Category: 188813-04-9

Majhi, Jadab; Zhou, Bohang; Zhuang, Yuxin; Tom, Mai-Jan; Dai, Huifang; Evans, P. Andrew published the artcile< Palladium-Catalyzed Cross-Coupling of Cyanohydrins with Aryl Bromides: Construction of Biaryl Ketones>, Name: 3-Bromo-5-methylbenzaldehyde, the main research area is biaryl ketone preparation; cyanohydrin aryl bromide coupling palladium catalyst.

The palladium-catalyzed cross-coupling of the lithium anion of aryl tert-butyldimethylsilyl-protected cyanohydrins Ar1CH(CN)OTBS (Ar1 = C6H5, 4-FC6H4, 3-CH3OC6H4, etc.) with aryl bromides Ar2Br (Ar2 = Ph, 2-cyano-3-methylphenyl, 3-fluoro-4-methoxyphenyl, etc.) followed by in situdeprotection with fluoride ion provides a convenient and versatile approach to biaryl ketones Ar1C(O)Ar2. This protocol represents the first example of a palladium-catalyzed arylation of a cyanohydrin, which functions as an acyl anion equivalent Hence, in contrast to classical cross-coupling reactions, the pronucleophile component is incorporated in the product to permit further functionalization. The synthetic utility of the new method with applications to bioactive biaryl ketones and the construction of a triaryl diketone that has been used to prepare an extended tetrathiafulvalene have been described.

Synthesis published new progress about Aryl bromides Role: RCT (Reactant), RACT (Reactant or Reagent). 188813-04-9 belongs to class bromides-buliding-blocks, and the molecular formula is C8H7BrO, Name: 3-Bromo-5-methylbenzaldehyde.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Yang, Lingyun; Zhang, Jian; Si, Lianghui; Han, Li; Zhang, Bo; Ma, Hui; Xing, Junhao; Zhao, Leilei; Zhou, Jinpei; Zhang, Huibin published the artcile< Synthesis and biological evaluation of GPR40/FFAR1 agonists containing 3,5-dimethylisoxazole>, Reference of 188813-04-9, the main research area is dimethylisoxazolyl benzyloxy fluorophenylpropanoic acid preparation antidiabetic activity SAR; 3,5-Dimethylisoxazole; Diabetes; GPR40 agonist; Oral glucose tolerance test.

GPR40 is an attractive target due to its glucose-stimulated insulin secretion effect with low risk of causing hypoglycemia, which also can be seen from the clin. studies using TAK-875 (fasiglifam). 3,5-Dimethylisoxazolyl-substituted arylmethoxy fluorobenzenepropanoic acids such as I (R = Me, Et, n-Pr, i-Pr, Bu, i-Bu, cyclopropylmethyl, cyclopentyl; R1 = H, Me, F, Cl, CF3, RO; R2 = F, Cl, MeO; R3 = F, R4 = F, Cl, MeO) were prepared as GPR40 agonists; I (R1 = R2 = R3 = H; R4 = Cl) (II) was a GPR40 agonist with an EC50 value of 15.9 nM. Moreover, II reduced glucose excursion to 23.1% in ICR mice and 29.5% in type 2 diabetic C57BL/6 mice at 30 mg/kg and exhibited satisfactory pharmacokinetics profile. Mol. docking studies of I (R1 = R2 = R3 = R4 = H) with GPR40 were conducted to explain the interaction mode of this series. II with robust efficacy in vitro and in vivo constitutes a promising antidiabetic drug candidate.

European Journal of Medicinal Chemistry published new progress about Antidiabetic agents. 188813-04-9 belongs to class bromides-buliding-blocks, and the molecular formula is C8H7BrO, Reference of 188813-04-9.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Shao, Ling-Yan; Xu, Zhi; Wang, Cun-Ying; Fu, Xiao-Pan; Chen, Miao-Miao; Liu, Hong-Wei; Ji, Ya-Fei published the artcile< Palladium-catalyzed direct mono-aroylation of O-arylmethyl and aryl-substituted acetoxime ethers>, Category: bromides-buliding-blocks, the main research area is ketone preparation regioselective; arylmethyl aryl acetoxime ether aromatic aldehyde aroylation palladium catalyst.

An efficient palladium-catalyzed ortho-aroylation of O-arylmethyl and aryl-substituted acetoxime ethers has been developed; this method has high mono-site selectivity and does not require exogenous ligands. Under the direction of a simple exo-acetoxime auxiliary, a broad scope of masked arylmethyl alcs. and phenols as well as various aromatic aldehydes are compatible with this transformation, which probably follows a mechanistic pathway involving a six- or five-membered exo-cyclopalladated intermediate. The strategy can be expediently adopted to prepare synthetically valuable 1H-benzo[d][1,2]oxazines and benzo[d]isoxazoles. The directing group can be easily removed from the products to afford the functionalized diaryl ketones.

