Tag: M.W=200-250

Shang, Le-Le; Feng, Yun; Gao, Xing-Lian; Chen, Zi-Ren; Xia, Yu; Jin, Wei-Wei; Liu, Chen-Jiang published the artcile< DMAP-Catalyzed C-N Bond formation for Diverse synthesis of Imidazo[1,2-a]pyrimidine and Pyrimido[1,2-a]benzimidazole Derivatives.>, Synthetic Route of 3893-18-3, the main research area is haloalkenyl carbonyl compound aminobenzimidazole DMAP catalyst cyclocondensation reaction; imidazopyrimidine preparation green chem; aminoimidazole haloalkenyl carbonyl compound DMAP catalyst cyclocondensation reaction; pyrimidobenzimidazole preparation green chem.

A DMAP (2-dimethylaminopyridine)-catalyzed condensation reactions for the successful direct construction of pyrimido[1,2-a]benzimidazole or imidazo[1,2-a]pyrimidine was developed. The method utilized readily available α-bromocinnamaldehydes with 2-aminobenzimidazole or 2-aminoimidazole as starting materials in the presence of 2-DMAP/TBHP. In the process, two C-N bonds were successfully constructed to synthesize target compounds

Chinese Journal of Chemistry published new progress about Benzimidazoles Role: RCT (Reactant), RACT (Reactant or Reagent). 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Synthetic Route of 3893-18-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Oi, Miku; Takita, Ryo; Kanazawa, Junichiro; Muranaka, Atsuya; Wang, Chao; Uchiyama, Masanobu published the artcile< Organocopper cross-coupling reaction for C-C bond formation on highly sterically hindered structures>, Product Details of C7H7BrO2S, the main research area is organocopper compound aryl iodide cross coupling reaction mechanism.

A powerful, broadly applicable cross-coupling protocol that enabled carbon-carbon bond formation at highly sterically hindered carbon centers (both sp2 and sp3) by employing organocopper reagents under palladium catalysis was described. Exptl. studies and theor. calculations indicated that the key to the unique reactivity of copper was the relatively low activation energy of the compact transmetalation transition state, due to Cu(I)-Pd(II) interaction, which was associated with small values of deformation energy of the reactants. This reaction was applicable to a variety of bulky substrates, including compounds inert to previous cross-coupling chem. and has high functional group tolerance.

Chemical Science published new progress about Aryl bromides Role: PRP (Properties), RCT (Reactant), RACT (Reactant or Reagent). 5751-83-7 belongs to class bromides-buliding-blocks, and the molecular formula is C7H7BrO2S, Product Details of C7H7BrO2S.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Wang, Na; Zhang, Wei; Zhou, Long-Hua; Deng, Qing-Feng; Xie, Zong-Bo; Yu, Xiao-Qi published the artcile< One-Pot Lipase-Catalyzed Aldol Reaction Combination of In Situ Formed Acetaldehyde>, Category: bromides-buliding-blocks, the main research area is lipase aldol condensation addition acetaldehyde aldehyde.

A facile tandem route to α,β-unsaturated aldehydes was developed by combining the two catalytic activities of the same enzyme in a one-pot strategy for the aldol reaction and in situ generation of acetaldehyde. Lipase from Mucor miehei was found to have conventional and promiscuous catalytic activities for the hydrolysis of vinyl acetate and aldol condensation with in situ formed acetaldehyde. The first reaction continuously provided material for the second reaction, which effectively reduced the volatilization loss, oxidation, and polymerization of acetaldehyde, as well as avoided a neg. effect on the enzyme of excessive amounts of acetaldehyde. After optimizing the process, several substrates participated in the reaction and provided the target products in moderate to high yields using this single lipase-catalyzed one-pot biotransformation.

Applied Biochemistry and Biotechnology published new progress about Aldol addition. 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Category: bromides-buliding-blocks.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Kayser, Margaret M. published the artcile< The internal steric push-effect: its consequences on the reactivity of carbonyl functions in 3-substituted phthalic anhydrides>, COA of Formula: C8H3BrO3, the main research area is NMR phthalic anhydride; regioselectivity nucleophilic addition; mol mechanic phthalic anhydride.

The 13C NMR for a number of 3-substituted phthalic anhydrides and corresponding lactones were measured. Substituent effects were discussed. MM2 calculations for several 3-substituted phthalic anhydrides predict that the substituent and the neighboring carbonyl group remain coplanar and within the plane of the aromatic ring. To alleviate the imposed crowding, there is an in-plane distortion of the bond angle of the substituent and the carbonyl function. The observed angle of distortion increases with increasing steric demand of the substituent, in agreement with repulsive van der Waals interaction between those two groups. Diminished reactivity of the ortho carbonyl groups vis-a-vis nucleophiles in 3-substituted phthalic anhydrides may be linked to the internal steric push-effect which causes the displacement of electrons in the CO bond from O to C.

