67629-62-3

Usage

Uses

Used in Pesticide Industry:
(E)-Methyl 4-(diethoxyphosphoryl)but-2-enoate is used as a pesticide intermediate for its pesticidal properties, helping to control and manage various pests that can damage crops and affect agricultural productivity.
Used in Organic Synthesis:
As a versatile synthetic intermediate, (E)-Methyl 4-(diethoxyphosphoryl)but-2-enoate is used in the production of various organic compounds. Its unique chemical structure allows for its incorporation into a wide range of molecules, making it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Agricultural Applications:
Given its pesticidal properties and moderate toxicity, (E)-Methyl 4-(diethoxyphosphoryl)but-2-enoate is used in agricultural applications to protect crops from pests and enhance overall crop yield. Its non-bioaccumulative nature in the environment makes it a preferred choice for certain agricultural practices.
Used in Industrial Applications:
(E)-Methyl 4-(diethoxyphosphoryl)but-2-enoate's stability and versatility in organic synthesis make it suitable for various industrial applications, where it can be used to produce a range of products, from pharmaceuticals to specialty chemicals that serve different purposes in the industry.

Upstream product

• 1117-71-1 methyl-4-bromo-2-butenoate 
• 122-52-1 triethyl phosphite 
• 623-43-8 crotonic acid methyl ester 
• 78-40-0 triethyl phosphate 
• 1117-71-1 methyl 4-bromocrotonate 
• 121-45-9 phosphorous acid trimethyl ester 

Downstream Products

• 4807-58-3 methyl 13-desmethyl-retinoate 
• 5507-79-9 methyl 9,13-bisdesmethylretinoate 
• 7328-33-8 methyl (2E,4E)-decadienoate 
• 6190-46-1 methyl (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)penta-2,4-dienoate 
• 101492-92-6 methyl 10-benzyloxy-(2E,4E)-decadienoate 
• 92356-69-9 methyl (2E,4E)-5-(3-nitrophenyl)-2,4-pentadienoate 
• 92356-68-8 (2E,4E)-5-(4-Nitro-phenyl)-penta-2,4-dienoic acid methyl ester 
• 4493-42-9 methyl (2E,4Z)-deca-2,4-dienoate 
• 92356-73-5 5t-(4-dimethylamino-phenyl)-penta-2t,4-dienoic acid methyl ester 
• 32451-97-1 (3E, 5Z)-3,5-dodecadien-1-ol 
• 18485-38-6 (2E,4E)-dodeca-2,4-dien-1-ol 
• 38447-05-1 (2E,4E)-methyl 5-phenylpenta-2,4-dienoate 
• 287717-33-3 (2E,4E)-(S)-7-(tert-Butyl-diphenyl-silanyloxy)-nona-2,4-dien-8-ynoic acid methyl ester 
• 507222-38-0 methyl (2E,4E)-5-(3-bromophenyl)penta-2,4-dienoate 

Relevant academic research and scientific papers

Stereoselective ozonolysis of TMS-substituted allylic alcohol derivatives and synthesis of 14R,15 S - And 14 S,15 S-diHETE

Ozonolysis of TMS-substituted olefins produces α-carbonyl TMS peroxides without cleavage of the CC bond. Herein, stereochemistry in the ozonolysis was studied using silyl derivatives of (E)- and (Z)-(1-TMS)alk-1-en-3-ols. The (E)-isomers afforded the anti-3-siloxy-2-(TMS-oxy)aldehydes as the major stereoisomer (anti/syn = 3-9:1) after reductive work-up with Ph3P. In contrast, Z-olefins selectively gave the syn isomers with syn/anti ratios of 4-19:1. Facial selection was speculated based on the Cieplak effect. This ozonolysis was successfully applied for the synthesis of 14R,15S- and 14S,15S-diHETEs (anti and syn isomers, respectively) in enantioenriched forms.

Asymmetric Total Synthesis of (+)-Coprophilin

In this paper, we report the first total synthesis of (+)-coprophilin, an anticoccidial agent, by constructing the chiral linear precursor via a Mukaiyama-Evans aldol reaction and a stereoselective intramolecular Diels-Alder reaction. The proposed method can be used to provide large amounts of (+)-coprophilin, which exhibits a 3,4,5,6,7-pentasubstituted Δ 1,2 -octalin core structure.

A NIR fluorescent probe for fatty acid amide hydrolase bioimaging and its application in development of inhibitors

Fatty acid amide hydrolase (FAAH) is primarily responsible for the inactivation of fatty acid ethanolamide (FAE) and is involved in a variety of biological functions related to diseases of the nervous system. Herein, we developed a highly selective and sensitive FAAH-activated near-infrared fluorescent probe named DAND and achieved the real-time detection and imaging of FAAH activity in complex biosystems. Moreover, a visual high-throughput screening method was established using DAND, piperine was identified as a novel inhibitor of FAAH. Based on the interaction of piperine with FAAH, a more potent FAAH inhibitor (11f) was designed and synthesized which possessed an IC50 value of 0.65 μM. Furthermore, 11f could attenuate the liposaccharide (LPS)-induced activation of BV2 cells, exhibiting an excellent anti-inflammatory activity. These results indicated that DAND could be used as a promising molecular tool for exploring FAAH activity and for rapidly screening potential FAAH inhibitors. In addition, piperine and its derivatives could serve as potential candidate drugs for the treatment of neurodegenerative diseases in the future.

The development of novel cytochrome P450 2J2 (CYP2J2) inhibitor and the underlying interaction between inhibitor and CYP2J2

Human Cytochrome P450 2J2 (CYP2J2) as an important metabolic enzyme, plays a crucial role in metabolism of polyunsaturated fatty acids (PUFAs). Elevated levels of CYP2J2 have been associated with various types of cancer, and therefore it serves as a potential drug target. Herein, using a high-throughput screening approach based on enzymic activity of CYP2J2, we rapidly and effectively identified a novel natural inhibitor (Piperine, 9a) with IC50 value of 0.44 μM from 108 common herbal medicines. Next, a series of its derivatives were designed and synthesised based on the underlying interactions of Piperine with CYP2J2. As expected, the much stronger inhibitors 9k and 9l were developed and their inhibition activities increased about 10 folds than Piperine with the IC50 values of 40 and 50 nM, respectively. Additionally, the inhibition kinetics illustrated the competitive inhibition types of 9k and 9l towards CYP2J2, and K i were calculated to be 0.11 and 0.074 μM, respectively. Furthermore, the detailed interaction mechanism towards CYP2J2 was explicated by docking and molecular dynamics, and our results revealed the residue Thr114 and Thr 315 of CYP2J2 were the critical sites of action, moreover the spatial distance between the carbon atom of ligand methylene and Fe atom of iron porphyrin coenzyme was the vital interaction factor towards human CYP2J2.

COSMETIC OR PHARMACEUTICAL USE OF AVENANTHRAMIDE L

The present invention relates generally to: the cosmetic or pharmaceutical use of avenanthramide L or an oat extract comprising avenanthramide L; avenanthramide L or an oat extract comprising avenanthramide L as a neurokinin-1 receptor NK1R antagonist; and a method for preparing of preparing avenalumic acid and/or avenanthramide L.

(2E,4E)-5-PHENYL-PENTA-2,4-DIEN-1-ONE DERIVATIVE

The present application relates to a novel pentadienoyl compound and a pharmaceutical composition including the same. The pentadienoyl compound of the present application may be used to prevent or treat fatty liver and fatty liver-related disease by inhibiting lipogenesis and lipid accumulation in cells and activating lipid metabolism. In addition, the pentadienoyl compound of the present application may increase a SIRT1 expression level in cells or SIRT1 activity, and thus may be used to prevent or treat a SIRT1-mediated disease. In addition, the pentadienoyl compound of the present application may reduce a CK2 expression level in cells or CK2 activity, and thus may be used to prevent or treat a CK2-mediated disease.

Total Synthesis of Aetheramide A

The first total synthesis of the highly potent anti-HIV natural product aetheramide A was accomplished in 18 steps from four equally complex building blocks. The synthesis established the unknown configuration at C26 and used a configurationally labile β-ketoester moiety for the self-adjustment of the configuration at a methyl branch. The pivotal macrolactamization was achieved by trapping a thermally generated acylketene which was derived from its corresponding dioxinone.

An effective strategy to develop active cinnamic acid-directed antioxidants based on elongating the conjugated chains

To optimize antioxidant activity and lipophilicity of cinnamic acid derivatives (CAs) including ferulic acid, sinapic acid, 3,4-dimethoxycinnamic acid, and p-hydroxycinnamic acid, four analogs bearing an additional double bond between their aromatic ring and propenoic acid moiety were designed and synthesized based on the conjugated chain elongation strategy. The antioxidant performance of the CAs were investigated by 2,2′-diphenyl-1-picrylhydrazyl (DPPH)-scavenging, ferric reducing/antioxidant power, cyclic voltammetry, DNA strand breakage-inhibiting and anti-haemolysis activity assays. It was found that CAs with elongation of conjugated chains display increased DPPH --scavenging, DNA strand breakage-inhibiting and anti-haemolysis activities as compared to their parent molecules, due to their improved hydrogen atom-donating ability and lipophilicity. Overall, this work highlights an effective strategy to develop potential CA-directed antioxidants by elongating their conjugated chain.

Tethered aminohydroxylation: Synthesis of the β-amino acid of microsclerodermins A and B

The utility of the tethered aminohydroxylation (TA) has been demonstrated by synthesis of the complex β-amino acid residue of microsclerodermins A and B. The TA provided a regio- and stereoselective functionalization of a complex homoallylic alcohol. The route includes late-stage introduction of the aliphatic side chain via a cuprate addition and cross metathesis, a tactic designed to render the synthesis applicable to other microsclerodermins.

A chemoenzymatic asymmetric synthesis of methyl (6S,13R)-6,13-dihydroxytetradeca-(2E,4E,8E)-trienoate, a component of Mycosphaerella rubella

The first asymmetric synthesis of (6S,13R)-6,13-dihydroxytetradeca-(2E,4E,8E)-trienoate has been developed. The key steps of the synthesis were the use of an efficient lipase-catalyzed acylation, a chiral template-driven enantiocontrolled allylation for introducing the stereogenic centers, and a cross-metathesis for controlling the C-8 olefin geometry.