Tag: M.W=200-250

Fu, Zhenqian; Sun, Hui; Chen, Shaojin; Tiwari, Bhoopendra; Li, Guohui; Robin Chi, Yonggui published the artcile< Controlled β-protonation and [4+2] cycloaddition of enals and chalcones via N-heterocyclic carbene/acid catalysis: toward substrate independent reaction control>, Recommanded Product: 3-(4-Bromophenyl)acrylaldehyde, the main research area is enol lactone preparation enal chalcone cycloaddition NHC catalyst.

A substrate-independent selective generation of enolates over homoenolate equivalent in NHC-catalyzed reactions of enals and chalcones is disclosed. Acid co-catalysts play vital roles in control of the reaction pathways, allowing for individual access to diverse products from identical substrates.

Chemical Communications (Cambridge, United Kingdom) published new progress about [4+2] Cycloaddition reaction. 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Recommanded Product: 3-(4-Bromophenyl)acrylaldehyde.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Tang, Shibing; He, Jinmei; Sun, Yongquan; He, Liuer; She, Xuegong published the artcile< Efficient and Regioselective One-Pot Synthesis of 3-Substituted and 3,5-Disubstituted Isoxazoles>, Electric Literature of 3893-18-3, the main research area is isoxazole regioselective preparation; hydroxyl toluenesulfonamide unsaturated aldehyde ketone conjugate addition cyclization.

A series of 3-substituted and 3,5-disubstituted isoxazoles have been efficiently synthesized in moderate to excellent yields by the reaction of N-hydroxyl-4-toluenesulfonamide with α,β-unsaturated aldehydes/ketones. This novel strategy is associated with readily available starting materials, mild conditions, high regioselectivity, and wide scope.

Organic Letters published new progress about Conjugate addition reaction. 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Electric Literature of 3893-18-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Li, Xuejing; Deng, Xingwang; Coyne, Anthony G.; Srinivasan, Rajavel published the artcile< meta-Nitration of Arenes Bearing ortho/para Directing Group(s) Using C-H Borylation>, Related Products of 401-78-5, the main research area is meta nitroarene regioselective preparation; arene borylation nitration tandem iridium catalyst copper; C−H borylation; copper catalysis; nitration; nitro(hetero)arenes; one-pot reactions.

The meta-nitration of arenes bearing ortho/para directing group(s) using the iridium-catalyzed C-H borylation reaction followed by a newly developed copper(II)-catalyzed transformation of the crude aryl pinacol boronate esters into the corresponding nitroarenes RNO2 [R = 4,5-di-ClC6H3, 3,4-di-BrC6H3, 5-Cl-3-pyridyl, etc.] in a one-pot fashion was reported. The reaction tolerated a wide array of ortho/para-directing groups, such as -F, -Cl, -Br, -CH3, -Et, -iPr -OCH3 and -OCF3. It also provided regioselective access to the nitro derivatives of π-electron-deficient heterocycles, such as pyridine and quinoline derivatives The application of this method was demonstrated in the late-stage modification of complex mols. and also in the gram-scale preparation of an intermediate en route to the FDA-approved drug Nilotinib. Finally, showed that the nitro product obtained by this strategy could also be directly converted to the aniline or hindered amine through Baran’s amination protocol.

Chemistry – A European Journal published new progress about Aromatic compounds Role: RCT (Reactant), RACT (Reactant or Reagent). 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Related Products of 401-78-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Zhou, Jie; Bie, Jianbo; Wang, Xiaoyu; Liu, Quan; Li, Rongcui; Chen, Hualong; Hu, Jinping; Cao, Hui; Ji, Wenming; Li, Yan; Liu, Shuainan; Shen, Zhufang; Xu, Bailing published the artcile< Discovery of N-Arylsulfonyl-Indole-2-Carboxamide Derivatives as Potent, Selective, and Orally Bioavailable Fructose-1,6-Bisphosphatase Inhibitors-Design, Synthesis, In Vivo Glucose Lowering Effects, and X-ray Crystal Complex Analysis>, Related Products of 89003-95-2, the main research area is T2MD liver FBPase inhibitors glucose lowering crystal structure binding.

Liver fructose-1,6-bisphosphatase (FBPase) is a key enzyme in the gluconeogenesis pathway. Inhibiting FBPase activity represents a potential treatment for type 2 diabetes mellitus. A series of novel N-arylsulfonyl-4-arylamino-indole-2-carboxamide derivatives have been disclosed as FBPase inhibitors. Through extensive structure-activity relationship investigations, a promising candidate mol. Cpd118 [sodium (7-chloro-4-((3-methoxyphenyl)amino)-1-methyl-1H-indole-2-carbonyl] [(4-methoxyphenyl)sulfonyl)amide](I) has been identified with high inhibitory activity against human liver FBPase (IC50, 0.029 ± 0.006 μM) and high selectivity relative to the other six AMP-binding enzymes. Importantly, Cpd118 produced significant glucose-lowering effects on both type 2 diabetic KKAy mice and ZDF rats as demonstrated by substantial reductions in the fasting and postprandial blood glucose levels, as well as the HbA1c level. Furthermore, Cpd118 elicited a favorable pharmacokinetic profile with an oral bioavailability of 99.1%. Moreover, the X-ray crystal structure of the Cpd118-FBPase complex was resolved, which revealed a unique binding mode and provided a structural basis for its high potency and selectivity.

