18133-46-5

Basic information

• Product Name: α-(3,4-dimethoxyphenyl)acetoacetonitrile
• CAS NO: 18133-46-5
• Molecular Weight: 219.24
• Mol File: 18133-46-5.mol

Chemical Properties

• CAS DataBase Reference: α-(3,4-dimethoxyphenyl)acetoacetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: α-(3,4-dimethoxyphenyl)acetoacetonitrile(18133-46-5)
• EPA Substance Registry System: α-(3,4-dimethoxyphenyl)acetoacetonitrile(18133-46-5)

Safety Data

• Hazardous Substances Data: 18133-46-5(Hazardous Substances Data)

Upstream product

• 93-17-4 3,4-dimethoxyphenylacetonitrile 
• 141-78-6 ethyl acetate 
• 2466-76-4 N-Acetylimidazole 

Downstream Products

• 1331858-82-2 C₁₅H₁₉NO₃ 
• 156896-96-7 γ-Cyano-γ-3,4-dimethoxyphenyl-γ-isopropyl-1-buten 
• 132576-21-7 5-amino-4-(3,4-dimethoxyphenyl)-3-methyl-1-phenyl-1H-pyrazole 
• 1369597-15-8 1-(3,4-dimethoxyphenyl)-5,6-dimethoxy-2-methyl-1H-indene-1,3-dicarbonitrile 

Relevant articles and documents

Stereoselective C?C Oxidative Coupling Reactions Photocatalyzed by Zwitterionic Ligand Capped CsPbBr3 Perovskite Quantum Dots

Semiconductor quantum dots (QDs) have attracted tremendous attention in the field of photocatalysis, owing to their superior optoelectronic properties for photocatalytic reactions, including high absorption coefficients and long photogenerated carrier lifetimes. Herein, by choosing 2-(3,4-dimethoxyphenyl)-3-oxobutanenitrile as a model substrate, we demonstrate that the stereoselective (>99 %) C?C oxidative coupling reaction can be realized with a high product yield (99 %) using zwitterionic ligand capped CsPbBr3 perovskite QDs under visible light illumination. The reaction can be generalized to different starting materials with various substituents on the phenyl ring and varied functional moieties, producing stereoselective dl-isomers. A radical mediated reaction pathway has been proposed. Our study provides a new way of stereoselective C?C oxidative coupling via a photocatalytic means using specially designed perovskite QDs.

PYRAZOLO[1,5-A]PYRIMIDINES AS ANTIVIRAL COMPOUNDS

A compound of formula (I) or a pharmaceutically acceptable salt thereof, useful in therapy, in particular in the treatment of a viral infection.

PYRAZOLO[1,5-A]TRIAZIN-4-AMINE DERIVATIVES USEFUL IN THERAPY

A compound of formula (I), or a pharmaceutically acceptable salt thereof, useful in therapy, in particular in the treatment of a viral infection.

Phenoxide leaving group SNAr strategy for the facile preparation of 7-amino-3-aryl pyrazolo[1,5-a]pyrimidines from a 3-bromo-7-phenoxypyrazolo[1,5-a]pyrimidine intermediate

We have discovered a 3-bromo-7-phenoxypyrazolo[1,5-a]pyrimidine intermediate that allows for the direct sequential funtionalization of the 3-position and 7-position of a pyrazolo[1,5-a]pyrimidine scaffold. The intermediate and general method described herein offer an improvement over prior methods, particularly in cases where multiple unique 3-aryl substituents are to be incorporated in conjunction with multiple unique 7-amino substituents.

Deacylative allylation: Allylic alkylation via retro-Claisen activation

A new method for allylic alkylation of a variety of relatively nonstabilized carbon nucleophiles is described herein. In this process of "deacylative allylation", the coupling partners, an allylic alcohol and a ketone pronucleophile, undergo in situ retro-Claisen activation to generate an allylic acetate and a carbanion. In the presence of palladium, these reactive intermediates undergo catalytic coupling to form a new C-C bond. In comparison to unimolecular decarboxylative allylation, a commonly utilized method for allylation of carbon anions, deacylative allylation is an intermolecular process. Moreover, deacylative allylation allows the direct coupling of readily available allylic alcohols. Lastly, the full utility of deacylative allylation is demonstrated by the rapid construction of a variety 1,6-heptadienes via 3-component couplings.

Oxidative aromatic C-O bond formation: synthesis of 3-functionalized benzo[b]furans by FeCl3-mediated ring closure of a-Aryl ketones

A variety of 3-functionalized benzo[b]furans were achieved by way of a FeCl3-medlated Intramolecular cyclization of electron-rich a-aryl ketones. The alkoxy substituent on the benzene ring In the substrates was essential for an efficient cyclization to occur. This novel method allows the construction of benzo[b]furan rings by joining the O-atom on the side chain to the benzene ring via direct oxidative aromatic C-O bond formation.

Synthesis of N-substituted indole derivatives via PIFA-mediated intramolecular cyclization

(Chemical Equation Presented) A variety of N-arylated and N-alkylated indole derivatives were synthesized by way of a phenyliodine bis(trifluoroacetate) (PIFA)-mediated intramolecular cyclization. This novel method allows for the construction of an indole skeleton by joining the N-atom on the side chain to the benzene ring at the last synthetic step. Other novel pyrrole-fused aromatic compounds can also be achieved by this method.

ANAPLASTIC LYMPHOMA KINASE MODULATORS AND METHODS OF USE

The present invention comprises compounds and pharmaceutical compositions comprising the compounds that are inhibitors of ALK. The invention also comprises methods of using the compounds and compositions to treat diseases mediated by ALK, including diseases such as cancer, immunological disorders, cardiovascular diseases, and other degenerative disorders.

Optimization of 3-phenylpyrazolo[1,5-a]pyrimidines as potent corticotropin-releasing factor-1 antagonists with adequate lipophilicity and water solubility

In our efforts to identify potent CRF1 antagonists with proper physicochemical properties, a series of 3-phenylpyrazolo[1,5-a]pyrimidines bearing polar groups, such as amino, hydroxyl, methoxy, sulfoxide, were designed and synthesized. Several positions of the core structure were identified, where a polar group was tolerated with slight reduction in receptor binding. NBI 30545 (18n) was found to have good binding affinity and potent antagonistic activity at the human CRF1 receptor. Moreover, this compound had proper lipophilicity (logD=2.78) and good solubility in water (>10mg/mL), and exhibited good plasma and brain exposure when given orally.