61362-78-5

Upstream product

• 6836-19-7 7-Methoxy-1-tetralone 

Downstream Products

• 2436-96-6 1-nitro-2-(2-nitrophenyl)benzene 
• 2891-37-4 2,2'-dimethoxy-6,6',7,7'-5H,5'H-[1,1]binaphthalenyl-8,8'-dione 
• 1352285-83-6 1-bromo-2-methoxy-7-phenyl-5,6-dihydrobenzo[c]acridine 
• 1352285-85-8 2,2'-dimethoxy-7,7'-diphenyl-5,5',6,6'-tetrahydro-1,1'-bibenzo[c]acridine 

Relevant academic research and scientific papers

Click and Patterned Functionalization of Graphene by Diels-Alder Reaction

Chemical functionalization is a promising approach to controllably manipulate the characteristics of graphene. Here, we designed cis-dienes, featuring two dihydronaphthalene backbones, to decorate a graphene surface via Diels-Alder (DA) click reaction. The installation of a diene moiety into a nonplanar molecular structure to form cis-conformation enables a rapid (-5 min) DA reaction between graphene and diene groups. Patterned graphene of sub-micrometer resolution can be obtained by easily soaking poly(methyl methacrylate)-masked graphene in solution of hydroxyl-substituted cis-diene at room temperature. The functionalization degree can be further controlled by carrying out the reaction at higher temperature. The present result gives important insight into the effect of molecular conformation on the graphene functionalization process, and provides an effective and facile method for graphene functionalization.

Synthesis, Structures, Resolution, and Chiroptical Properties of 1,16-Diaryl-Substituted Benzo[5]helicene Derivatives

An efficient route to the synthesis of benzo[5]helicene derivatives functionalized on the interior side of the helix was developed, and resulted in a series of 1,16-diaryl-substituted benzo[5]helicene derivatives starting from easily available 7-methoxytetralone. X-ray crystal structures showed that the benzo[5]helicene derivatives had highly helical, twisted structures, and could all create hierarchical packing architectures with alternating P and M layers in the solid state. Moreover, seven pairs of enantiomers based on 1,16-diaryl-substituted benzo[5]helicene derivatives were also obtained by efficient resolution through HPLC with semipreparative chiral columns. The enantiomers all showed clear mirror-image circular dichroism (CD) spectra and high specific optical rotations, and their absolute configurations were determined by X-ray crystallography. Interestingly, a helical nanotubular structure was formed by the self-assembly of one enantiomer through halogen bonding. Furthermore, the enantiomers were found to have high racemization barriers and thermostability, which might be caused by the introduction of aryl substituents at the C1(C16) position.

Preparative resolution of (±)-bis-tetralone by means of autoseeded preferential crystallization induced by solvent evaporation (ASPreCISE)

(±)-Bis-tetralone (BisT) crystallizes as a stable conglomerate that can be resolved by preferential crystallization. This preferential crystallization was performed by autoseeded polythermic programmed preferential crystallization (AS3PC) and autoseeded preferential crystallization induced by solvent evaporation (ASPreCISE) variants in dimethylformamide and dichloromethane. Prior to performance of these resolutions, an extensive purification was necessary because the presence of impurities had a strong negative impact on the stereoselective crystal growth. Moreover, the presence of multiepitaxy phenomena required a vigorous stirring during the preferential crystallization in order to avoid a poor optical purity of the crops. Several preferential crystallization attempts demonstrate that ASPreCISE is recommended when there is an unfavorable variation of solubility versus temperature or when chemical degradation occurs on heating.

A dinaphtho[8,1,2-cde:2′,1′,8′-uva]pentacene derivative and analogues: synthesis, structures, photophysical and electrochemical properties

Dinaphtho[8,1,2-cde:2′,1′,8′-uva]pentacene and analogues as a new type of acene derivatives with scorpion-shaped structures were conveniently synthesized. Their structures, photophysical and electrochemical properties were experimentally and theoretically investigated. It was found that the pentacene derivative has a twisted configuration, but shows marked intermolecular π-π interactions, strong electronic delocalization, and a small HOMO-LUMO bandgap, which are different from those of pentacene and pentatwistacene derivatives with similar structures.

Design, synthesis and melatoninergic potency of new N-acyl 8,9-dihydro-4-methoxy-7H-2-benzo[de]quinolinalkanamines

A series of new N-acyl 8,9-dihydro-4-methoxy-7H-2-benzo[de]quinolinalkanamines have been prepared and tested for their ability to activate pigment granule aggregation in Xenopus laevis melanophores and bind to the recombinant human MT1 and MT2 melatonin receptor subtypes expressed in NIH 3T3 cells. Compounds with a single methylene spacer in the side chain (7) have no agonist activity, but are weak antagonists in the Xenopus melanophore assay, irrespectively of the size or shape of the R substituent (R = CH3 to c-C4H7). In contrast, compounds with two (8) or three (9) methylene spacers show partial agonist activity, though this does vary with the nature of the R substituent. Interestingly, the cyclopropane and cyclobutane R substituents, which are usually linked with antagonism, render the cyclopropanecarboxamido analog 9d and its cyclobutanecarboxamido congener 9e weak agonists. It seems, therefore, that in these compounds the R substituent constitutes a functional probe in the dynamic agonist-antagonist conformational equilibrium. One of the new molecules, antagonist 8c, exhibits a noteworthy MT2 subtype selectivity (13-fold), whereas the acetamido analog 9a (with a three methylene units spacer) also acts as an antagonist and is the only analog exhibiting MT1 selectivity (>10-fold). In contrast to the analogous N1-C7 annulated indole derivatives, recently reported, the new C1-C8 condensed isoquinolines are not all pure antagonists. Despite their modest receptor affinity at the binding site these compounds demonstrate that the nature of the response (agonist or antagonist activity) is dependent, in this case, on both the side chain spacer's length and the size and shape of the R group.

Multiple Absolute Stereocontrol in Cascade Lactone Formation via Dynamic Kinetic Resolution Driven by the Asymmetric Transfer Hydrogenation of Keto Acids with Oxo-Tethered Ruthenium Catalysts

A straightforward asymmetric construction of chiral fused γ- and δ-lactones containing multiple contiguous stereocenters was successfully developed by either (1) the dynamic kinetic resolution-asymmetric transfer hydrogenation (DKR-ATH) reaction using oxo

Central-to-Helical-to-Axial-to-Central Transfer of Chirality with a Photoresponsive Catalyst

Recent advances in molecular design have displayed striking examples of dynamic chirality transfer between various elements of chirality, e.g., from central to either helical or axial chirality and vice versa. While considerable progress in atroposelective synthesis has been made, it is intriguing to design chiral molecular switches able to provide selective and dynamic control of axial chirality with an external stimulus to modulate stereochemical functions. Here, we report the synthesis and characterization of a photoresponsive bis(2-phenol)-substituted molecular switch 1. The unique design exhibits a dynamic hybrid central-helical-axial transfer of chirality. The change of preferential axial chirality in the biaryl motif is coupled to the reversible switching of helicity of the overcrowded alkene core, dictated by the fixed stereogenic center. The potential for dynamic control of axial chirality was demonstrated by using (R)-1 as switchable catalyst to direct the stereochemical outcome of the catalytic enantioselective addition of diethylzinc to aromatic aldehydes, with successful reversal of enantioselectivity for several substrates.

Revisiting secondary interactions in neighboring group participation, exemplified by reactivity changes of iminylium intermediates

Neighboring group participation is defined as the action of a substituent to stabilize a transition state or an intermediate by forming a bond or a partial bond with the reaction center. In addition to the primary interaction with the nearest neighboring group, secondary interactions involving another neighboring group(s) could also occur in principle. Here, we revisit this issue by examining the influence of secondary interactions on the stability and reactivity of the putative iminylium cation intermediates, formed by N-O bond cleavage of 1-tetralone oxime systems. A direct observation of a peri-bromo-iminylium intermediate in solution supported the involvement of iminylium cations and the stabilizing effect of secondary interactions arising from a distal tandem substituent. Both experimental and computational findings support the idea that secondary interactions of a tandem-neighboring group on the primary peri-heteroatom (Br, Cl, and O(Me))-iminylium bonding interaction, i.e., a weak halogen bonding interaction (ester (nitro) oxygen-halogen bonding) and an unprecedented hydrogen bonding interaction between a nitro oxygen atom and a CH3O hydrogen atom, are crucial determinants of the reaction pathway, leading to either overwhelmingly selective syn-migration of the oxime functionality or covalent bond formation under acid-catalyzed Beckmann rearrangement conditions.

Helicene diphenol hydride, method for preparing same and application of helicene diphenol hydride

The invention discloses helicene diphenol hydride, a method for preparing the same and application of the helicene diphenol. A structural formula of the helicene diphenol hydride is shown as a formula I, wherein an R represents hydrogen atoms or bromine a

Carboxylic acid compound, and the basic photobase generator containing a photosensitive resin composition

PROBLEM TO BE SOLVED: To provide a carboxylic acid compound which has excellent reaction efficiency without generating carbon dioxide when generating a base, a base generator and a photosensitive resin composition containing the base generator. SOLU