65738-56-9

Usage

Uses

Used in Pesticide Synthesis:
Methyl 5-chloro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate is used as an intermediate in the synthesis of IN-KG 433 (I627995), which is an impurity of Indoxacarb (I654000). Indoxacarb is an oxadiazine pesticide that is effective against lepidopteran larvae and is utilized as the active ingredient in several household insecticides, including cockroach baits. Its role in the synthesis process is essential for creating effective pest control solutions.

InChI:InChI=1/C11H9ClO3/c1-15-11(14)9-5-6-4-7(12)2-3-8(6)10(9)13/h2-4,9H,5H2,1H3

Upstream product

• 42348-86-7 5-chloro-1-indanone 
• 1579-14-2 2-chloroindanone 
• 616-38-6 carbonic acid dimethyl ester 
• 122-01-0 4-chloro-benzoyl chloride 
• 292638-85-8 acrylic acid methyl ester 
• 103040-43-3 3-(3-chlorophenyl)propionic acid methyl ester 
• 42175-03-1 methyl ester of m-chlorocinnamic acid 
• 108-90-7 chlorobenzene 
• 3946-29-0 3,4'-Dichloropropiophenone 
• 252989-39-2 methyl 4-chloro-2-(3-methoxy-3-oxo-1-propanyl)-benzoate 

Downstream Products

• 144172-24-7 (R,S)‐5‐chloro‐1‐oxo‐2,3‐dihydro‐2‐hydroxy‐1H‐indene‐2‐carboxylic acid methyl ester 
• 871682-78-9 tert-butyl 5-chloro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate 
• 1228684-83-0 C₁₄H₁₃ClO₃ 
• 1261666-08-3 adamantyl 5-chloro-2,3-dihydro-1-oxo-1H-indene-2-carboxylate 
• 1429880-49-8 (R)-tert-butyl 5-chloro-1-oxo-2-(9H-xanthen-9-yl)-2,3-dihydro-1H-indene-2-carboxylate 
• 1429880-75-0 tert-butyl 5-chloro-1-oxo-2-(9H-xanthen-9-yl)-2,3-dihydro-1H-indene-2-carboxylate 

Relevant academic research and scientific papers

Enecarbamates as imine surrogates: Nucleophilic addition of 1,3-dicarbonyl compounds to enecarbamates

(Chemical Equation Presented) Novel Mannich-type reactions of 1,3-dicarbonyl compounds with enecarbamates have been developed. Stable and storable enecarbamates work as surrogates of aliphatic aldehyde-derived imines, which are known to be difficult to isolate and store.

Highly Selective Difluoromethylations of β-Keto Amides with -TMSCF 2Br under Mild Conditions

Without employing any transition metal and other additives, efficient methods for selective difluoromethylations of β-keto amides with TMSCF 2 Br reagent have been developed under mild conditions. This protocol allows a convenient access to various α-difluoromethyl β-keto amides with excellent yields (up to 93%) and high carbon/oxygen (C/O) regioselectivities (up to 99:1). The C/O selectivity of β-keto amides could be easily reversed and controlled by simply changing the base. This protocol can be easily scaled-up and the C-difluoromethylation product could be reduced into CF 2 H-containing amino alcohol derivatives. Moreover, the first enantioselective electrophilic difluoromethylation of β-keto amides has been achieved by phase-transfer catalysis.

Method for synthesizing methyl 6-chloro-3-oxo-1,2-dihydroindene-2-carboxylate by one-pot method

The invention discloses a method for synthesizing methyl 6-chloro-3-oxo-1,2-dihydroindene-2-carboxylate by one-pot method, thereby overcoming the technical defects of long synthesis route, multiple reaction steps, multiple generated three wastes, high difficulty in subsequent three waste treatment and the like in the prior art. methyl 6-chloro-3-oxo-1,2-dihydroindene-2-carboxylate is synthesizedfrom a substrate parachlorobenzoyl chloride and methyl acrylate by a one-pot method under the effect of lewis acid. A one-pot synthesis reaction is adopted, the reaction steps are few, operation is easy, raw materials are easy to obtain, and the method is economical, environmentally friendly and suitable for the current environmental protection requirement.

Ring-Strain-Enabled Catalytic Asymmetric Umpolung C-O Bond-Forming Reactions of 1,2-Oxazetidines for the Synthesis of Functionalized Chiral Ethers

An unprecedented catalytic asymmetric umpolung C-O bond-forming reaction of N-nosyl 1,2-oxazetidines with β-keto esters has been achieved in the presence of a chiral phase-transfer catalyst, allowing access to a range of highly functionalized chiral ethers bearing quaternary and no adjacent stereogenic centers with high yields, excellent enantioselectivities, and diastereoselectivities (up to 97percent ee and 20:1 dr). These versatile products could be flexibly transformed into biologically important chiral fused and spiro morpholines in two steps.

Highly Carbon-Selective Monofluoromethylation of β-Ketoesters with Fluoromethyl Iodide

A highly carbon-selective monofluoromethylation of a broad range of β-ketoesters with fluoromethyl iodide under mild conditions is described. The uses of lithium tert-butoxide as the base and diglyme as the solvent made great contributions to the high C/O regioselectivity.

Discovery of a Novel Series of Tricyclic Oxadiazine 4a-Methyl Esters Based on Indoxacarb as Potential Sodium Channel Blocker/Modulator Insecticides

Indoxacarb, a commercialized oxadiazine insecticide, nearly irreversibly blocks open/inactivated, but not resting sodium channels. The structure-activity relationships showed that the substituents at the position of the chiral atom in the oxadiazine ring are very important to the biological activity of oxadiazine insecticide. Here we synthesized a series of tricyclic oxadiazine 4a-methyl ester derivatives. The chiral atom in the oxadiazine ring has been epimerized and substituted with either pyrethric acid or cinnamic acid derivatives. Benzene ring in the tricyclic moiety was substituted with a chlorine, fluorine, or bromine atom, and nitrogen-linked benzene ring was substituted with a trifluoromethyl or trifluoromethoxy group. Toxicity of these compounds against Spodoptera litura F. was evaluated. Diastereoisomers of most toxic compounds J7 and J9 with pyrethric acid moiety were separated by flash column chromatography. The more polar diastereoisomers, J7-L-Rf and J9-L-Rf, and compounds J24 and J26 with cinnamic acid moiety exhibited highest insecticidal activities. We further used Monte Carlo energy minimizations to dock compound J7 and J24 in the NavMs-based homology model of the open cockroach sodium channel. In the low-energy binding modes, the compound interacted with residues in the inner pore and domain interfaces, which previously were proposed to contribute to receptors of pyrethroids and sodium channel blocker insecticides. Our results define compound J7 and J24 as a potentially useful optimized hit for the development of multiple sites sodium channel blocker or modulator.

Whole-cell biocatalytic of Bacillus cereus WZZ006 strain to synthesis of indoxacarb intermediate: (S)-5-Chloro-1-oxo-2,3-dihydro-2-hydroxy-1H-indene-2-carboxylic acid methyl ester

In this study, a newly isolated strain screened from the indoxacarb-rich agricultural soils, Bacillus cereus WZZ006, has a high stereoselectivity to racemic substrate 5-chloro-1-oxo-2,3-dihydro-2-hydroxy-1H-indene-2-carboxylic acid methyl ester. (S)-5-chloro-1-oxo-2,3-dihydro-2-hydroxy-1H-indene-2-carboxylic acid methyl ester was obtained by bio-enzymatic resolution. After the 36-hour hydrolysis in 50-mM racemic substrate under the optimized reaction conditions, the e.e.s was up to 93.0% and the conversion was nearly 53.0% with the E being 35.0. Therefore, B cereus WZZ006 performed high-level ability to produce (S)-5-chloro-1-oxo-2,3-dihydro-2-hydroxy-1H-indene-2-carboxylic acid methyl ester. This study demonstrates a new biocatalytic process route for preparing the indoxacarb chiral intermediates and provides a theoretical basis for the application of new insecticides in agricultural production.

Oxadiazine cinnamate derivatives as well as preparation method and application thereof

The invention provides oxadiazine cinnamate derivatives as well as a preparation method and application thereof. The molecular structures of the oxadiazine cinnamate derivatives are shown in a formula(I) described in the description, wherein R1 is hydrogen, halogen, an alkyl group having 1-4 carbon atoms, alkoxy having 1-4 carbon atoms or an amino group; R2 is -CF3, -OCF3 or -OCH2F. The preparation method provided by the invention combines indoxacarb with cinnamic acid so as to obtain the oxadiazine cinnamate derivatives by rationally designing the structure of the indoxacarb; the oxadiazinecinnamate derivatives not only can significantly increase the poisonous activity of prodenia litura, but also has good biological activity against mosquitoes with drug resistance; compared with commercial indoxacarb insecticide, the poisonous activity of the compounds against pests is greatly enhanced, and the biological activity of the compounds for drug-resistant pests is especially enhanced, sothat drug protection is provided for the prevention and control of the resistant pests. Furthermore, the raw materials used in the method for producing the compounds provided by invention are readilyavailable, the reaction conditions are mild, and the yield of the target product is high.

Method for catalytic oxidation of indanone-2-formate under micro-reaction conditions or conventional reaction conditions

The invention provides a method for catalytic oxidation of indanone-2-formate under micro-reaction conditions or conventional reaction conditions, belonging to the technical field of organic chemicalsynthesis. The method comprises the following steps: mixing the indanone-2-formate, a catalyst and a solvent so as to obtain a homogeneous solution; dissolving an oxidizing agent with a solvent, and carrying out extraction and drying so as to obtain a homogeneous solution; allowing two above-mentioned homogeneous solutions to react under the micro-reaction conditions or the conventional reaction reactions so as to obtain a reaction solution; and adjusting the pH value of the above-mentioned reaction solution to 6.5 to 7.5 with hydrochloric acid with a mass fraction of 10%, carrying out stirring for 20 to 30 minutes, then carrying out cooling to 5 DEG C or below, carrying out filtering, flushing a filter cake with a solvent with a temperature of 0 to 5 DEG C, and carrying out drying so as to obtain the indanone-2-hydroxy-2-formate. According to the invention, by utilization of the highly-efficient thermal mass transfer ability of a microchannel reactor, and combination of combined catalytic oxidation of chiral phosphorylimidic acid and organic base, compared with a conventional preparation method, the method provided by the invention has excellent effects of simple process operation, high catalytic oxidation efficiency, short reaction time, simple equipment, high safety and obtainment of a product with high chiral purity.

Highly Enantioselective α-Cyanation with 4-Acetylphenyl Cyanate

A highly effective asymmetric version of α-cyanation of β-keto esters and amides was developed with a Lewis-acid catalyst. Thus, by using 10 mol % of a tridentate bisoxazoline–zinc(II) complex as the catalyst, a series of chiral nitriles containing a quaternary carbon center were obtained in excellent enantioselectivities (up to 97 % enantiomeric excess) and up to 95 % yield in the presence of 4 ? molar sieve at room temperature. For the first time, mild and active 4-acetylphenyl cyanate was used instead of cyano-hyperiodinate as the cationic cyano source for catalytic asymmetric α-cyanation.