5238-27-7

Usage

Chemical Properties

clear colorless liquid

InChI:InChI=1/C6H11ClO/c1-3-4-5(2)6(7)8/h5H,3-4H2,1-2H3/t5-/m1/s1

Upstream product

• 1187-82-2 (S)-2-methylpentanoic acid 
• 97-61-0 2-Methylpentanoic acid 
• 4371-03-3 methylpropylmalonic acid 
• 7719-09-7 thionyl chloride 
• 49642-47-9 methyl (R)-2-methylbutyric acid 
• 109-52-4 valeric acid 

Downstream Products

• 51532-30-0 (S)-(+)-4-methylheptan-3-one 
• 6941-49-7 2-methylpentanamide 
• 2610-50-6 2-methyl-valeric acid anilide 
• 1689-96-9 3,5-Dichlor-4-(methyl-propylacetoxy)benzonitril 
• 53083-85-5 2-Methyl-pentanoic acid 2-(2,4-dimethyl-phenyl)-3-oxo-3H-inden-1-yl ester 
• 59518-02-4 2-Methyl-pentanoic acid [2-methyl-3-(2-methyl-pentanoylamino)-phenyl]-amide 
• 53083-72-0 2-Methyl-pentanoic acid 2-(2-chloro-phenyl)-3-oxo-3H-inden-1-yl ester 
• 1689-97-0 3,5-Dibrom-4-(methyl-propyl-acetoxy)benzonitril 
• 22132-34-9 2-Methyl-pentanoic acid (3-chloro-4-ethylsulfanyl-phenyl)-amide 
• 22133-25-1 2-Methyl-pentanoic acid (3-chloro-4-methylsulfanyl-phenyl)-amide 
• 71220-65-0 2-Methyl-pentanoic acid [3-(3-trifluoromethyl-phenoxymethyl)-phenyl]-amide 
• 90207-25-3 4-methyl-decan-5-one 
• 25228-14-2 2-Methyl-pentanoic acid [3-(3-methyl-ureido)-phenyl]-amide 
• 25228-85-7 2-Methyl-pentanoic acid (3-phenylacetylamino-phenyl)-amide 

Relevant academic research and scientific papers

Design, synthesis and agricultural evaluation of derivatives of N-Acyl-N-(m-fluoro-benzyl)-6-amino-coumarin

ABTRACT: This study aims to design and synthesize a series of N-Acyl-N-(m-fluoro- benzyl)-6- amino-coumarins through the principle of active substructure stitching, which are based on the core structure of N-(m-fluoro-benzyl)-6-amino-coumarin. The structures of target compounds e1–e25 have been characterized by 1H NMR, 13C NMR, ESI-MS and elemental analysis. Meanwhile, their agricultural activity have been evaluated in two weeds (Amaranth and Crabgrass) and four widespread noxious pathogens (V.mali, B.cinerea, F.axysporium and C.bacteria). The herbicidal activity results showed that almost all synthetic molecules have a greater impact on the stem system than on the root. Excellent inhibition rates were discovered from compounds e2–e5 and e20–e23 against Amaranth on stems, which were above 58percent(20 mg/L), 68percent(100 mg/L) respectively. Compounds e2 and e21 also exhibited striking inhibition on stems growth of both weeds. Anti-pathogenic activity showed that all the compounds exerted a better inhibitory activity on B.cinerea at 20 ppm compared to control carbendazim. All the heterocyclic substituted compounds (e17–e24, >57percent) made a better influence than the control (54.1percent) at the100 ppm. This research provides promising herbicidal and anti-pathogenic agents that have the better effects and can be potential for further development.

Discovery and Mechanism of Action of Small Molecule Inhibitors of Ceramidases**

Sphingolipid metabolism is tightly controlled by enzymes to regulate essential processes in human physiology. The central metabolite is ceramide, a pro-apoptotic lipid catabolized by ceramidase enzymes to produce pro-proliferative sphingosine-1-phosphate. Alkaline ceramidases are transmembrane enzymes that recently attracted attention for drug development in fatty liver diseases. However, due to their hydrophobic nature, no specific small molecule inhibitors have been reported. We present the discovery and mechanism of action of the first drug-like inhibitors of alkaline ceramidase 3 (ACER3). In particular, we chemically engineered novel fluorescent ceramide substrates enabling screening of large compound libraries and characterized enzyme:inhibitor interactions using mass spectrometry and MD simulations. In addition to revealing a new paradigm for inhibition of lipid metabolising enzymes with non-lipidic small molecules, our data lay the ground for targeting ACER3 in drug discovery efforts.

Photoinduced remote regioselective radical alkynylation of unactivated C-H bonds

A method for the remote regioselective alkynylation of unactivated C(sp3)-H bonds in diverse aliphatic amides by photogenerated amidyl radicals has been developed. The site-selectivity is dominated via a 1,5-hydrogen atom transfer (HAT) process of the amide. Mild reaction conditions and high regioselectivity are demonstrated in this methodology.

Functionalization of α-C(sp3)?H Bonds in Amides Using Radical Translocating Arylating Groups

α-C?H arylation of N-alkylamides using 2-iodoarylsulfonyl radical translocating arylating (RTA) groups is reported. The method allows the construction of α-quaternary carbon centers in amides. Various mono- and disubstituted RTA-groups are applied to the arylation of primary, secondary, and tertiary α-C(sp3)?H-bonds. These radical transformations proceed in good to excellent yields and the cascades comprise a 1,6-hydrogen atom transfer, followed by a 1,4-aryl migration with subsequent SO2 extrusion.

Remote Regioselective Radical C-H Functionalization of Unactivated C-H Bonds in Amides: The Synthesis of gem-Difluoroalkenes

The site-selective functionalization of unactivated aliphatic amines is an attractive and challenging synthetic approach. We herein report a general strategy for the remote site-selective functionalization of unactivated C(sp3)-H bonds in amides by photogenerated amidyl radicals to form gem-difluoroalkenes with trifluoromethyl-substituted alkenes. The site selectivity is controlled by a 1,5-hydrogen atom transfer (HAT) process of the amide. This photocatalyzed transformation shows both chemo- and site-selectivity, facilitating the formation of a secondary, tertiary, or quaternary carbon center.

Lappaconitine derivative with analgesic activity, and preparation method and application thereof

The invention provides a lappaconitine derivative with analgesic activity, and a preparation method and application thereof. The structure of the lappaconitine derivative is as shown in formula I in the specification. The lappaconitine derivative provided by the invention is high in analgesic activity, good in water solubility and low in biotoxicity, can be used for preparing low-toxicity analgesic drugs, and is wide in application prospect.

Visible-Light-Assisted Gold-Catalyzed Fluoroarylation of Allenoates

A strategically novel synthetic method for the fluoroarylation of allenic ester was developed that enables the expedient construction of a host of β-fluoroalkyl-containing cinnamate derivatives. The reaction proceeds through visible-light-promoted gold redox catalysis, occurs smoothly under very mild reaction conditions, accommodates a large variety of functional groups, and more importantly allows the incorporation of fluorine and aryl groups with excellent regio- and stereoselectivity. The concomitant activation mode for both the allene motif and the hydrogen fluoride is key for the success of the reaction.

2-Amino-5,6-difluorophenyl-1 H-pyrazole-Directed PdII Catalysis: Arylation of Unactivated β-C(sp3)-H Bonds

Palladium-catalyzed arylation of unactivated β-C(sp3)-H bonds in carboxylic acid derivatives with aryl iodides is described for the first time using 2-amino-5,6-difluorophenyl-1H-pyrazole as an efficient and readily removable directing group. Two fluoro groups are installed at the 5- and 6-position of the anilino moiety in 2-aminophenyl-1H-pyrazole, clearly enhancing the directing ability of the auxiliary. In addition, the protocol employs Cu(OAc)2/Ag3PO4 (1.2/0.3) as additives, evidently reducing the stoichiometric amount of expensive silver salts. Furthermore, this process exhibits high β-site selectivity, compatibility with diverse substrates containing α-hydrogen atoms, and excellent functional group tolerance.

Direct C-C Bond Formation from Alkanes Using Ni-Photoredox Catalysis

A method for direct cross coupling between unactivated C(sp3)-H bonds and chloroformates has been accomplished via nickel and photoredox catalysis. A diverse range of feedstock chemicals, such as (a)cyclic alkanes and toluenes, along with late-stage intermediates, undergo intermolecular C-C bond formation to afford esters under mild conditions using only 3 equiv of the C-H partner. Site selectivity is predictable according to bond strength and polarity trends that are consistent with the intermediacy of a chlorine radical as the hydrogen atom-abstracting species.

Methylation-dependent acyl transfer between polyketide synthase and nonribosomal peptide synthetase modules in fungal natural product biosynthesis

Biochemical studies of purified and dissected fungal polyketide synthase and nonribosomal peptide synthetase (PKS-NRPS) hybrid enzymes involved in biosynthesis of pseurotin and aspyridone indicate that one α-methylation step during polyketide synthesis is a prerequisite and a key checkpoint for chain transfer between PKS and NRPS modules. In the absence of the resulting γ-methyl feature, the completed polyketide intermediate is offloaded as an α-pyrone instead of being aminoacylated by the NRPS domain. These examples illustrate that precisely timed tailoring domain activities play critical roles in the overall programming of the iterative PKS (and NRPS) functions.