Organic & Biomolecular Chemistry published new progress about Aroylation (regioselective). 188813-04-9 belongs to class bromides-buliding-blocks, and the molecular formula is C8H7BrO, Category: bromides-buliding-blocks.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Shao, Ling-Yan; Xu, Zhi; Wang, Cun-Ying; Fu, Xiao-Pan; Chen, Miao-Miao; Liu, Hong-Wei; Ji, Ya-Fei published the artcile< Palladium-catalyzed direct mono-aroylation of O-arylmethyl and aryl-substituted acetoxime ethers>, Category: bromides-buliding-blocks, the main research area is ketone preparation regioselective; arylmethyl aryl acetoxime ether aromatic aldehyde aroylation palladium catalyst.

An efficient palladium-catalyzed ortho-aroylation of O-arylmethyl and aryl-substituted acetoxime ethers has been developed; this method has high mono-site selectivity and does not require exogenous ligands. Under the direction of a simple exo-acetoxime auxiliary, a broad scope of masked arylmethyl alcs. and phenols as well as various aromatic aldehydes are compatible with this transformation, which probably follows a mechanistic pathway involving a six- or five-membered exo-cyclopalladated intermediate. The strategy can be expediently adopted to prepare synthetically valuable 1H-benzo[d][1,2]oxazines and benzo[d]isoxazoles. The directing group can be easily removed from the products to afford the functionalized diaryl ketones.

Organic & Biomolecular Chemistry published new progress about Aroylation (regioselective). 188813-04-9 belongs to class bromides-buliding-blocks, and the molecular formula is C8H7BrO, Category: bromides-buliding-blocks.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Swier, L. J. Y. M.; Monjas, L.; Reessing, F.; Oudshoorn, R. C.; Aisyah; Primke, T.; Bakker, M. M.; van Olst, E.; Ritschel, T.; Faustino, I.; Marrink, S. J.; Hirsch, A. K. H.; Slotboom, D. J. published the artcile< Insight into the complete substrate-binding pocket of ThiT by chemical and genetic mutations>, SDS of cas: 188813-04-9, the main research area is ThiT gene mutation binding pocket Lactococcus.

Energy-coupling factor (ECF) transporters are involved in the uptake of micronutrients in bacteria. The transporters capture the substrate by high-affinity binding proteins, the so-called S-components. Here, we present the anal. of two regions of the substrate-binding pocket of the thiamine-specific S-component in Lactococcus lactis, ThiT. First, interaction of the thiazolium ring of thiamine with residues Trp34, His125 and Glu84 by π-π-stacking and cation-π is studied, and second, the part of the binding pocket that extends from the hydroxyl group. We mutated either the transported ligand (chem.) or the protein (genetically). Surprisingly, modifications in the thiazolium ring by introducing substituents with opposite electronic effects had similar effects on the binding affinity. We hypothesize that the electronic effects are superseeded by steric effects of the added substituents, which renders the study of isolated interactions difficult. Amino acid substitutions in ThiT indicate that the electrostatic interaction facilitated by residue Glu84 of ThiT and thiamine is necessary for picomolar affinity. Deazathiamine derivatives that explore the subpocket of the binding site extending from the hydroxyl group of thiamine bind with high affinity to ThiT and may be developed into selective inhibitors of thiamine transport by ECF transporters. Mol.-dynamics simulations suggest that two of these derivatives may not only bind to ThiT, but could also be transported.

MedChemComm published new progress about Electrostatic force. 188813-04-9 belongs to class bromides-buliding-blocks, and the molecular formula is C8H7BrO, SDS of cas: 188813-04-9.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Li, Jian-Yuan; Miklossy, Gabriella; Modukuri, Ram K.; Bohren, Kurt M.; Yu, Zhifeng; Palaniappan, Murugesan; Faver, John C.; Riehle, Kevin; Matzuk, Martin M.; Simmons, Nicholas published the artcile< Palladium-Catalyzed Hydroxycarbonylation of (Hetero)aryl Halides for DNA-Encoded Chemical Library Synthesis>, Quality Control of 188813-04-9, the main research area is palladium catalyzed hydroxycarbonylation heteroaryl halide DNA encoded library synthesis.

A strategy for DNA-compatible, palladium-catalyzed hydroxycarbonylation of (hetero)aryl halides on DNA-chem. conjugates has been developed. This method generally provided the corresponding carboxylic acids in moderate to very good conversions for (hetero)aryl iodides and bromides, and in poor to moderate conversions for (hetero)aryl chlorides. These conditions were further validated by application within a DNA-encoded chem. library synthesis and subsequent discovery of enriched features from the library in selection experiments against two protein targets.

Bioconjugate Chemistry published new progress about Carbonylation. 188813-04-9 belongs to class bromides-buliding-blocks, and the molecular formula is C8H7BrO, Quality Control of 188813-04-9.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Yeh, Chien-Hung; Chen, Wei-Chen; Gandeepan, Parthasarathy; Hong, Ya-Chun; Shih, Cheng-Hung; Cheng, Chien-Hong published the artcile< RhIII-catalyzed dual directing group assisted sterically hindered C-H bond activation: a unique route to meta and ortho substituted benzofurans>, Synthetic Route of 188813-04-9, the main research area is internal alkyne hydroxyphenyloxime ether regioselective CH activation heterocyclization rhodium; benzofuran regioselective directing group assisted preparation mol crystal structure; rhodium regioselective sterically hindered CH activation heterocyclization catalyst.

A new strategy for the synthesis of highly substituted benzofurans, e.g., I (X-rays single crystal structure shown), from meta-substituted hydroxybenzenes and alkynes via a rhodium(III)-catalyzed activation of a sterically hindered C-H bond is demonstrated. A possible mechanism involving dual directing group assisted ortho C-H bond activation is proposed.

Organic & Biomolecular Chemistry published new progress about Alkynes, internal Role: RCT (Reactant), RACT (Reactant or Reagent). 188813-04-9 belongs to class bromides-buliding-blocks, and the molecular formula is C8H7BrO, Synthetic Route of 188813-04-9.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Li, Zhong-Yuan; Lakmal, Hetti Handi Chaminda; Qian, Xiaolin; Zhu, Zhenyu; Donnadieu, Bruno; McClain, Sarah J.; Xu, Xue; Cui, Xin published the artcile< Ruthenium-Catalyzed Enantioselective C-H Functionalization: A Practical Access to Optically Active Indoline Derivatives>, Application In Synthesis of 188813-04-9, the main research area is hydroindolecarboxaldehyde regioselective enantioselective preparation; ruthenium catalyst enantioselective cyclization alkenylaminobenzaldehyde transient imine directing group; study mechanism ruthenium catalyzed directed enantioselective cyclization alkenylaminobenzaldehyde.

In the presence of [Ru(p-cymene)Cl2]2, nonracemic 1-(1-naphthyl)ethylamine as a transient directing group, and N-phthaloyl-L-tert-leucine, 3-(alkenylamino)benzaldehydes such as I underwent enantioselective cyclization mediated by AgBF4 and KH2PO4 in chlorobenzene/hexafluoroisopropanol to yield nonracemic dihydroindolecarboxaldehydes such as II in up to 92% yield with 96% ee. A benzindolecarboxaldehyde potentially useful for the synthesis of lysergic acid analogs was prepared using this method. The reaction mechanism was studied using the preparation of ruthenacycles related to potential reaction intermediates, mass spectrometric detection of reaction intermediates, and deuterium labeling experiments

Journal of the American Chemical Society published new progress about Benzaldehydes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (m-alkenylamino). 188813-04-9 belongs to class bromides-buliding-blocks, and the molecular formula is C8H7BrO, Application In Synthesis of 188813-04-9.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Xing, Qiaoyan; Xiao, Fuhong; Mao, Guojiang; Deng, Guo-Jun published the artcile< A Four-Component Reaction for the Synthesis of Thienopyrrolediones under Transition Metal Free Conditions>, Related Products of 188813-04-9, the main research area is thienopyrrole dione preparation green chem; aldehyde ketoamide multicomponent reaction.

A three-starting-material four-component reaction strategy is described to construct thienopyrrolediones (TPDs) I (R = H, Me, Et, Ph, Cy; R1 = Ph, naphthalen-2-yl, furan-2-yl, quinolin-8-yl, etc.; R2 = Ph, 4-(benzyloxy)phenyl, thiophen-2-yl, pyridin-3-yl, etc.) from the simplest raw materials, elemental sulfur, aldehydes R1CHO and R2CHO, and β-ketoamides e.g., 1-methylpyrrolidin-2-one, under transition metal free conditions. Compared with traditional multistep reaction sequences, this process is simple, efficient, environmentally friendly, and atom-economic and has laid the foundation for further development of an easily synthesized TPD unit.

Organic Letters published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 188813-04-9 belongs to class bromides-buliding-blocks, and the molecular formula is C8H7BrO, Related Products of 188813-04-9.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

He, Zhi-Tao; Zhao, Yi-Shuang; Tian, Ping; Wang, Chuan-Chuan; Dong, Han-Qing; Lin, Guo-Qiang published the artcile< Copper-Catalyzed Asymmetric Hydroboration of α-Dehydroamino Acid Derivatives: Facile Synthesis of Chiral β-Hydroxy-α-amino Acids>, Category: bromides-buliding-blocks, the main research area is dehydroamino acid preparation asym hydroboration copper catalyst; hydroxy amino acid asym preparation.

The Cu-catalyzed asym. conjugate hydroboration reaction of β-substituted α-dehydroamino acid derivatives has been established, affording enantio-enriched syn- and anti-β-boronate-α-amino acid derivatives with excellent combined yields (83-99%, dr ≈ 1:1) and excellent enantioselectivities (92-98% ee). The hydroboration products were expediently converted into valuable β-hydroxy-α-amino acid derivatives, which were widely used in the preparation of chiral drugs and bioactive mols.

Organic Letters published new progress about Amino acids, hydroxy Role: SPN (Synthetic Preparation), PREP (Preparation). 188813-04-9 belongs to class bromides-buliding-blocks, and the molecular formula is C8H7BrO, Category: bromides-buliding-blocks.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary