Month: October 2022

Ting, Chi P.; Tschanen, Esther; Jang, Esther; Maimone, Thomas J. published the artcile< Total synthesis of podophyllotoxin and select analog designs via C-H activation>, Name: Methyl 5-iodothiophene-2-carboxylate, the main research area is podophyllotoxin analog synthesis arylation.

An account of our previously disclosed total synthesis of the aryltetralin lignan natural product podophyllotoxin, a building block used in the synthesis of the FDA-approved anticancer drug etoposide, is disclosed. A C-H activation disconnection was viewed as being amenable to the preparation of E-ring modified analogs but proved challenging to execute. Various insights into palladium-catalyzed C-H arylation reactions on complex scaffolds are reported ultimately leading to the implementation of this strategy and the synthesis of compounds inaccessible by semisynthetic means.

Tetrahedron published new progress about Arylation. 88105-22-0 belongs to class iodides-buliding-blocks, and the molecular formula is C6H5IO2S, Name: Methyl 5-iodothiophene-2-carboxylate.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Gronowitz, Salo; Vilks, Vija published the artcile< Iodo thiophenes and bithienyls>, Product Details of C6H5IO2S, the main research area is .

Iodo thiophenes could be prepared by the reaction of thiophene with iodine and HIO3 to give 2,3,5-triiodothiophene (I), from which other iodothiophenes were obtained. I, m. 82-5° (EtOH), was prepared in 77% yield by refluxing for 100 hrs. a mixture of 1.25 moles thiophene, 800 ml. HOAc, 369 ml. H2O,300 ml. CCl4, 21 ml. concentrated H2SO4, 1.5 moles iodine, and 0.77 moles HIO3, adding H2O and CCl4, extracting, washing, drying, and removing CCl4. A solution of 0.1 mole I in 300 ml. anhydrous Et2O was added to 100 ml. 1.03N BuLi at -70° to give a 63% yield of 2,4-diiodothiophene (II), b10 142-4.5°, which, when added then to an equivalent amount of BuLi at -70° and the resulting solution poured onto CO2 and hydrolyzed, gave 53% 4-iodo-2-thiophene-carboxylic acid (III), m. 115-17°; Me ester m. 41.5-3°. The reaction of 2 moles BuLi with 1 mole II gave 80% 2,4-thiophenedicarboxylic acid, m. 299-301°. Addition of 0.238 moles I continuously to a boiling mixture of 100 ml. H2O, 70 g. Zn powder, and 40 ml. HOAc with immediate distillation of the product gave 25.5 g. (52%) 3-iodothiophene (IV), b9 66-8°, n20D 1.6584, and 10 g. thiophene. The reaction of IV with iodine-HIO3 gave 73% 2,3-diiodothiophene (V), b10 133-5°, and 0.5% II, whereas the reaction of IV in C6H6 with HgO and iodine gave a mixture b14 14650°, which was shown by infrared analysis to contain 93% V and 7% II. Iodination of Me 2-thiophenecarboxylate with iodine and HIO3 gave 45% Me 5-iodo-2-thiophenecarboxylate (VI), m. 88-9° (ligroine), containing 3% Me 4-iodo-2-thiophenecarboxylate. Refluxing VI 10 hrs. with methanolic KOH gave 80% 5-iodo-2-thiophenecarboxylic acid, m. 132-4° (EtOH). To 33 g. 5,5′-dicarboxy-2,2′-bithienyl, prepared by refluxing BuLi and 2,2′-bithienyl and pouring the mixture onto CO2, was added dropwise 60 g. SOCl2, the mixture refluxed 60 hrs., excess SOCl2 removed, 150 ml. anhydrous MeOH added dropwise, and the mixture refluxed 21 hrs. to give 31 g. (85%) 5,5′-dicarbomethoxy-2,2′-bi-thienyl (VII), m. 208-10°. Addition of 26 g. iodine to a mixture of 28 g. VII and 32 g. Hg(OAc)2 in HOAc at 95° followed by stirring at 100° for 72 hrs. and continuously extracting with Et2O for 72 hrs. gave 26.6 g. (65%) 3-iodo-5,5′-dicarbomethoxy-2,2′-bithienyl, m. 127.5-9° (ligroine). To BuLi at -70° was added 2,3-di-iodothiophene in Et2O, then CuCl2, and the mixture worked up to give 25% 3,3′-diiodo-2,2′-bithienyl (VIII), m. 149.5-51° (ligroine). Prepared similarly from I was 3,3′,5,5′-tetraiodo-2,2′-bi-thienyl, m. 190.5-2° (ligroine).

Arkiv foer Kemi published new progress about IR spectra. 88105-22-0 belongs to class iodides-buliding-blocks, and the molecular formula is C6H5IO2S, Product Details of C6H5IO2S.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

D’Auria, Maurizio; Mauriello, Giacomo published the artcile< Reevaluation of benzyltrimethylammonium dichloroiodide, previously reported to be a selective iodinating agent>, Name: Methyl 5-iodothiophene-2-carboxylate, the main research area is benzyltrimethylammonium dichloroiodate chlorination agent; thiophenecarboxylate chloro.

Benzyltrimethylammonium dichloroiodate [N,N,N-trimethylbenzenemethanaminium dichloroiodate(1-)], previously reported as an iodinating agent of thiophenes, appears to be a selective chlorinating agent of both thienyl and furyl derivatives containing a carbonyl group. Treatment of Me 2-thiophenecarboxylate with benzyltrimethylammonium dichloroiodate/ZnCl2/AcOH gave Me 5-iodo-2-thiophenecarboxylate, Me 4,5-diiodo-2-thiophenecarboxylate, and Me 5-chloro-2-thiophenecarboxylate.

Synthesis published new progress about Chlorination. 88105-22-0 belongs to class iodides-buliding-blocks, and the molecular formula is C6H5IO2S, Name: Methyl 5-iodothiophene-2-carboxylate.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Yang, Tao; Chen, Xianxiao; Rao, Weidong; Koh, Ming Joo published the artcile< Broadly Applicable Directed Catalytic Reductive Difunctionalization of Alkenyl Carbonyl Compounds>, Computed Properties of 167479-01-8, the main research area is alkenyl carbonyl reductive difunctionalization nickel catalyst.

Catalytic alkene difuntionalization is a convenient platform for introducing complexity in mols. and has wide applications in organic synthesis. Yet a compelling challenge that remains to be solved is the regioselective insertion of two highly functionalized carbon-based moieties, derived from stable and readily available organohalide electrophiles without the need for pre-synthesized organometallic reagents, across C=C bonds in unactivated alkyl-substituted alkenes. That catalytic amounts of an inexpensive Ni-based catalyst, in combination with a readily recyclable 8-aminoquinoline directing group, promotes efficient and site-selective addition of two different organohalides (iodides and bromides) across aliphatic alkenes under mild reductive conditions. Compared to previous studies, this protocol exhibits broad and complementary functional group tolerance that extends to aryl-alkylation, alkenyl-alkylation, and dialkylation transformations. The utility of the strategy is demonstrated through concise synthesis of biol. active mols. Kinetic studies and other control experiments shed further light on the mechanistic underpinnings of the multicomponent reaction.

Chem published new progress about Alkenylation. 167479-01-8 belongs to class iodides-buliding-blocks, and the molecular formula is C8H16INO2, Computed Properties of 167479-01-8.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Namkung, Moses J.; Fletcher, T. Lloyd published the artcile< Derivatives of fluorene. XXV. Fluorofluorenes. 6>, Application In Synthesis of 2265-92-1, the main research area is FLUORINATION FLUORENES; FLUORENES FLUORO.

