27347-13-3

Basic information

• Product Name: 4-(2-methoxyphenyl)morpholine
• Synonyms: 4-(2-methoxyphenyl)morpholine
• CAS NO: 27347-13-3
• Molecular Formula: C₁₁H₁₅NO₂
• Molecular Weight: 193.2423
• Mol File: 27347-13-3.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-(2-methoxyphenyl)morpholine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-methoxyphenyl)morpholine(27347-13-3)
• EPA Substance Registry System: 4-(2-methoxyphenyl)morpholine(27347-13-3)

Safety Data

• Hazardous Substances Data: 27347-13-3(Hazardous Substances Data)

Upstream product

• 90-04-0 2-methoxy-phenylamine 
• 111-46-6 diethylene glycol 
• 110-91-8 morpholine 
• 529-28-2 4-iodoanisol 
• 321-28-8 1-fluoro-2-methoxybenzene 
• 4394-85-8 4-morpholinecarboxaldehyde 
• 766-51-8 2-Chloroanisole 
• 111-44-4 3-oxa-1,5-dichloropentane 
• 4416-67-5 2-tosyloxyanisole 
• 5765-65-1 4-(benzoyloxy)morpholine 
• 79422-01-8 tris(2-methoxyphenyl)-1,3,5,2,4,6-trioxatriborinane 
• 85630-19-9 N,N-diethyl-1-carbamyloxy-2-methoxybenzene 
• 1137-57-1 2-methoxyphenyl N,N-dimethylsulfamate 
• 578-57-4 2-bromoanisole 

Downstream Products

• 1607827-24-6 4-[2-(prop-2-en-1-yloxy)phenyl]morpholine 
• 1616075-15-0 N-(3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)-2-(2-morpholinophenoxy)acetamide 
• 1616077-58-7 ethyl 2-(2-morpholinophenoxy)acetate 
• 41536-44-1 2-(4-morpholinyl)-phenol 
• 68659-83-6 4-(6-methoxy-cyclohexa-1,3-dienyl)-morpholine 

Relevant articles and documents

Aerobic iron-catalyzed site-selective C(sp3)–C(sp3) bond cleavage in N-heterocycles

The kinetic and thermodynamic stability of C(sp3)–C(sp3) bonds makes the site-selective activation of these motifs a real synthetic challenge. In view of this, herein a site-selective method of C(sp3)–C(sp3) bon

N-substituted aminobiphenyl palladacycles stabilized by dialkylterphenyl phosphanes: Preparation and applications in C[sbnd]N cross-coupling reactions

Neutral and cationic N-methyl- and N-phenyl-2-aminobiphenyl methanesulfonate palladacycles stabilized with dialkylterphenyl phosphanes have been prepared and characterized. Neutral structures are favored with the less bulky phosphane PMe2ArXyl2, L1, while more sterically demanding ligands PiPr2ArXyl2, L3, and PCyp2ArXyl2 (Cyp = cyclopentyl), L4, lead to cationic complexes in which the phosphane exhibits a bidentate κ1-P, η1-Carene coordination mode involving one of the ipso carbon atoms of a flanking terphenyl aryl ring. The complexes were evaluated for activity in C[sbnd]N cross-coupling reactions and [Pd(N-methyl-2-aminobiphenyl)L4](OMs) (OMs = mesylate) was identified as the most efficient precatalyst, facilitating the coupling of aryl chlorides with secondary and primary amines and indoles.

NOVEL HETEROCYCLIC COMPOUNDS AS CDK8/19 INHIBITORS

The present invention relates to novel compounds of formula (I): or a pharmaceutically acceptable salt or stereoisomer thereof, which exhibit the properties of a CDK 8/19 inhibitor. The invention also relates to a pharmaceutical composition containing said compounds and to the use thereof as pharmaceutical drugs for treating diseases or disorders.

Ru(II)-Catalyzed Amination of Aryl Fluorides via η6-Coordination

We developed a Ru/hemilabile-ligand-catalyzed nucleophilic aromatic substitution (SNAr) of aryl fluorides as the limiting reagents. Significant ligand enhancement was demonstrated by the engagement of both electron-rich and neutral arenes in the SNAr amination without using excess arenes. Preliminary mechanistic studies revealed that the nucleophilic substitution proceeds on a η6-complex of the Ru catalyst and the substrate, and the hemilabile ligand facilitates dissociation of products from the metal center.

