127172-22-9

Basic information

• Product Name: 1-(3,4-diMethoxyphenyl)-3-(diMethylaMino)prop-2-en-1-one
• Synonyms: 1-(3,4-diMethoxyphenyl)-3-(diMethylaMino)prop-2-en-1-one;1-(3,4-Dimethoxyphenyl)-3-(dimethylamino)-2-propen-1-one;(E)-1-(3,4-dimethoxyphenyl)-3-dimethylamino-prop-2-en-1-one;(E)-1-(3,4-dimethoxyphenyl)-3-dimethylaminoprop-2-en-1-one;6R-0043;MLS000546453;SMR000179851;ZINC01394484
• CAS NO: 127172-22-9
• Molecular Formula: C₁₃H₁₇NO₃
• Molecular Weight: 235.27898
• Mol File: 127172-22-9.mol
• Article Data: 30

Chemical Properties

• Melting Point: 124-125℃
• Boiling Point: 352.9 °C at 760 mmHg
• Flash Point: 167.2 °C
• Appearance: /
• Density: 1.072 g/cm³
• CAS DataBase Reference: 1-(3,4-diMethoxyphenyl)-3-(diMethylaMino)prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,4-diMethoxyphenyl)-3-(diMethylaMino)prop-2-en-1-one(127172-22-9)
• EPA Substance Registry System: 1-(3,4-diMethoxyphenyl)-3-(diMethylaMino)prop-2-en-1-one(127172-22-9)

Safety Data

• Hazardous Substances Data: 127172-22-9(Hazardous Substances Data)

Usage

General Description

1-(3,4-Dimethoxyphenyl)-3-(dimethylamino)prop-2-en-1-one, also known as 3,4-Dimethoxy-α,β-dimethylphenethylamine, is a chemical compound with a complex molecular structure. It is commonly used in scientific research and pharmaceutical development, with potential applications in the fields of medicine and biotechnology. The compound possesses both an alpha, beta-unsaturated ketone and a dimethylamino group, making it a versatile building block for synthesizing a wide range of organic compounds. It also has the potential to exhibit interesting pharmacological properties, potentially serving as a lead compound for the development of new drugs. However, further research and investigation are necessary to fully understand and harness the potential of this complex chemical compound.

Upstream product

• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 78558-43-7 6-(3,4-dimethoxyphenyl)-3-cyano-1,2-dihydro-2-oxopyridine 
• 951907-48-5 2-chloro-6-(3,4-dimethoxyphenyl)nicotinonitrile 
• 951907-76-9 6-(3,4-dimethoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-3-ylamine 
• 1203608-48-3 5-(3,4-dimethoxyphenyl)-1-phenylpyrazole 
• 625370-79-8 6-(3,4-dimethoxyphenyl)-3-cyanopyridine-2-(1H)-thione 
• 1254340-16-3 (3,4-dimethoxy-phenyl)-(5-hydroxy-naphtho[1,2-b]furan-3-yl)-methanone 
• 17249-66-0 (3,4-dimethoxyphenyl)(5-hydroxy-benzofuran-3-yl)methanone 
• 1254339-30-4 (6,7-dibromo-5-hydroxy-benzofuran-3-yl)-(3,4-dimethoxy-phenyl)-methanone 
• 1254339-34-8 (6,7-dichloro-5-hydroxy-benzofuran-3-yl)-(3,4-dimethoxy-phenyl)-methanone 
• 1036272-02-2 (Z)-3-chloro-3-(3,4-dimethoxyphenyl)acrylaldehyde 
• 1254339-36-0 6,7-dichloro-3-(3,4-dimethoxy-benzoyl)-benzofuran-4,5-dione 
• 1254339-32-6 6,7-dibromo-3-(3,4-dimethoxy-benzoyl)-benzofuran-4,5-dione 
• 1254339-58-6 3-(3,4-dimethoxy-benzoyl)-naphtho[1,2-b]furan-4,5-dione 
• 1416314-65-2 (S)-N-((3-(3-fluoro-4-(5-(3,4-dimethoxyphenyl)-1H-pyrazol-1-yl)phenyl)-2-oxooxazolidin-5-yl)methyl) acetamide 

Relevant articles and documents

Novel sulfonamide derivatives carrying a biologically active 3,4-dimethoxyphenyl moiety as VEGFR-2 inhibitors

Novel sulfonamides 3-19 with a biologically active 3,4-dimethoxyphenyl moiety were designed and synthesized. The structures of the synthesized compounds were established using elemental analyses, IR, 1H-NMR, 13C-NMR spectral data and mass spectroscopy. All the synthesized compounds were evaluated for their in vitro anticancer activity against four cancer cell lines, namely human hepatocellular carcinoma (HepG2), human medulloblastoma (Daoy), human cervical cancer (HeLa), and human colon cancer (HT-29), by using a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and dasatinib as the reference drug. Among the tested derivatives, compounds 4, 10, 16, and 19 showed good activity as cytotoxic agents. The most active derivatives were evaluated for their ability to inhibit vascular endothelial growth factor receptor (VEGFR)-2. Compounds Z-4-(3-(3,4-dimethoxyphenyl)-3-oxoprop-1-enylamino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)-benzenesulfonamide 10 and Z-4-(3-(3,4-dimethoxyphenyl)-3-oxoprop-1-enylamino)-N-(1H-indazol-6-yl)-benzenesulfonamide 19 were more active as VEGFR-2 inhibitors than dasatinib. Molecular docking of the most active derivatives on the active site of VEGFR-2 revealed that compound 19 exhibited favorable and promising results.

DDQ-mediated oxidative coupling reaction of N,N-dimethyl enaminones with cycloheptatriene

An efficient 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated oxidative coupling reaction of N,N-dimethyl enaminones with cycloheptatriene is developed. It provides a variety of α-alkenylated 1,3-dicarbonyl compounds in moderate to good yields under mild conditions.

Microscale Parallel Synthesis of Acylated Aminotriazoles Enabling the Development of Factor XIIa and Thrombin Inhibitors

Herein we report a microscale parallel synthetic approach allowing for rapid access to libraries of N-acylated aminotriazoles and screening of their inhibitory activity against factor XIIa (FXIIa) and thrombin, which are targets for antithrombotic drugs. This approach, in combination with post-screening structure optimization, yielded a potent 7 nM inhibitor of FXIIa and a 25 nM thrombin inhibitor; both compounds showed no inhibition of the other tested serine proteases. Selected N-acylated aminotriazoles exhibited anticoagulant properties in vitro influencing the intrinsic blood coagulation pathway, but not extrinsic coagulation. Mechanistic studies of FXIIa inhibition suggested that synthesized N-acylated aminotriazoles are covalent inhibitors of FXIIa. These synthesized compounds may serve as a promising starting point for the development of novel antithrombotic drugs.

Harnessing Stereospecific Z-Enamides through Silver-Free Cp?Rh(III) Catalysis by Using Isoxazoles as Masked Electrophiles

The stereospecific synthesis of Z-enamides is described in this paper. For the first time, isoxazoles have been employed as electrophiles in C-H functionalization to afford thermodynamically less stable Z-enamides utilizing salicylaldehydes in an atom- and step-economic fashion. The stereochemistry of enamides might originate from the relative disposition of atoms present in isoxazole and the intramolecular hydrogen bonding. The reaction showed excellent scope as several structurally and electronically diverse salicylaldehydes and isoxazoles reacted efficiently.