Tag: M.W=200-250

Canceill, Josette; Collet, Andre published the artcile< Synthesis and optical activity of p-(-)-2,7,12-tribromo-3,8,13-trihydroxycyclotribenzylene and related compounds. Evidence for the non-orthogonality of the B2u and B1u transitions in polysubstituted benzenes and its relevance to the exciton chirality method>, COA of Formula: C8H9BrO2, the main research area is cyclotribenzylene tribromotrihydroxy preparation configuration; trimerization cyclo benzenemethanol; benzenemethanol cyclotrimerization.

Cyclotrimerization of 4,3-Br(MeO)C6H3CH2OH gave 2,7,12-tribromo-3,8,13-trimethoxycyclotribenzylene (I, R = Me) and demethylation of the latter gave triphenol (±)-I (R = H) which was resolved into enantiomers. Methylation and acetylation of (+)- or (-)-I (R = H) furnished (+)- or (-)-I (R = Me, Ac). (-)-I were assigned P-(-) absolute configuration by chem. correlation with M-(+)-cyclotrianisylene. The optical activity of I was analyzed in the light of the exciton theory. In all compounds the exptl. exciton CD pattern in the 230 nm region, the B1u transition, was opposite to that expected from the spectroscopic moments of the substituents. This unexpected behavior suggested that the angle between the polarization directions of the B2u (290 nm) and B1u (230 nm) transitions in I should significantly depart from the value, 90°, usually assumed in polysubstituted benzenes, and emphasized the risk of using the B1u transition for configurational assignments based on chiroptical methods.

Nouveau Journal de Chimie published new progress about Absolute configuration. 17100-64-0 belongs to class ethers-buliding-blocks, and the molecular formula is C8H9BrO2, COA of Formula: C8H9BrO2.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Vekariya, Rakesh H.; Lei, Wei; Ray, Abhisek; Saini, Surendra K.; Zhang, Sixue; Molnar, Gabriella; Barlow, Deborah; Karlage, Kelly L.; Bilsky, Edward J.; Houseknecht, Karen L.; Largent-Milnes, Tally M.; Streicher, John M.; Ananthan, Subramaniam published the artcile< Synthesis and Structure-Activity Relationships of 5'-Aryl-14-alkoxypyridomorphinans: Identification of a μ Opioid Receptor Agonist/δ Opioid Receptor Antagonist Ligand with Systemic Antinociceptive Activity and Diminished Opioid Side Effects>, Reference of 190788-60-4, the main research area is MOR agonist DOR antagonist antinociceptive SAR side effects.

We previously identified a pyridomorphinan (6, SRI-22138) possessing a 4-chlorophenyl substituent at the 5′-position on the pyridine and a 3-phenylpropoxy at the 14-position of the morphinan as a mixed μ opioid receptor (MOR) agonist and δ/κ opioid receptor (DOR/KOR) antagonist with potent antinociceptive activity and diminished tolerance and dependence in rodents. Structural variations at the 5′- and 14-positions of this mol. gave insights into the structure-activity relationships for binding and functional activity. Subtle structural changes exerted significant influence, particularly on the ability of the compounds to function as agonists at the MOR. In vivo evaluation identified compound 20(I) (SRI-39067) as a MOR agonist/DOR antagonist that produced systemically active potent antinociceptive activity in tail-flick assay in mice, with diminished tolerance, dependence/withdrawal, reward liability, and respiratory depression vs. morphine. These results support the hypothesis that mixed MOR agonist/DOR antagonist ligands may emerge as novel opioid analgesics with reduced side effects.

Journal of Medicinal Chemistry published new progress about Analgesics. 190788-60-4 belongs to class ethers-buliding-blocks, and the molecular formula is C13H19BO3, Reference of 190788-60-4.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Liu, Xiaojie; Xu, Biping; Su, Weiping published the artcile< Ni-Catalyzed Deoxygenative Borylation of Phenols Via O-Phenyl-uronium Activation>, Formula: C13H19BO3, the main research area is aryl boronic ester preparation; crystal structure mol nickel intermediate complex diphosphine aryl fluoro; nickel catalyst deoxygenative borylation phenol phenyl uronium activation bond.

Herein, we report an efficient method for the Ni-catalyzed deoxygenative borylation of unprotected phenols and also demonstrate that this Ni-catalyzed phenolic C(sp2)-O transformation is applicable to the Suzuki-Miyaura-type and Heck-type cross-couplings of phenols. Investigations on the reaction intermediate have revealed that the achievement of general, mild deoxygenative cross-coupling reactions of phenols is ascribed to the conversion of phenols into the unusual O-phenyl-uroniums that feature active phenolic C(sp2)-O bonds. The Ni-complex intermediate resulting from an oxidative addition of a phenolic C(sp2)-O bond to monophosphine-supported Ni(0) catalyst was characterized and confirmed to be (PCy3)2Ni(Ar)(F) complex, offering exptl. evidence for the generally proposed C(sp2)-O oxidative addition step.