Transition-Metal-Catalyzed Amination of Aryl Fluorides

Arene activation via transition-metal (TM) η 6-coordination has merged as a powerful method to diversify the aromatic C-F bond, which is relatively less reactive due to its high bond energy. However, this strategy in general requires to use largely excess arenes or TM η 6-complexes as the substrates. Herein, we highlight our recent work on the catalytic S NAr amination of electron-rich and electron-neutral aryl fluorides that are inert in classical S NAr reactions. This protocol enabled by a Ru/hemilabile ligand catalyst covers a broad scope of substrates without wasting arenes. Mechanistic studies revealed that the nucleo?-philic substitution proceeded on a Ru η 6-arene complex, and the hemilabile ligand significant promoted the arene dissociation.

Dialkylterphenyl Phosphine-Based Palladium Precatalysts for Efficient Aryl Amination of N-Nucleophiles

A series of 2-aminobiphenyl palladacycles supported by dialkylterphenyl phosphines, PR2Ar′ (R=Me, Et, iPr, Cyp (cyclopentyl), Ar′=ArDipp2, ArXyl2f, Dipp (2,6-C6H3-(2,6-C6H3-(CHMe2)2)2), Xyl=xylyl) have been prepared and structurally characterized. Neutral palladacycles were obtained with less bulky terphenyl phosphines (i.e., Me and Et substituents) whereas the largest phosphines provided cationic palladacycles in which the phosphines adopted a bidentate hemilabile k1-P,η1-Carene coordination mode. The influence of the ligand structure on the catalytic performance of these Pd precatalysts was evaluated in aryl amination reactions. Cationic complexes bearing the phosphines PiPr2ArXyl2 and PCyp2ArXyl2 were the most active of the series. These precatalysts have demonstrated a high versatility and efficiency in the coupling of a variety of nitrogen nucleophiles, including secondary amines, alkyl amines, anilines, and indoles, with electronically deactivated and ortho-substituted aryl chlorides at low catalyst loadings (0.25–0.75 mol % Pd) and without excess ligand.

Aryl-Diadamantyl Phosphine Ligands in Palladium-Catalyzed Cross-Coupling Reactions: Synthesis, Structural Analysis, and Application

Synthesis, temperature-dependent NMR structure investigation and utilization of a new, stable and easily accessible aryl-diadamantylphosphine ligand family is reported. The bulky and electron-rich phosphorus center of the ligand enhances the catalytic activity of palladium in cross-coupling reactions of sterically demanding ortho-substituted aryl halides. In our study, we demonstrated the synthetic applicability of the new phosphine ligands in Buchwald-Hartwig and tosyl hydrazone coupling reactions.

Methyl-α-d-glucopyranoside as Green Ligand for Selective Copper-Catalyzed N-Arylation

In the selective N-arylation of amines or azoles with aryl halidesa-, methyl-α-d-glucopyranoside (MG) was found to function as a green ligand of copper powder. In addition, nitrogen heterocyclic amine compounds can also undergo the N-arylation coupling with heterocyclic aryl chlorides. This process allows access to a variety of aromatic amines and aryl azoles under mild reaction conditions, has good tolerance, and proceeds in moderate to high yield.

Practical Catalytic Cleavage of C(sp3)?C(sp3) Bonds in Amines

The selective cleavage of thermodynamically stable C(sp3)?C(sp3) single bonds is rare compared to their ubiquitous formation. Herein, we describe a general methodology for such transformations using homogeneous copper-based catalysts in the presence of air. The utility of this novel methodology is demonstrated for Cα?Cβ bond scission in >70 amines with excellent functional group tolerance. This transformation establishes tertiary amines as a general synthon for amides and provides valuable possibilities for their scalable functionalization in, for example, natural products and bioactive molecules.

PRMT5 INHIBITORS AND USES THEREOF

Described herein are compounds of Formula (I), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. Compounds of the present invention are useful for inhibiting PRMT5 activity. Methods of using the compounds for treating PRMT5-mediated disorders are also described.