Journal of Medicinal Chemistry published new progress about Bioavailability. 89003-95-2 belongs to class bromides-buliding-blocks, and the molecular formula is C8H4BrNO, Related Products of 89003-95-2.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Miao, Shi-Xing; Wan, Lin-Xi; He, Zhen-Xiang; Zhou, Xian-Li; Li, Xiaohuan; Gao, Feng published the artcile< Pd-Catalyzed Direct Diversification of Natural Anti-Alzheimer's Disease Drug: Synthesis and Biological Evaluation of N-Aryl Huperzine A Analogues>, Computed Properties of 401-78-5, the main research area is aryl huperzine preparation anti Alzheimer activity acetylcholinesterase SAR chemoselective; huperzine aryl bromide Buchwald Hartwig coupling palladium catalyst.

The first systematic direct diversification of a complex natural product by metal-catalyzed N-H functionalization was carried out. A new series of N-(hetero)aryl analogs I (Ar = Ph, 2-naphthyl, 4-methylpyridin-2-yl, etc.) of the natural anti-Alzheimer’s disease drug huperzine A (HPA) was prepared via palladium-catalyzed Buchwald-Hartwig cross-coupling reactions of HPA with various aryl bromides ArBr in good yields. Most of the N-aryl-huperzine A (N-aryl-HPA) analogs showed good acetylcholinesterase (AChE) inhibitory activity in in vitro experiments Three arylated huperzine A analogs I (Ar = 4-FC6H4, 4-methoxy-2,6-dimethylphenyl, 5-methoxypyridin-2-yl) exhibited stronger anti-AChE activity than HPA. The 5-methoxy-2-pyridyl analog I (Ar = 5-methoxypyridin-2-yl) displayed the most potent AChE inhibition activity, with an IC50 value of 1.5μM, which was 7.6-fold more active than HPA. Compound I (Ar = 5-methoxypyridin-2-yl) also exhibited better neuroprotective activity for H2O2-induced damage in SH-SY5Y cells than HPA. Structure-activity relationship anal. suggested that the electron d. of the installed aromatic ring or heteroaromatic ring played a significant role in inducing the AChE inhibition activity. Overall, compound I (Ar = 5-methoxypyridin-2-yl) showed the advantages of easy synthesis, high potency and selectivity, and improved neuroprotection, making it a potential huperzine-type lead compound for Alzheimer’s disease drug development.

Journal of Natural Products published new progress about Alzheimer disease. 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Computed Properties of 401-78-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Chen, Lian-Mei; Zhou, Chuang; Li, Jing; Li, Jun; Guo, Xiao-Qiang; Kang, Tai-Ran published the artcile< Copper-catalyzed reactions of α,β-unsaturated N-tosylhydrazones with diaryliodonium salts to construct N-arylpyrazoles and diaryl sulfones>, Name: 3-(4-Bromophenyl)acrylaldehyde, the main research area is propenyl tosylhydrazone diaryliiodonium triflate copper catalyst tandem heterocyclization Ullman; arylpyrazole diarylsulfone preparation regioselective.

An economical copper-catalyzed reaction of α,β-unsaturated N-tosylhydrazones with diaryliodonium salts to construct both N-arylpyrazoles and diaryl sulfones was developed. Both the p-toluenesulfonyl anion and the 3-arylpyrazole intermediates were formed in-situ from N-tosylhydrazones. Subsequently, the former reacted rapidly with diaryliodonium salts to give diaryl sulfones and aryl iodide intermediates and the latter reacted with aryl iodide to give N-arylpyrazoles under copper-catalyzed conditions. Using unsym. mesityl phenyliodonium salts as substrates, mesityl p-toluenesulfide was obtained as the major product. This reaction took full advantage of the “”waste”” part of substrates to form an extra diaryl sulfone.

Organic & Biomolecular Chemistry published new progress about Aromatic compounds, sulfones Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Name: 3-(4-Bromophenyl)acrylaldehyde.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Moschona, Fotini; Misirlaki, Christina; Karadimas, Nikolaos; Koutiva, Maria; Savvopoulou, Ioanna; Rassias, Gerasimos published the artcile< Organocatalytic Asymmetric Halocyclization of Allylic Amides to Chiral Oxazolines Using DTBM-SEGPHOS-Mechanistic Implications from Hammett Plots>, Name: 3-Bromobenzotrifluoride, the main research area is oxazoline preparation enantioselective regioselective; allylic amide chlorocyclization chiral diphosphine organocatalyst.