Spectroscopy Letters published new progress about Bond angle. 82-73-5 belongs to class bromides-buliding-blocks, and the molecular formula is C8H3BrO3, COA of Formula: C8H3BrO3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Adolfo Cuesta, Sebastian; Cordova-Sintjago, Tania; Ramon Mora, Jose published the artcile< Sulfonylation of Five-Membered Aromatic Heterocycles Compounds through Nucleophilic Aromatic Substitution: Concerted or Stepwise Mechanism?>, Recommanded Product: Ethyl 5-bromothiophene-2-carboxylate, the main research area is heterocyclic compound sulfonylation nucleophilic aromatic substitution mechanism activation energy.

Heterocyclic sulfones are relevant in medicinal chem., drug design and organic synthesis, and the mechanism of sulfonylation of five-membered heterocycles is not clear. In this work, it is presented a computational study on the mechanism of sulfonylation of five-membered heterocycles compounds Concerted and stepwise mechanisms for the nucleophilic aromatic substitution (SNAr) involved in the reaction were examined Effect of the neighboring group (NG), heteroatom in the ring (HT), nucleophile (NU), and leaving group (LG) in fourteen reactions were examined Anal. of the intrinsic reaction coordinate, reaction force, natural bond orbital (NBO) charges and bond indexes give a reasonable insight about the mechanism for the reactions studied. Results revealed activation free energies ranging from 20.8 kcal/mol up to 38.6 kcal/mol. Reaction force anal. showed that structural changes in the reactant are the most important component associated with the energy of activation with more than 60% of the contribution. Most sulfonylation reactions in this study proceed through a concerted mechanism; only two occur though a stepwise-Meisenheimer-intermediate mechanism.

ChemistrySelect published new progress about Activation energy. 5751-83-7 belongs to class bromides-buliding-blocks, and the molecular formula is C7H7BrO2S, Recommanded Product: Ethyl 5-bromothiophene-2-carboxylate.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Jiang, Jianfeng; Wang, Xia; Liu, Shengping; Zhang, Sichen; Yang, Binmiao; Zhao, Yu; Lu, Shenci published the artcile< Enantioselective Cascade Annulation of α-Amino-ynones and Enals Enabled by Gold and Oxidative NHC Relay Catalysis>, Computed Properties of 3893-18-3, the main research area is pyrrole fused lactone preparation enantioselective; amino ynone enal oxidative tandem cyclization gold catalyst; Cascade Annulation; Cycloaddition; Enantioselectivity; Gold Catalysis; Relay Catalysis.

Unprecedented gold and oxidative NHC relay catalysis enables highly enantioselective cascade annulation between readily available α-amino-ynones R1CCC(O)CH2NHR2 (R1 = H, Ph, 4-fluorophenyl, 3,5-dimethoxyphenyl, etc.; R2 = Boc, Ts, Cbz) with enals R3CH=CHC(O)H (R3 = prop-1-en-1-yl, Ph, 2-thienyl, 2-naphthyl, etc.). This method utilizes the in situ-generated pyrrolin-4-ones as a novel and versatile synthon, which engage with α,β;-unsaturated acylazolium intermediates generated from enals by oxidative NHC catalysis to produce pyrrole-fused lactones I in high yield and excellent enantioselectivity. Synthetic utility of the lactone products is also demonstrated by facile conversion to densely functionalized pyrroles/pyrrolin-4-ones e.g., II in high yields with excellent stereopurity.

Angewandte Chemie, International Edition published new progress about Alkynyl ketones Role: RCT (Reactant), RACT (Reactant or Reagent). 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Computed Properties of 3893-18-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Wang, Hao; Gao, Yuzhen; Zhou, Chunlin; Li, Gang published the artcile< Visible-Light-Driven Reductive Carboarylation of Styrenes with CO2 and Aryl Halides>, Formula: C7H4BrF3, the main research area is photochem regioselective reductive carboarylation styrene carbon dioxide aryl halide.

The first example of visible-light-driven reductive carboarylation of styrenes with CO2 and aryl halides in a regioselective manner has been achieved. A broad range of aryl iodides and bromides were compatible with this reaction. Moreover, pyridyl halides, alkyl halides, and even aryl chlorides were also viable with this method. These findings may stimulate the exploration of novel visible-light-driven Meerwein arylation-addition reactions with user-friendly aryl halides as the radical sources and the photocatalytic utilization of CO2. Thus, e.g., reaction of 1,1-diphenylethylene with PhI and CO2 under blue light in presence of [Ir(ppy)2(dtbbpy)]PF6 photocatalyst and hydrogen atom transfer catalyst DABCO with HCO2K as terminal reductant and K2CO3 as base in DMSO followed by methylation afforded I (82%, 78% isolated).