ACS Catalysis published new progress about Bond activation. 190788-60-4 belongs to class ethers-buliding-blocks, and the molecular formula is C13H19BO3, Formula: C13H19BO3.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Xi, Junwei; Gu, Zhenhua published the artcile< Palladium-Catalzyed Atroposelective 16-Membered Macrocyclization: Total Synthesis of Isoplagiochin D†l>, Synthetic Route of 17100-64-0, the main research area is isoplagiochin D total synthesis atroposelective macrocyclization palladium catalyst WingPhos.

Isoplagiochin D (I) is a ring-strained macrocyclic bisbibenzyl, which shows stable axial chirality in one biaryl structure, and semistable axial chirality in the other biaryl moiety. We report here an unprecedented example for the catalytically asym. synthesis of ring-strained atropisomers via Pd-catalyzed macrocyclization between benzyl halides and carbenes. This newly developed Pd-catalyzed asym. macrocyclization protocol enabled a quick synthesis of isoplagiochin D in a highly enantioselective manner.

Chinese Journal of Chemistry published new progress about Benzyl halides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 17100-64-0 belongs to class ethers-buliding-blocks, and the molecular formula is C8H9BrO2, Synthetic Route of 17100-64-0.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Huang, Chen; Feng, Jie; Ma, Rui; Fang, Shuaishuai; Lu, Tao; Tang, Weifang; Du, Ding; Gao, Jian published the artcile< Redox-Neutral Borylation of Aryl Sulfonium Salts via C-S Activation Enabled by Light>, Computed Properties of 190788-60-4, the main research area is aryl sulfonium salt preparation photochem redox neutral borylation pinacolatodiboron; arylboronate ester preparation; methyl aryl thioether methylation methyl triflate.

Reported here is a novel photoinduced strategy for the borylation of aryl sulfonium salts using bis(pinacolato)diboron as the B source. This method exploits redox-neutral aryl sulfoniums to gain access to aryl radicals via C-S bond activation upon photoexcitation under transition-metal-free conditions. Therefore, it grants access to diverse arylboronate esters with good performance from easily available aryl sulfoniums accompanied by mild conditions, operational simplicity, and easy scalability.

Organic Letters published new progress about Boranes Role: SPN (Synthetic Preparation), PREP (Preparation) (arylboronate esters). 190788-60-4 belongs to class ethers-buliding-blocks, and the molecular formula is C13H19BO3, Computed Properties of 190788-60-4.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Lamola, Jairus L.; Moshapo, Paseka T.; Holzapfel, Cedric W.; Christopher Maumela, Munaka published the artcile< Palladium-catalyzed borylation of aryl bromides and chlorides using phosphatrioxa-adamantane ligands>, Electric Literature of 190788-60-4, the main research area is palladium catalyst borylation aryl bromide chloride phosphatrioxa adamantane; aryl boronate ester preparation.

Catalysts based on the combination of Pd(OAc)2 and the electron-deficient phosphatrioxa-adamantane ligands are described for borylation of aryl bromides and chlorides. Catalytic evaluation of a small library of phosphatrioxa-adamantane ligands provided some insights on the preferred ligand steric profile for borylation reactions. The corresponding aryl boronate esters were accessed under mild conditions (25-70°) and isolated in high yields (up to 96%).

Tetrahedron Letters published new progress about Adamantanes Role: CAT (Catalyst Use), USES (Uses) (phosphatrioxa-). 190788-60-4 belongs to class ethers-buliding-blocks, and the molecular formula is C13H19BO3, Electric Literature of 190788-60-4.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Xie, Qiqiang; Dong, Guangbin published the artcile< Programmable Ether Synthesis Enabled by Oxa-Matteson Reaction>, Recommanded Product: 2-(2-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, the main research area is boronate alkyl aryl oxa Matteson oxygen carbenoid insertion reaction; boron substituted ether product preparation.

The Matteson-type reactions have received increasing interest in constructing complex organic mols. via iterative synthetic strategies; however, the current tactics are almost exclusively based on homologation of pure C chains. Here, the authors report the development of the oxa-Matteson reaction that enables sequential O and carbenoid insertions into diverse alkyl- and arylboronates. It offers a distinct entry to a wide range of B-substituted ethers. The utilities of this method are demonstrated in the preparation of various functional ethers, the asym. synthesis of an acetyl-CoA-carboxylase inhibitor, and the programmable construction of polyethers.

Journal of the American Chemical Society published new progress about Boronic acids, esters Role: RCT (Reactant), RACT (Reactant or Reagent) (alkyl and aryl). 190788-60-4 belongs to class ethers-buliding-blocks, and the molecular formula is C13H19BO3, Recommanded Product: 2-(2-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Xu, Hai-Feng; Pan, You-Lu; Li, Gang-Jian; Hu, Xu-Yang; Chen, Jian-Zhong published the artcile< Copper(II)-Catalyzed Direct C-H (Hetero)arylation at the C3 Position of Indoles Assisted by a Removable N,N-Bidentate Auxiliary Moiety>, Category: ethers-buliding-blocks, the main research area is arylated indole regioselective preparation; indole arylboronic ester arylation copper catalyst.