The intramol. halocyclization of alkenes possessing an internal heteroatom nucleophile leads to multifunctional heterocycles which are useful versatile intermediates in organic synthesis. The asym. chlorocyclization of 2-substituted allylic amides ArC(O)NHCH2C(=CH2)R (R = Ph, 4-FC6H4, pyridin-3-yl, naphthalen-1-yl, etc.; Ar = Ph, 4-MeOC6H4, 4-MeC6H4, etc.) gives access to chiral oxazolines I (X = Cl) bearing a chloromethyl moiety for further synthetic manipulation. The literature reports on this transformation involve complex syntheses of the 2-substituted allylic amides and cryogenic temperatures for achieving high enantioselectivities in the organocatalyzed halocyclization step. Based on the Heck reaction of aryl bromides ArBr (Ar = Ph, 4-CNC6H4, pyridin-3-yl, naphthalen-1-yl, etc.;) and Boc-protected allylamine or allylamine benzamides, a practical synthesis of 2-substituted allylic amides that does not require chromatog. was developed and accomplished their asym. halocyclization reaction with 24-92%ee under practical conditions (5°C, CpME) catalyzed by (S)-(+)-DTBM-SEGPHOS. In addition, using appropriately substituted substrates, Hammett plots were generated and formulated a consistent mechanism for the halocyclization reaction which involves two competing modes of formation of the haliranium intermediate whose relative kinetics are governed by the electronic properties of the substrate.

Symmetry published new progress about Aromatic amines Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Name: 3-Bromobenzotrifluoride.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Eberson, L.; Welinder, H. published the artcile< Cyclic anhydrides. III. Equilibrium constants for the acid-anhydride equilibrium in aqueous solutions of certain vicinal diacids>, Safety of 4-Bromoisobenzofuran-1,3-dione, the main research area is cyclic anhydrides equilibrium constant; acid anhydride equilibrium; vicinal diacids anhydrides equilibrium; succinic acid anhydrides equilibrium; alicyclic acid anhydrides equilibrium; maleic acid anhydrides equilibrium; phthalic acid anhydrides equilibrium.

Equilibrium constant were measured for the equilibrium diacid ⇌ anhydride + H2O in aqueous solutions of a number of vicinal diacids, chosen to correspond to relatively stable or very stable anhydrides. Such acids include di-, tri-, and tetraalkylsuccinic acids, certain alicyclic diacids, dialkylmaleic acids, and some alkyl-substituted phthalic acids. In all cases, the driving force for formation of a stable anhydride is relief of steric strain in the anhydride as compared to the corresponding diacid. Diisopropylmaleic anhydride was prepared as a new compound Low–melting 2,3-diethyl-2,3-dimethylsuccinic acid was shown to possess the dl-configuration by resolution.

Journal of the American Chemical Society published new progress about Anhydrides Role: PRP (Properties). 82-73-5 belongs to class bromides-buliding-blocks, and the molecular formula is C8H3BrO3, Safety of 4-Bromoisobenzofuran-1,3-dione.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Niu, Zhiqiang; He, Xinwei; Shang, Yongjia published the artcile< The efficient enantioselective synthesis of dihydropyrans via organocatalytic Michael addition reactions>, Product Details of C9H7BrO, the main research area is dihydropyran enantioselective preparation; cyanoketone alkenal enantioselective Michael addition organocatalyst.

An asym. Michael addition of α-cyanoketones to α,β-unsaturated aldehydes to form chiral dihydropyrans catalyzed by L-diphenylprolinol trimethylsilyl ether is presented. A series of 3,4-dihydropyrans were obtained in excellent yields (up to 91%) and enantioselectivities (up to 98% ee). A plausible mechanism for this process is proposed.

Tetrahedron: Asymmetry published new progress about Alkenals Role: RCT (Reactant), RACT (Reactant or Reagent). 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Product Details of C9H7BrO.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Zheng, Kewang; Xiao, Guanlin; Guo, Tao; Ding, Yalan; Wang, Chengdong; Loh, Teck-Peng; Wu, Xiaojin published the artcile< Intermolecular Reductive Heck Reaction of Unactivated Aliphatic Alkenes with Organohalides>, HPLC of Formula: 3480-11-3, the main research area is aryl carboxamide regioselective preparation; alkene organohalide reductive Hexk reaction palladium catalyst.

A general intermol. reductive Heck reaction of organohalides with both terminal and internal unactivated aliphatic alkenes has been first realized in high yield with complete anti-Markovnikov selectivity. The challenging vinyl bromides, aryl chlorides, and polysubstituted internal alkenes were first applied. More than 100 remote carbofunctionalized alkyl carboxylic acid derivatives were rapidly synthesized from easily accessible starting materials. The synthesis of drug mols. has further demonstrated the wide synthetic utility of this scalable strategy. Preliminary mechanistic studies are consistent with the proposed catalytic cycle.

Organic Letters published new progress about Alkenes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 3480-11-3 belongs to class bromides-buliding-blocks, and the molecular formula is C8H5BrS2, HPLC of Formula: 3480-11-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary