6279-84-1

Usage

Uses

Used in Organic Synthesis:
3-(3-methoxyphenoxy)propanenitrile is used as a versatile building block in organic synthesis for the development of a wide range of organic molecules. Its unique structure allows for the creation of various compounds with different properties and applications.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 3-(3-methoxyphenoxy)propanenitrile is used as an intermediate in the production of pharmaceuticals. Its potential biological activity and the presence of the nitrile functional group make it a valuable component in the synthesis of new drugs.
Used in Agrochemical Production:
3-(3-methoxyphenoxy)propanenitrile also finds applications in the agrochemical industry, where it is used as an intermediate in the synthesis of various agrochemicals. Its unique structure and functional groups can contribute to the development of effective and environmentally friendly products.

InChI:InChI=1/C10H11NO2/c1-12-9-4-2-5-10(8-9)13-7-3-6-11/h2,4-5,8H,3,7H2,1H3

Upstream product

• 150-19-6 O-methylresorcine 
• 107-13-1 acrylonitrile 
• 3245-45-2 1-(2-bromoethoxy)-3-methoxybenzene 
• 151-50-8 potassium cyanide 

Downstream Products

• 49855-03-0 3-(3-methoxyphenoxy)propionic acid 
• 6451-26-9 1-(3-aminopropoxy)-3-methoxybenzene 
• 37705-36-5 β-m-Methoxyphenoxyethylmethylketon 
• 37705-38-7 β-m-Methoxyphenoxyethylphenylketon 
• 18385-79-0 7-methoxy chroman-4-ol 
• 126398-51-4 7-methoxy-4-(phenylthio) chroman 
• 126398-56-9 7-methoxy-4-(phenylsulphonyl) chroman 
• 126398-60-5 7-methoxy-4-methyl-4-(phenylsulphonyl) chroman 
• 126398-62-7 4-allyl-7-methoxy-4-(phenylsulphonyl) chroman 
• 126398-63-8 4-benzyl-7-methoxy-4-(phenylsulphonyl) chroman 
• 126398-67-2 4-(2,4-dimethoxybenzoyl)-7-methoxy-4-(phenylsulphonyl) chroman 
• 10493-09-1 7,3',4'-trimethoxyflavanone 
• 25826-69-1 4',7-dimethoxyflavanone 
• 21785-09-1 7-methoxyflavanone 

Relevant academic research and scientific papers

Facile access to chiral 4-substituted chromanes through Rh-catalyzed asymmetric hydrogenation

Rh/ZhaoPhos-catalyzed asymmetric hydrogenation of a series of (E)-2-(chroman-4-ylidene)acetates was successfully developed to prepare various chiral 4-substituted chromanes with high yields and excellent enantioselectivities (up to 99percent yield, 98percent ee). Moreover, the gram-scale hydrogenation could be performed well in the presence of 0.02 molpercent catalyst loading (TON = 5000), the hydrogenation product was easily converted to access other important compounds, which demonstrated the synthetic utility of this asymmetric catalytic methodology.

Synthesis of Flavanones via Palladium(II)-Catalyzed One-Pot β-Arylation of Chromanones with Arylboronic Acids

A total of 47 flavanones were expediently synthesized via one-pot β-arylation of chromanones, a class of simple ketones possessing chemically unactivated β sites, with arylboronic acids via tandem palladium(II) catalysis. This reaction provides a novel route to various flavanones, including natural products such as naringenin trimethyl ether, in yields up to 92percent.

Studies towards the stereoselective α-hydroxylation of flavanones. Biosynthetic significance

The enolates of various propiophenones, chromanones, and also analogues of naturally occurring flavanones were stereoselectively hydroxylated at the ?-position, by employing commercially available enantiopure oxaziridines, to afford the desired ?-hydroxylated target molecules in good to exceptional stereoselectivities and in moderate to good chemical yields. A mechanistic rationale is presented to account for the stereoselectivities achieved. These in vitro results were tentatively related to the stereoselective biosynthesis of enantio-enriched dihydroflavonols while questions were raised about the authenticity of certain natural compounds. CSIRO 2008.

A NEW SYNTHETIC APPROACH TO THE ROTENOID RING SYSTEM

The (+)-cis-chromanochromanones (2) and (3), respresenting the basic ring system of the natural insecticide rotenone, have been synthesised by a general procedure; the key step is 4-aroylation of the 4-(phenyl-sulphonyl)chromans (7; Z=SO2Ph).

Studies in Antifertility Agents: Part XXIX - synthesis of 4--3-benzylchromans

7-H/Methoxy-4-chromanones (1, 2), obtained by PPA cyclization of the respective β-aryloxypropionic acids, on treatment with araldehydes (3, 4) give the corresponding 3-arylidene-4-chromanones (5, 6).Catalytic hydrogenation of 5 and 6 over Pd-C (10percent) with one mole of hydrogen affords 3-benzyl-4-chromanones (7, 8), while hydrogenation of 6 yields 3-benzyl-7-methoxychroman (9).NaBH4 reduction of 7 and 8 gives the corresponding 4-chromanols (10, 11) as a mixture of 3,4-cis- and -trans-isomers, which are arylated as such with PhOH-AlCl3 to give 4-(p-hydroxyphenyl)chromans(12, 13) as the main products.Treatment of 12 and 13 with Ac2O-pyridine and with p-NO2C6H4COCl-pyridine yields the corresponding p-acetoxy (14, 15) and p-nitrobenzoyloxy (16, 17) derivatives.Alkylation of 12 and 13 with N-(β-chloroethyl)pyrrolidine hydrochloride furnishes the title compounds, 4--3-(p-chloro/H)benzyl-7-H/methoxy-chromans (18, 19).None of these compounds prevents pregnancy at 5 mg/kg dose in rats.