6836-18-6

Usage

Uses

Used in Pharmaceutical Industry:
4-(4-Methoxyphenyl) butyl chloride is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its butyl chain and chlorine atom make it a valuable building block in organic chemistry, enabling the formation of diverse compounds with potential therapeutic applications.
Used in Organic Chemistry:
In the field of organic chemistry, 4-(4-Methoxyphenyl) butyl chloride is used as a versatile reagent for the synthesis of a wide range of organic compounds. Its ability to undergo various reactions allows for the creation of new molecules with different properties and potential applications in various industries.

InChI:InChI=1/C11H13ClO2/c1-14-10-7-5-9(6-8-10)3-2-4-11(12)13/h5-8H,2-4H2,1H3

Upstream product

• 4521-28-2 4-(4-Methoxyphenyl)butyric acid 
• 26153-41-3 γ-(4-methoxyphenyl)-γ-butyrolactone 

Downstream Products

• 71501-17-2 1,4-bis(4-methoxyphenyl)butan-1-one 
• 6836-19-7 7-Methoxy-1-tetralone 
• 38519-37-8 2-(3-(4-methoxyphenyl)propyl)benzo[d]thiazole 
• 113379-23-0 5-[4-(4-Methoxy-phenyl)-butyryl]-pyrimidine-2,4,6-trione 
• 103831-06-7 O-methyl 4-(p-methoxyphenyl)butyrohydroxamate 
• 1026090-42-5 2-(3-chloro-phenyl)-6-(4-methoxy-phenyl)-3-oxo-hexanenitrile 
• 5701-83-7 1,4-bis(4-methoxyphenyl)butane 
• 187269-85-8 1,4-bis-[3-(3-carbomethoxymethylphenyl)-4-hydroxyphenyl]butane 
• 187269-83-6 1,4-bis-[3-(3-carbomethoxymethylphenyl)-(4-methoxy)phenyl]butane 
• 187269-88-1 1,4-bis-[3-(3-carbomethoxymethylphenyl)-4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]butane 
• 95333-55-4 1-[4-(4-Hydroxy-phenyl)-butyl]-1,3-dihydro-imidazole-2-thione 
• 104489-45-4 1-[4-(4-Methoxy-phenyl)-butyl]-1,3-dihydro-imidazole-2-thione 
• 112403-72-2 O-methyl N-chloro-4-(p-methoxyphenyl)butyrohydroxamate 
• 19393-87-4 8-methylnaphthalen-2-ol 

Relevant academic research and scientific papers

Photoinduced Aerobic Iodoarene-Catalyzed Spirocyclization of N-Oxy-amides to N-Fused Spirolactams**

Iodoarene catalysis is a powerful methodology that usually requires an excess of oxidant, or of redox mediator if the terminal oxidant is dioxygen, to generate the key hypervalent iodine intermediate to proceed efficiently. We report that, using the spiro-cyclization of amides as a benchmark reaction, aerobic iodoarene catalysis can be enabled by relying on a pyrylium photocatalyst under blue light irradiation. This unprecedented dual organocatalytic system allows the use of low catalytic loading of both catalysts under very mild operating conditions.

Enantioselective Remote C(sp3)-H Cyanation via Dual Photoredox and Copper Catalysis

The remote C(sp3)-H cyanation of carboxamides has been described by merging photoredox and copper catalysis in a site-selective and enantiocontrolled manner. The protocol is the integration of photoinduced and nitrogen-centered radical-mediated intermolecular hydrogen atom transfer with chiral copper-complex-catalyzed radical cyanation. This strategy gives enantio-enriched cyanated amides in high yields.

Green synthesis method of medical intermediate benzocyclohexanone compound

The invention provides a green synthesis method of a benzocyclohexanone compound, and belongs to the technical field of organic synthesis. The method provided by the invention comprises the followingsteps: by taking 4-phenylbutyric acid as a raw material, firstly carrying out reflux reaction with oxalyl chloride in dichloromethane, carrying out vacuum evaporation to dryness to obtain a crude product of the 4-phenylbutyryl chloride compound, then dissolving the crude product in a solvent, adding a metal-doped modified molecular sieve catalyst to start reaction, and stirring the solution at different temperatures to carry out ring closing reaction, thereby obtaining the product; and after the reaction is finished, carrying out suction filtration, solvent washing, column chromatography purification and other operations to obtain the target product benzocyclohexanone compound. The synthesis method disclosed by the invention is environment-friendly in reaction and simple and convenient tooperate, the catalyst can be recycled, and the synthesis method is suitable for green synthesis of the benzocyclohexanone compound.