The regioselective arylation of inert C3-H bonds in indoles reacting with arylboronates via effective copper-mediated catalysis with the aid of a facile and removable 2-pyridinylisopropyl (PIP) group without ligand participation was reported. This newly established method features high compatibility with diverse functional groups between coupling partners, including both indole substrates and arylboron reagents, consequentially leading to operational simplicity and providing access to generate the desired arylated products I [R = H, 4-Me, 5-MeO, 6-Br, etc.; R1 = Me, Bn; Ar = Ph, 2-thienyl, 3-pyridyl, etc.] in good to excellent yields of up to 97%. Synthetically, the PIP-derived amide moiety could subsequently be readily removed under mild reaction conditions to produce useful indolecarboxylic acids for further transformation.

Journal of Organic Chemistry published new progress about Amides, secondary Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 190788-60-4 belongs to class ethers-buliding-blocks, and the molecular formula is C13H19BO3, Category: ethers-buliding-blocks.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Zhang, Qin; Zhong, Ying; Yan, Lin-Na; Sun, Xun; Gong, Tao; Zhang, Zhi-Rong published the artcile< Synthesis and preliminary evaluation of curcumin analogues as cytotoxic agents>, Synthetic Route of 17100-64-0, the main research area is curcumin derivative preparation SAR anticancer cytotoxicity.

A series of curcumin analogs with different substituents at the 4-position of the Ph group were synthesized and screened for in vitro cytotoxicity against a panel of human cancer cell lines. Several novel curcumin analogs, especially I and II, exhibited selective and potent cytotoxic activity against human epidermoid carcinoma cell line A-431 and human glioblastoma cell line U-251, implying their specific potential in the chemoprevention and chemotherapy of skin cancer and glioma. The preliminary SAR information extracted from the results suggested that introduction of appropriate substituents to the 4′-positions could be a promising approach for the development of new cytotoxic curcumin analogs with special selectivity for A-431 and U-251 cell lines.

Bioorganic & Medicinal Chemistry Letters published new progress about Antitumor agents. 17100-64-0 belongs to class ethers-buliding-blocks, and the molecular formula is C8H9BrO2, Synthetic Route of 17100-64-0.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Leubner, Sebastian; Zhao, Haishuang; Van Velthoven, Niels; Henrion, Mickael; Reinsch, Helge; De Vos, Dirk E.; Kolb, Ute; Stock, Norbert published the artcile< Expanding the Variety of Zirconium-based Inorganic Building Units for Metal-Organic Frameworks>, Electric Literature of 190788-60-4, the main research area is zirconium benzenedicarboxylate acetate MOF preparation stability arene borylation catalyst; crystal structure zirconium benzenedicarboxylate biphenyldicarboxylate acetate microporous MOF; Direct C−H borylation; Electron Diffraction; Green Chemistry; Metal-organic Frameworks; Zirconium.

Two new Zr-based metal-organic frameworks [Zr6O4(OH)4(OAc)6(BDC)3] (CAU-26) and [Zr5O4(OH)4(OAc)4(BDC)2] (CAU-27) are reported, which were synthesized from HOAc, a rarely used but green and sustainable solvent (BDC2-: 1,4-benzenedicarboxylate). Structure determination aided by automated electron diffraction tomog. revealed that CAU-26 [Zr6O4(OH)4(OAc)6(BDC)3] is composed of layers of known {Zr6O8} clusters interconnected by terephthalate ions. In contrast CAU-27 [Zr5O4(OH)4(OAc)4(BDC)2] exhibits a three-dimensional structure with a so far unknown type of 1-dimensional inorganic building unit (IBU), which can be rationalized as condensed polyhedron-sharing chains of {Zr6O8} clusters. CAU-26 occurs as an intermediate of the CAU-27 synthesis and can be isolated easily, when reaction temperature and time are decreased. The authors were also able to synthesize two isoreticular derivatives of CAU-27 with extended linker mols. by implementing 4,4′-biphenyldicarboxylic acid (H2BPDC) and 5,5′-dicarboxy-2,2′-bipyridine (H2BIPY). All materials show high thermal and chem. stability as well as permanent microporosity. The excellent stability of CAU-27-BIPY was exploited to synthesize an Ir-supported heterogeneous MOF-based catalyst for the direct C-H borylation of arenes.

Angewandte Chemie, International Edition published new progress about Aromatic hydrocarbons Role: RCT (Reactant), RACT (Reactant or Reagent). 190788-60-4 belongs to class ethers-buliding-blocks, and the molecular formula is C13H19BO3, Electric Literature of 190788-60-4.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem