35180-14-4

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Benzyl-2,3-dihydro-1H-isoindole is utilized as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic applications.
Used in Organic Chemistry Research:
In the field of organic chemistry, 2-Benzyl-2,3-dihydro-1H-isoindole is employed as a valuable compound for studying and conducting various chemical reactions, thereby aiding in the advancement of chemical knowledge and innovation.
Used in Medicinal Chemistry:
2-Benzyl-2,3-dihydro-1H-isoindole is used as a scaffold in medicinal chemistry for the design and development of novel therapeutic agents, leveraging its structural features to enhance drug efficacy and selectivity.
Used in Chemical Reactions and Processes:
2-BENZYL-2,3-DIHYDRO-1H-ISOINDOLE is also applied in various chemical reactions and processes, serving as a versatile component that can be modified or combined with other molecules to achieve desired outcomes in chemical synthesis and material development.

InChI:InChI=1/C15H15N/c1-2-6-13(7-3-1)10-16-11-14-8-4-5-9-15(14)12-16/h1-9H,10-12H2

Upstream product

• 496-12-8 isoindoline 
• 100-39-0 benzyl bromide 
• 2142-01-0 N-benzylphthalimide 
• 13380-32-0 2-benzylisoindolin-1-one 
• 91-13-4 α,α'-dibromo-o-xylene 
• 100-46-9 benzylamine 
• 612-14-6 phthalyl alcohol 
• 119-67-5 o-carboxybenzaldehyde 

Downstream Products

• 496-12-8 isoindoline 
• 17448-14-5 2-benzyl-3-hydroxy-2,3-dihydro-isoindol-1-one 
• 13380-32-0 2-benzylisoindolin-1-one 
• 2142-01-0 N-benzylphthalimide 
• 100-39-0 benzyl bromide 

Relevant academic research and scientific papers

Oxidative Desymmetrization of Isoindolines Realized by tert -Butyl Nitrite (TBN) Initiated Radical sp 3C-H Activation Relay (CHAR)

An oxidative desymmetrization of isoindolines was realized by TBN initiated radical sp 3C-H activation relay (CHAR), providing a series of ω-hydroxylactams in high yields. This reaction exhibits broad substrate scope and functional group tolerance, and even N -alkyl iso-indolines can be well tolerated. The mechanistic study shows that the C-H bond oxidation, dioxygen trapping and intramolecular 1,5-H shift might be the key steps to achieve the oxidative desymmetrization.

A class of GPR40 agonist compounds with amide structure, and uses thereof

The present invention relates to a class of amide compounds with a novel structure, and a pharmaceutical composition thereof, wherein the structure of the amide compound is represented by a general formula (I). According to the present invention, the amide compound (I) can regulate GPR40 activity, and can be used for GPR40 activity related diseases such as diabetes and metabolic syndrome. The formula I is defined in the specification.

Isoindolinone Synthesis: Selective Dioxane-Mediated Aerobic Oxidation of Isoindolines

N-Alkyl and N-aryl-isoindolinones were prepared by a dioxane-mediated oxidation of isoindoline precursors. The transformation exhibits unique chemoselectivity for isoindonlines. A chiral tertiary (3°)-benzylic position was not racemized during oxidation, and methyl indoprofen was prepared by late stage oxidation. Mechanistic studies suggest a selective H atom transfer, which avoids many known oxidation (by-)products of isoindolinones.

Visible-Light-Mediated C(sp3)–H Thiocarbonylation for Thiolactam Preparation with Potassium Sulfide

We report herein a protocol for thiolactam preparation with potassium sulfide via visible-light-mediated C(sp3)–H thiocarbonylation, in which polysulfide dianions and radical anions generated from potassium sulfide were the key active species. A variety of thiolactams were straightforward established under mild conditions. Moreover, it was successfully applied to structural modification of tetrahydroberberine.

Iron-Catalysed Switchable Synthesis of Pyrrolidines vs Pyrrolidinones by Reductive Amination of Levulinic Acid Derivatives via Hydrosilylation

A selective production of pyrrolidines vs pyrrolidinones via hydrosilylation of levulinic acid and levulinates by switching of the iron complex catalyst is presented herein. The reactions proceeded efficiently with various anilines and alkylamines under both visible light irradiation and thermal conditions with 43 examples in isolated yields up to 93%. Noticeably, under similar conditions, cyclic amines such as piperidines and azepanes were efficiently synthesized with yields up to 92%, by reaction of anilines with 1,5- or 1,6-keto acids, respectively. Similarly, N-arylinsolidoline compounds can be prepared from 2-formylbenzoic acid in 57–93% yields. (Figure presented.).

Tri(pentaflurophenyl)borane-catalyzed reduction of cyclic imides with hydrosilanes: Synthesis of pyrrolidines

B(C6F5)3-catalyzed hydrosilylation of cyclic imides afforded an efficient synthetic method of pyrrolidines. In the presence of 5 mol% B(C6F5)3, various aromatic, aliphatic and polycyclic imides were smoothly reduced by PhSiH3 to generate the corresponding pyrrolidines in high yields. The reaction profiles monitored by 1H NMR spectroscopy disclosed the reduction process of cyclic imides and the effect of difference structure of the hydrosilanes on the hydrosilylation.

Reduction of Benzolactams to Isoindoles via an Alkoxide-Catalyzed Hydrosilylation

An alkoxide-catalyzed reduction of benzolactams to isoindoles with silanes was realized. With t-BuOK as the catalyst and Ph2SiH2 as the reductant, a series of benzolactams containing different functional groups were reduced to the co

Pyrrolidines compound and its synthesis method (by machine translation)

A pyrrolidine compound and its synthetic method, will be dissolved in an organic solvent in the cyclic imide compound with hydrogen as a reducing agent of the reagent and a Lewis acid as a catalyst mixing, under the condition of refluxing to prepare the aromatic ring and fat ring pyrrolidines. Synthetic route of this invention is simple, efficient and economic, mild condition, wide applicability, to pyrrolidines compound at the later stage of industrial production will play a great role in promoting. (by machine translation)

7-Azabicyclo[2.2.1]heptane as a structural motif to block mutagenicity of nitrosamines

Nitrosamines are potent carcinogens and toxicants in the rat and potential genotoxins in humans. They are metabolically activated by hydroxylation at an α-carbon atom with respect to the nitrosoamino group, catalyzed by cytochrome P450. However, there has been little systematic investigation of the structure-mutagenic activity relationship of N-nitrosamines. Herein, we evaluated the mutagenicity of a series of 7-azabicyclo[2.2.1]heptane N-nitrosamines and related monocyclic nitrosamines by using the Ames assay. Our results show that the N-nitrosamine functionality embedded in the bicyclic 7-azabicylo[2.2.1]heptane structure lacks mutagenicity, that is, it is inert to α-hydroxylation, which is the trigger of mutagenic events. Further, the calculated α-C-H bond dissociation energies of the bicyclic nitrosamines are larger in magnitude than those of the corresponding monocyclic nitrosamines and N-nitrosodimethylamine by as much as 20-30 kcal/mol. These results are consistent with lower α-C-H bond reactivity of the bicyclic nitrosamines. Thus, the 7-azabicyclo[2.2.1]heptane structural motif may be useful for the design of nongenotoxic nitrosamine compounds with potential biological/medicinal applications.

Selective catalytic monoreduction of phthalimides and imidazolidine-2,4- diones

Fluoride's new role: Selective and efficient monoreductions of imides can be achieved with polymethylhydrosiloxane (PMHS) and tetra-n-butylammonium fluoride (TBAF) as catalyst (see scheme). The system is characterized by good chemoselectivity, operational