetic resolution (DKR) of γ-aryl and heteroaryl-substituted butenolides via CuH-catalyzed 1,4-hydroboration using pinacolborane is reported. With a copper-Ph-BPE catalyst, selectivity factors were extremely high (s=>400) with regard to the kinetic resolution of β-methyl-γ-phenyl butenolide; DKR was possible in the presence of an amine base (DBU), which facilitated racemization of the starting unsaturated lactones. The reaction provided easy access to highly enantioenriched γ-butyrolactones (>99% ee) containing β,γ-substituents. (Figure presented.).

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

Metal-Free Transfer Hydroiodination of C-C Multiple Bonds

The design and a gram-scale synthesis of a bench-stable cyclohexa-1,4-diene-based surrogate of gaseous hydrogen iodide are described. By initiation with a moderately strong Br?nsted acid, hydrogen iodide is transferred from the surrogate onto C-C multiple bonds such as alkynes and allenes without the involvement of free hydrogen iodide. The surrogate fragments into toluene and ethylene, easy-to-remove volatile waste. This hydroiodination reaction avoids precarious handling of hydrogen iodide or hydroiodic acid. By this, a broad range of previously unknown or difficult-to-prepare vinyl iodides can be accessed in stereocontrolled fashion.

Potent Analogues of Abscisic Acid – Identifying Cyano-Cyclopropyl Moieties as Promising Replacements for the Cyclohexenone Headgroup

Synthetic analogues of plant hormone abscisic acid (ABA) bearing a yet unexplored head group motif were prepared based on a combination of agrochemical experience, in vivo hits and structure-based design. It could thus be explored how modifying key parts of ABA's cyclohexenone unit influenced receptor affinity and in vivo efficacy against drought stress in selected crops. Cyano-cyclopropyl groups proved to be suitable replacements of the cyclohexanone moiety leading to ABA analogues with strong activity in vitro and in vivo. Their efficient and versatile synthesis proceeded via Stille or Sonogashira couplings as the key steps. Combining novel cyano-cyclopropyl headgroups with previously identified substituents in the terpenoid side chain afforded the most promising effects against drought stress in crops, particularly canola and wheat.

Nickel-Catalyzed Reductive Allylation of Tertiary Alkyl Halides with Allylic Carbonates

The construction of all C(sp3) quaternary centers has been successfully achieved under Ni-catalyzed cross-electrophile coupling of allylic carbonates with unactivated tertiary alkyl halides. For allylic carbonates bearing C1 or C3 substituents, the reaction affords excellent regioselectivity through the addition of alkyl groups to the unsubstituted allylic carbon terminus. The allylic alkylation method also exhibits excellent functional-group compatibility, and delivers the products with high E selectivity.

SUBSTITUTED CYANO CYCLOALKYL PENTA-2,4-DIENES, CYANO CYCLOALKYL PENT-2-EN-4-YNES, CYANO HETEROCYCLYL PENTA-2,4-DIENES AND CYANO HETEROCYCLYL PENT-2-EN-4-YNES AS ACTIVE SUBSTANCES

The invention relates to cyano cycloalkyl penta-2,4-dienes, cyano cycloalkyl pent-2-en-4-ynes, cyano heterocyclyl penta-2,4-dienes and cyano heterocyclyl pent-2-en-4-ynes of general formula (I), or the salts thereof, where [X-Y], Q, R1, R2, A1, A2, V, W, m and n have the definitions specified in the description. The invention also relates to a production method for same and to the use of same for increasing stress tolerance in plants against abiotic stress, and/or for increasing the plant yield.

Fully substituted pyranones via quasi-heterogeneous genuinely ligand-free migita-stille coupling of iodoacrylates

Migita-Stille coupling of (Z)-?2-iodoacrylates with (E)-?±-stannyl allylic alcohols to furnish 5-alkylidene-4-substituted-5,6-dihydro-2H-pyran-2-ones is efficiently catalyzed by 2% Pd black in DMF, while Pd(PPh3)4 is inactive. Heterogeneous Pd released in solution is most likely responsible for the catalysis. The reaction is applicable to other substrates, without having to resort to ligands, additives, and/or solid support for Pd. The resulting pyranones can be rearranged to fully functionalized pyranones in another single step.

Enantioselective synthesis of all-carbon quaternary stereogenic centers via copper-catalyzed asymmetric allylic alkylation of (Z)-allyl bromides with organolithium reagents

A copper/phosphoramidite catalyzed asymmetric allylic alkylation of Z trisubstituted allyl bromides with organolithium reagents is reported. The reaction affords all-carbon quaternary stereogenic centers in high yields and very good regio- and enantiosele