The synthesis of 5,6,7,8-tetrafluoro-2-acetamidofluorene, 1,4,7-trifluoro-2-acetamidofluorene (I), and 5,8-difluoro-2-acetamidofluorene, of a 1,2,3,4,7-penta-, a 1,2,3,4-tetra-, a 1,2,4,7-tetra-, a 1,4,7-tri-, and a 1,4-difluorofluorenone, and of related derivatives is reported together with their ir absorption data. Nitration of polyfluorofluorenones which have an unsubstituted 2 (or 7) position occurs at that position. An unexpected directive effect was observed in the nitration of 4,7-difluoro-2-acetamidofluorene.

Canadian Journal of Chemistry published new progress about 2265-92-1. 2265-92-1 belongs to class iodides-buliding-blocks, and the molecular formula is C6H3F2I, Application In Synthesis of 2265-92-1.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Satonaka, Hajime; Abe, Kazuhisa; Hirota, Minoru published the artcile< Carbon-13 NMR spectra of substituted 2-thiophenecarboxylic acid methyl esters and MNDO calculations>, Electric Literature of 88105-22-0, the main research area is NMR methyl thiophenecarboxylate; MNDO methyl thiophenecarboxylate; conformation methyl thiophenecarboxylate.

The 13C NMR spectra have been reported on substituted 2-thiophenecarboxylic acid Me esters. The chem. shift of ring carbons in Me 4- and 5-substituted 2-thiophenecarboxylates was correlated linearly with that of the corresponding carbons in substituted thiophenes. Plots of the 13C-H coupling constants also showed a good linear relation. The 13C NMR data were interpreted by the stable conformation and percent s character of C-H bonds obtained by MNDO calculation

Bulletin of the Chemical Society of Japan published new progress about Electron configuration. 88105-22-0 belongs to class iodides-buliding-blocks, and the molecular formula is C6H5IO2S, Electric Literature of 88105-22-0.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Lakshmi, Balagopal; Kung, Mei-Ping; Lieberman, Brian; Zhao, Jun; Waterhouse, Rikki; Kung, Hank F. published the artcile< (R)-N-Methyl-3-(3-125I-pyridin-2-yloxy)-3-phenylpropan-1-amine: a novel probe for norepinephrine transporters>, Application In Synthesis of 188057-20-7, the main research area is radioiodinated iodonisoxetine derivative preparation biodistribution norepinephrine transporter PET imaging.

Alterations in serotonin and norepinephrine neuronal functions have been observed in patients with major depression. Several antidepressants bind to both serotonin transporters and norepinephrine transporters (NET). The ability to image NET in the human brain would be a useful step toward understanding how alterations in NET relate to disease. In this study, we report the synthesis and characterization of a new series of derivatives of iodonisoxetine, a known radioiodinated probe. The most promising, (R)-N-methyl-3-(3-iodopyridin-2-yloxy)-3-phenylpropylamine (PYINXT), displayed a high and saturable binding to NET, with a Kd value of 0.53 ± 0.03 nM. Biodistribution studies of (R)-N-methyl-3-(3-125I-pyridin-2-yloxy)-3-phenylpropan-1-amine in rats showed moderate initial brain uptake (0.54% dose/organ at 2 min) with a relatively fast washout from the brain (0.16% dose/organ at 2 h) as compared to [125I]INXT. The hypothalamus (a NET-rich region)-to-striatum (a region devoid of NET) ratio was found to be 2.14 at 4 h after i.v. injection. Preliminary results suggest that this improved iodinated ligand, when labeled with 123I, may be useful for mapping NET-binding sites with single photon emission computed tomog. in the living human brain.

Nuclear Medicine and Biology published new progress about Brain (uptake). 188057-20-7 belongs to class iodides-buliding-blocks, and the molecular formula is C5H4INO, Application In Synthesis of 188057-20-7.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Li, Bing; Yang, Zhan; Gong, Wenqi; Chen, Xinhui; Bruce, Duncan W.; Wang, Shengyue; Ma, Huili; Liu, Yu; Zhu, Weiguo; Chi, Zhenguo; Wang, Yafei published the artcile< Intramolecular Through-Space Charge Transfer Based TADF-Active Multifunctional Emitters for High Efficiency Solution-Processed OLED>, Application In Synthesis of 2265-92-1, the main research area is thermally activated delayed fluorescence emitter organic light emitting diode.

Thermally activated delayed fluorescence (TADF) has been explored actively in luminescent organic materials. Yet, realizing such TADF-active, multifunctional emitters with high emission efficiency still remains hugely challenging. In this context, a series of twist-conjugated organic mols. bearing diphenylsulfone and 9,9-dimethylacridine moieties are designed and prepared, and are found to show, in one mol., TADF, room-temperature phosphorescence, triboluminescence, and aggregation-induced emission enhancement. In addition, remarkably high photoluminescence quantum efficiency, up to ≈100%, is achieved for these novel mols. Single-crystal anal. and theor. calculations reveal that the through-space charge transfer (TSCT) effect in these mols. is responsible for both the multifunctional emission and high emission efficiency. A maximum external quantum efficiency of 20.1% is achieved, which is among the highest recorded in a solution-processable device containing TSCT-based TADF materials. These results illustrate a new approach to achieving highly efficient TADF-active, multifunctional emitters.

Advanced Optical Materials published new progress about Absorption spectroscopy. 2265-92-1 belongs to class iodides-buliding-blocks, and the molecular formula is C6H3F2I, Application In Synthesis of 2265-92-1.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Gruber, Stefan; Waser, Valerie; Thiel, Zacharias; Ametamey, Simon M. published the artcile< Prodrug Approach toward the Development of a PET Radioligand for Imaging the GluN2A Subunits of the NMDA Receptor>, Application In Synthesis of 1391728-13-4, the main research area is fluorine 18 labeled prodrug AFA233 phosphate ester preparation.

A straightforward synthesis of a F-18-labeled prodrug of AFA233 is reported. The key step in the preparation of [18F]AFA233-prodrug is the selective deprotection of the tert-Bu protection groups of the quinoxalinedione moiety without cleavage of the tert-butyl-S-acyl-2-thioethyl protection groups on the phosphate esters. The preparation of the nonradioactive prodrug reference compound of AFA233 is reported.

Organic Letters published new progress about Imaging (F-18-labeled prodrug AFA233). 1391728-13-4 belongs to class iodides-buliding-blocks, and the molecular formula is C9H10FIO, Application In Synthesis of 1391728-13-4.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Koo, Seung Moh; Vendola, Alex J.; Momm, Sarah Noemi; Morken, James P. published the artcile< Alkyl Group Migration in Ni-Catalyzed Conjunctive Coupling with C(sp3) Electrophiles: Reaction Development and Application to Targets of Interest>, Recommanded Product: tert-Butyl (3-iodopropyl)carbamate, the main research area is alkyl migration cross coupling nickel catalyst; organoboronic ester preparation cross coupling nickel catalyst; coniine indolizidine 209D preparation cross coupling nickel catalyst.

A catalytic conjunctive cross-coupling reaction was developed that allows the construction of chiral organoboronic esters from alkylboron ate complexes and alkyl iodide electrophiles. The process occurs most efficiently with a Ni/Pybox-comprised catalyst and with an acenaphthoquinone-derived boron ligand. Because of the broad functional group tolerance of this reaction, it can be a versatile tool for organic synthesis. Applications to the construction of (R)-coniine and (-)-indolizidine 209D are described.

Organic Letters published new progress about Boronic acids, esters Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 167479-01-8 belongs to class iodides-buliding-blocks, and the molecular formula is C8H16INO2, Recommanded Product: tert-Butyl (3-iodopropyl)carbamate.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com