2769-90-6

Basic information

• Product Name: 3-(1-METHYL-1H-PYRROL-2-YL)-ACRYLIC ACID ETHYL ESTER
• Synonyms: 3-(1-METHYL-1H-PYRROL-2-YL)-ACRYLIC ACID ETHYL ESTER;(2E)-3-(1-Methyl-1H-pyrrol-2-yl)-2-Propenoic acid ethyl ester;(E)-ethyl 3-(1-methyl-1H-pyrrol-2-yl)acrylate
• CAS NO: 2769-90-6
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179.21572
• Mol File: 2769-90-6.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 286.7°C at 760 mmHg
• Flash Point: 127.2°C
• Appearance: /
• Density: 1g/cm³
• Vapor Pressure: 0.0026mmHg at 25°C
• Refractive Index: 1.495
• PKA: -3.97±0.70(Predicted)
• CAS DataBase Reference: 3-(1-METHYL-1H-PYRROL-2-YL)-ACRYLIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(1-METHYL-1H-PYRROL-2-YL)-ACRYLIC ACID ETHYL ESTER(2769-90-6)
• EPA Substance Registry System: 3-(1-METHYL-1H-PYRROL-2-YL)-ACRYLIC ACID ETHYL ESTER(2769-90-6)

Safety Data

• Hazardous Substances Data: 2769-90-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H13NO2/c1-3-13-10(12)7-6-9-5-4-8-11(9)2/h4-8H,3H2,1-2H3/b7-6+

Upstream product

• 96-54-8 N-Methylpyrrole 
• 140-88-5 ethyl acrylate 
• 1192-58-1 N-methylpyrrole aldehyde 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 56454-26-3 1-methyl-2-pyrrolyl chloride 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 

Downstream Products

• 667871-17-2 3-[1-methyl-4-(1-phenyl-cyclopropanecarbonyl)-1H-pyrrol-2-yl]-acrylic acid ethyl ester 
• 667871-12-7 ethyl 3-[1-methyl-4-(4-phenylbutyryl)-1H-pyrrol-2-yl]-2-propenoate 
• 667871-11-6 3-[1-methyl-4-(3-phenyl-propionyl)-1H-pyrrol-2-yl]-acrylic acid ethyl ester 
• 667871-19-4 3-[1-methyl-4-(2-phenyl-cyclopropanecarbonyl)-1H-pyrrol-2-yl]-acrylic acid ethyl ester 
• 667871-14-9 3-[1-methyl-4-(6-phenyl-hexanoyl)-1H-pyrrol-2-yl]-acrylic acid ethyl ester 
• 667871-13-8 3-[1-methyl-4-(5-phenyl-pentanoyl)-1H-pyrrol-2-yl]-acrylic acid ethyl ester 
• 667871-15-0 3-[1-methyl-4-(7-phenyl-heptanoyl)-1H-pyrrol-2-yl]-acrylic acid ethyl ester 
• 667871-16-1 3-[1-methyl-4-(8-phenyl-octanoyl)-1H-pyrrol-2-yl]-acrylic acid ethyl ester 
• 852475-26-4 (2E)-3-[5-[(1E)-3-(3-fluorophenyl)-3-oxo-1-propen-1-yl]-1-methyl-1H-pyrrol-2-yl]-N-hydroxy-2-propenamide 
• 615252-69-2 3-[1-methyl-4-(3-oxo-3-o-tolyl-propenyl)-1H-pyrrol-2-yl]-acrylic acid 
• 615252-67-0 (E)-3-{4-[(E)-3-(3-Chloro-phenyl)-3-oxo-propenyl]-1-methyl-1H-pyrrol-2-yl}-acrylic acid 
• 615252-71-6 3-[1-methyl-4-(3-oxo-3-p-tolyl-propenyl)-1H-pyrrol-2-yl]-acrylic acid 
• 615252-68-1 3-[4-(3-(4-chloro)phenyl-3-oxo-1-propen-1-yl)-1-methyl-1H-pyrrol-2-yl]-2-propenoic acid 
• 615252-70-5 3-[1-methyl-4-(3-oxo-3-m-tolyl-propenyl)-1H-pyrrol-2-yl]-acrylic acid 

Relevant articles and documents

MC - 1568 Synthesis method

The invention provides a synthesis method of MC-1568. The preparation method comprises the steps as follows: step 1, tetrahydrofuran, triethyl phosphonoacetate and potassium tert-butoxide are stirredat the room temperature, a suspension of N-methylpyrrole-2-formaldehyde and tetrahydrofuran is added, the reaction solution is stirred, water is added after the reaction, ethyl acetate is added, the mixed solution is stirred and left to stand for layering, a water layer is extracted with ethyl acetate, and an organic phase is distilled under pressure; step 2, (E)-3-(5-formyl-1-methyl-1H-pyrrole-2-yl)ethyl acrylate is synthesized; step 3, a compound 5 is synthesized; step 4, a compound 6 is synthesized; step 5, MC-1568 is synthesized. By means of the synthesis method, purification in traditional technologies is avoided, and industrialization can be realized.

NOVEL MACROCYCLIC DERIVATIVES, PROCESS FOR PREPARING SAME AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME

Compound of formula (I): wherein A1, A2, Ra, Rb, Rc, Rd, R3, R4, X, Y and G are as defined in the description, and their use in the manufacture of medicaments.

Bioactivity and structure–activity relationship of cinnamic acid derivatives and its heteroaromatic ring analogues as potential high-efficient acaricides against Psoroptes cuniculi

A series of cinnamic acid derivatives and its heteroaromatic ring analogues were synthesized and evaluated for acaricidal activity in vitro against Psoroptes cuniculi, a mange mite. Among them, eight compounds showed the higher activity with median lethal concentrations (LC50) of 0.36–1.07 mM (60.4–192.1 μg/mL) and great potential for the development of novel acaricidal agent. Compound 40 showed both the lowest LC50 value of 0.36 mM (60.4 μg/mL) and the smallest median lethal time (LT50) of 2.6 h at 4.5 mM, comparable with ivermectin [LC50 = 0.28 mM (247.4 μg/mL), LT50 = 8.9 h], an acaricidal drug standard. SAR analysis showed that the carbonyl group is crucial for the activity. The type and chain length of the alkoxy in the ester moiety and the steric hindrance near the ester group significantly influence the activity. The esters were more active than the corresponding thiol esters, amides, ketones or acids. Replacement of the phenyl group of cinnamic esters with α-pyridyl or α-furanyl significantly increase the activity. Thus, a series of cinnamic esters and its heteroaromatic ring analogues with excellent acaricidal activity emerged.