Ruthenium(II)-Catalyzed Enantioselective ?-Lactams Formation by Intramolecular C-H Amidation of 1,4,2-Dioxazol-5-Ones

We report the Ru-Catalyzed enantioselective annulation of 1,4,2-Dioxazol-5-Ones to furnish ?-Lactams in up to 97% yield and 98% ee via intramolecular carbonylnitrene C-H insertion. By employing chiral diphenylethylene diamine (dpen) as ligands bearing electron-Withdrawing arylsulfonyl substituents, the reactions occur with remarkable chemo- A nd enantioselectivities; the competing Curtius-Type rearrangement was largely suppressed. Enantioselective nitrene insertion to allylic/propargylic C-H bonds was also achieved with remarkable tolerance to the Ca?C and Ca‰iC bonds.

Ruthenium(II)-Catalyzed Enantioselective γ-Lactams Formation by Intramolecular C-H Amidation of 1,4,2-Dioxazol-5-ones

We report the Ru-catalyzed enantioselective annulation of 1,4,2-dioxazol-5-ones to furnish γ-lactams in up to 97% yield and 98% ee via intramolecular carbonylnitrene C - H insertion. By employing chiral diphenylethylene diamine (dpen) as ligands bearing electron-withdrawing arylsulfonyl substituents, the reactions occur with remarkable chemo- and enantioselectivities; the competing Curtius-type rearrangement was largely suppressed. Enantioselective nitrene insertion to allylic/propargylic C - H bonds was also achieved with remarkable tolerance to the C=C and C=C bonds.

Strategic Approach to the Metamorphosis of γ-Lactones to NH γ-Lactams via Reductive Cleavage and C-H Amidation

A new approach has elaborated on the conversion of γ-lactones to the corresponding NH γ-lactams that can serve as γ-lactone bioisosteres. This approach consists of reductive C-O cleavage and an Ir-catalyzed C-H amidation, offering a powerful synthetic tool for accessing a wide range of valuable NH γ-lactam building blocks starting from γ-lactones. The synthetic utility was further demonstrated by the late-stage transformation of complex bioactive molecules and the asymmetric transformation.

Non- C2-Symmetric Chiral-at-Ruthenium Catalyst for Highly Efficient Enantioselective Intramolecular C(sp3)-H Amidation

A new class of chiral ruthenium catalysts is introduced in which ruthenium is cyclometalated by two 7-methyl-1,7-phenanthrolinium heterocycles, resulting in chelating pyridylidene remote N-heterocyclic carbene ligands (rNHCs). The overall chirality results from a stereogenic metal center featuring either a or Δabsolute configuration. This work features the importance of the relative metal-centered stereochemistry. Only the non-C2-symmetric chiral-at-ruthenium complexes display unprecedented catalytic activity for the intramolecular C(sp3)-H amidation of 1,4,2-dioxazol-5-ones to provide chiral -lactams with up to 99:1 er and catalyst loadings down to 0.005 mol % (up to 11 ?200 TON), while the C2-symmetric diastereomer favors an undesired Curtius-type rearrangement. DFT calculations elucidate the origins of the superior C-H amidation reactivity displayed by the non-C2-symmetric catalysts compared to related C2-symmetric counterparts.

Discovery of Cytochrome P450 4F11 Activated Inhibitors of Stearoyl Coenzyme A Desaturase

Stearoyl-CoA desaturase (SCD) catalyzes the first step in the conversion of saturated fatty acids to unsaturated fatty acids. Unsaturated fatty acids are required for membrane integrity and for cell proliferation. For these reasons, inhibitors of SCD represent potential treatments for cancer. However, systemically active SCD inhibitors result in skin toxicity, which presents an obstacle to their development. We recently described a series of oxalic acid diamides that are converted into active SCD inhibitors within a subset of cancers by CYP4F11-mediated metabolism. Herein, we describe the optimization of the oxalic acid diamides and related N-acyl ureas and an analysis of the structure-activity relationships related to metabolic activation and SCD inhibition.

Rhodium-Catalyzed Decarbonylative Borylation of Aromatic Thioesters for Facile Diversification of Aromatic Carboxylic Acids

Transformation of aromatic thioesters into arylboronic esters was achieved efficiently using a rhodium catalyst. The broad functional-group tolerance and mild conditions of the method have allowed for the two-step decarboxylative borylation of a wide range of aromatic carboxylic acids, including commercially available drugs.

Selective α-Oxyamination and Hydroxylation of Aliphatic Amides

Compared to the α-functionalization of aldehydes, ketones, even esters, the direct α-modification of amides is still a challenge because of the low acidity of α-CH groups. The α-functionalization of N?H (primary and secondary) amides, containing both an unactived α-C?H bond and a competitively active N?H bond, remains elusive. Shown herein is the general and efficient oxidative α-oxyamination and hydroxylation of aliphatic amides including secondary N?H amides. This transition-metal-free chemistry with high chemoselectivity provides an efficient approach to α-hydroxy amides. This oxidative protocol significantly enables the selective functionalization of inert α-C?H bonds with the complete preservation of active N?H bond.