Journal of the American Chemical Society published new progress about Aryl bromides Role: RCT (Reactant), RACT (Reactant or Reagent). 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Formula: C7H4BrF3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Zhao, Wen-Tao; Lu, Zhuo-Qun; Zheng, Hanliang; Xue, Xiao-Song; Zhao, Dongbing published the artcile< Rhodium-Catalyzed 2-Arylphenol-Derived Six-Membered Silacyclization: Straightforward Access toward Dibenzooxasilines and Silicon-Containing Planar Chiral Metallocenes>, Electric Literature of 81107-97-3, the main research area is rhodium catalyst arylphenol silacyclization stereoselective; benzooxasiloline dibenzooxasiline silicon planar chiral metallocene preparation photophys property; crystal structure mol chiral ferrocene silyl cyclic preparation optimized.

The C/Si switch strategy has been regarded as a useful and efficient strategy for the discovery of drugs and materials. Thus, development of a methodol. to access diverse silacycles is of great significance and in great demand. Among these, C-H bond silylation provides a powerful and straightforward synthetic method to form diverse silacycles in an atom- and step-economical fashion. However, C-H bond silylation has not been used to access any six-membered silicon-bridged π-conjugated scaffolds and enantioselective six-membered C-H silylation has never been presented. Herein, we successfully accessed diverse six-membered π-conjugated dibenzooxasilines via C-H bond silylation and investigated their photophys. properties. Furthermore, we realized enantioselective six-membered C-H silylation to directly afford planar chiral metallocene oxasilolanes with high ee (up to 95% ee). We also demonstrated the synthetic usefulness of dibenzooxasilines and planar chiral metallocene-fused benzooxasilolines as valuable synthetic intermediates via diverse addnl. transformations. Moreover, six-membered silicon-bridged ladder π-conjugated systems were designed and rapidly constructed by using our methods. The “”isomerization”” and “”silicon”” effects on mol. geometries and photophys. properties were also evaluated in detail.

ACS Catalysis published new progress about Chirality. 81107-97-3 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3O, Electric Literature of 81107-97-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Ibrahem, Ismail; Breistein, Palle; Cordova, Armando published the artcile< One-Pot Three-Component Highly Selective Synthesis of Homoallylboronates by Using Metal-Free Catalysis>, Application In Synthesis of 3893-18-3, the main research area is homoallylboronate preparation catalyst imidazolium amine tandem reaction stereoselective; pinacolboron tandem unsaturated aldehyde phosphoranylidene catalyst imidazolium amine stereoselective.

The authors have developed the 1st metal-free 1-pot three-component catalytic selective reaction between a diboron reagent, α,β-unsaturated aldehydes, and 2-(triphenylphosphoranylidene)acetate esters. The multicomponent reactions proceed with high chemo- and regioselectivity through a catalytic β-boration/Wittig sequence, which gives the corresponding homoallylboronates in 59% to 63% yield by using simple bench-stable N-heterocyclic carbenes and amines as catalysts. In addition, a novel merging of the catalytic cycles of NHC nucleophilic activation of diboron reagents and amine-catalyzed iminium activation of enals was disclosed. Further development of this type of 1-pot multicomponent catalytic reactions, enantioselective variants, and its application in total synthesis is ongoing in the authors’ laboratories

Chemistry – A European Journal published new progress about 1,2-Addition reaction. 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Application In Synthesis of 3893-18-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Slack, Rachel D.; Abramyan, Ara M.; Tang, Helen; Meena, Sitaram; Davis, Bruce A.; Bonifazi, Alessandro; Giancola, JoLynn B.; Deschamps, Jeffrey R.; Naing, Sett; Yano, Hideaki; Singh, Satinder K.; Newman, Amy Hauck; Shi, Lei published the artcile< A Novel Bromine-Containing Paroxetine Analogue Provides Mechanistic Clues for Binding Ambiguity at the Central Primary Binding Site of the Serotonin Transporter>, HPLC of Formula: 3893-18-3, the main research area is serotonin transporter paroxetine serotonin reuptake inhibitors SAR asym chem; Paroxetine; asymmetric chemistry; organocatalysis; selective serotonin reuptake inhibitors; serotonin transporter; structure−activity relationship.

The serotonin transporter (SERT) is the primary target for the selective serotonin reuptake inhibitors (SSRIs). However, the structural basis for the extraordinarily high binding affinity of the widely prescribed SSRI, paroxetine, to human SERT (hSERT) has not yet been fully elucidated. Our previous findings unveiled a plausible ambiguity in paroxetine’s binding orientations that may constitute an integral component of this SSRI’s high affinity for hSERT. Herein, we investigate factors contributing to paroxetine’s high affinity by modifying both the ligand and the protein. We generated a series of bromine (Br)-containing derivatives and found that the one in which the 4-F of paroxetine had been replaced with the chem. similar but more electron-rich Br atom (13) had the highest affinity. By comparatively characterizing the binding of paroxetine and 13 to both wild type (WT) and a construct harboring a paroxetine-sensitive mutation in the binding cavity, we identified a mechanistic determinant responsible for the pose ambiguity of paroxetine, which can guide future drug design.

ACS Chemical Neuroscience published new progress about Binding energy (binding affinity). 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, HPLC of Formula: 3893-18-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary