Category: 21286-54-4

Rojas Cabrera, Haydee published the artcileHomochiral L-prolinamido-sulfonamides and their use as organocatalysts in aldol reactions, Computed Properties of 21286-54-4, the publication is Tetrahedron: Asymmetry (2015), 26(4), 163-172, database is CAplus.

The synthesis of new homochiral L-prolinamido-sulfonamides 1-7 from enantiomerically pure (R,R)-11,12-diamino-9,10-dihydro-9,10-ethanoanthracene (R,R)-8 is reported. The L-prolinamido-sulfonamides 1-7 were tested as organocatalysts (10 mol %) in the aldol reaction of p-nitrobenzaldehyde and acetone in dichloromethane at room temperature in the presence of water (1 equiv) and acetic acid (20 mol %) giving good to high yields and enantioselectivities. Catalyst I (10 mol %) afforded the best results in the aldol reaction of acetone with p-substituted-benzaldehydes with electron withdrawing groups (i.e., nitro, cyano, bromo and chloro, up to 97% yield and 90% ee). The origin of the enantioselective induction was modeled using DFT methods. The estimated enantioselectivity for the model system is consistent with the exptl. data.

Tetrahedron: Asymmetry published new progress about 21286-54-4. 21286-54-4 belongs to chlorides-buliding-blocks, auxiliary class Chiral,Chloride,Sulfonyl chlorides,Aliphatic cyclic hydrocarbon,Ketone, name is ((1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride, and the molecular formula is C10H15ClO3S, Computed Properties of 21286-54-4.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Liu, Gang published the artcileDiscovery of Novel Macrocyclic Hedgehog Pathway Inhibitors Acting by Suppressing the Gli-Mediated Transcription, Computed Properties of 21286-54-4, the publication is Journal of Medicinal Chemistry (2017), 60(19), 8218-8245, database is CAplus and MEDLINE.

A systemic medicinal chem. campaign was conducted based on a literature hit compound I bearing the 4,5-dihydro-2H-benzo[b][1,5]oxazocin-6(3H)-one core through cyclization of two side substituents of the bicyclic skeleton combined with N-atom walking or ring walking and the central ring expansion or extraction approaches, leading to several series of structurally unique tricyclic compounds Among these, compound II was identified as the most potent against the Hedgehog (Hh) signaling pathway showing an IC₅₀ value of 23 nM. Mechanism studies indicated that compound II inhibited the Hh signaling pathway by suppressing the expression of the transcriptional factors Gli rather than by interrupting the binding of Gli with DNA. We further observed that II was equally potent against both Smo wild type and the two major resistant mutants (Smo D473H and Smo W535L). It potently inhibited the proliferation of medulloblastoma cells and showed significant tumor growth inhibition in the ptch± ;p53-/- medulloblastoma allograft mice model. Though more studies are needed to clarify the precise interaction pattern of II with Gli, its promising in vitro and in vivo properties encourage further profiling as a new-generation Hh signaling inhibitor to treat tumors primarily or secondarily resistant to current Smo inhibitors.

Journal of Medicinal Chemistry published new progress about 21286-54-4. 21286-54-4 belongs to chlorides-buliding-blocks, auxiliary class Chiral,Chloride,Sulfonyl chlorides,Aliphatic cyclic hydrocarbon,Ketone, name is ((1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride, and the molecular formula is C10H15ClO3S, Computed Properties of 21286-54-4.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Axer, Alexander published the artcileHarnessing the Maltodextrin Transport Mechanism for Targeted Bacterial Imaging: Structural Requirements for Improved in vivo Stability in Tracer Design, Application In Synthesis of 21286-54-4, the publication is ChemMedChem (2018), 13(3), 241-250, database is CAplus and MEDLINE.

Diagnosis and localization of bacterial infections remains a significant clin. challenge. Harnessing bacteria-specific metabolic pathways, such as the maltodextrin transport mechanism, may allow specific localization and imaging of small or hidden colonies. This requires that the intrabacterial tracer accumulation provided by the transporter is matched by high serum stability of the tracer mol. Herein, radiolabeled maltodextrins of varying chain lengths and with free nonreducing/reducing ends are reported and their behavior against starch-degrading enzymes in the blood, which compromise their serum stability, is evaluated. Successful single-photon emission computed tomog. (SPECT) imaging is shown in a footpad infection model in vivo by using the newly developed model tracer, [^99mTc]MB1143, and the signal is compared with that of ¹⁸F-fluorodeoxyglucose positron emission tomog. ([¹⁸F]FDG-PET) as a nonbacterial specific marker for inflammation. Although the [^99mTc]MB1143 imaging signal is highly specific, it is low, most probably due to insufficient serum stability of the tracer. A series of stability tests with different ¹⁸F-labeled maltodextrins finally yielded clear structural guidelines regarding substitution patterns and chain lengths of maltodextrin-based tracers for nuclear imaging of bacterial infections.

ChemMedChem published new progress about 21286-54-4. 21286-54-4 belongs to chlorides-buliding-blocks, auxiliary class Chiral,Chloride,Sulfonyl chlorides,Aliphatic cyclic hydrocarbon,Ketone, name is ((1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride, and the molecular formula is C10H15ClO3S, Application In Synthesis of 21286-54-4.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Jain, Nikita published the artcileOxidative Cyclization of Naphtholic Sulfonamides Mediated by a Chiral Hypervalent Iodine Reagent: Asymmetric Synthesis versus Resolution, HPLC of Formula: 21286-54-4, the publication is Synlett (2019), 30(10), 1222-1227, database is CAplus.

A chiral aryl iodide e.g., I promotes the enantioselective oxidative cyclization of 1-naphtholic sulfonamides II (R¹ = H, Cl, Ph, 3,5-di(trifluoromethyl)phenyl, etc.; R² = Me, Bn, 4-methylphenyl, 4-nitrophenyl) and III (R = H, OMe), albeit in moderate ee and low yield. The products (R)/(S)-IV and V tend to crystallize as conglomerates. Recrystallization thus increases their ee to > 99% ee. This highly enantioenriched material provides seed crystals for the resolution of racemate (±)-1′-(methylsulfonyl)-1H-spiro[naphthalene-2,2′-pyrrolidine]-1-one (prepared in high yield by oxidative cyclization with (diacetoxyiodo)benzene in trifluoroacetic acid) by coupled preferential crystallization This enables the production of significant quantities of highly enantioenriched products, despite the low efficiency of the enantioselective reaction.

Synlett published new progress about 21286-54-4. 21286-54-4 belongs to chlorides-buliding-blocks, auxiliary class Chiral,Chloride,Sulfonyl chlorides,Aliphatic cyclic hydrocarbon,Ketone, name is ((1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride, and the molecular formula is C10H15ClO3S, HPLC of Formula: 21286-54-4.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Ma, Hao published the artcileDesign and Synthesis of Bridging Chiral p-t-Butylcalix[4]arene Tetrahydroisoquinolines and Their Application in Henry Reaction as Chiral Organocatalysts, Application In Synthesis of 21286-54-4, the publication is ChemistrySelect (2019), 4(15), 4642-4646, database is CAplus.

A pair of bridging chiral p-t-butylcalix[4]arenes (2a and 2b) (were) synthesized from 1 through homologous anionic ortho-Fries rearrangement, and optically resolved with (1S)-(+)-10-camphorsulfonyl chloride as chiral auxiliary. Bridging chiral p-t-butylcalix[4]arene tetrahydroisoquinolines (9a and 9b) as chiral organocatalysts for Henry reaction were designed and synthesized through the structural modification of 2a and 2b, resp. Compared to the catalytic enantioselectivity of the unmodified tertiary amine (4b: �% ee and 63% yield), those of the tetrahydroisoquinoline derivatives (9b: up to 13.4% ee and 96% yield) were distinctly enhanced. Although the increase magnitude of the catalytic ee is not remarkable, these catalytic results prove that the conformation inversion of calix[4]arene skeleton and the rotational freedom reduction of catalytic amine group indeed bring beneficial effects on the catalytic stereoselectivity.

ChemistrySelect published new progress about 21286-54-4. 21286-54-4 belongs to chlorides-buliding-blocks, auxiliary class Chiral,Chloride,Sulfonyl chlorides,Aliphatic cyclic hydrocarbon,Ketone, name is ((1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride, and the molecular formula is C10H15ClO3S, Application In Synthesis of 21286-54-4.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Liu, Wen-Shan published the artcileBridging Chiral de-tert-Butylcalix[4]arenes: Diastereomeric Crystallization-Based Optical Resolution and Determination of Absolute Configuration, Formula: C10H15ClO3S, the publication is ChemistrySelect (2018), 3(36), 10153-10156, database is CAplus.

A pair of diastereomers were synthesized from the conjugation of bridging chiral de-tert-butylcalix[4]arene racemate and (1S)-(+)-10-camphorsulfonyl chloride. The diastereomeric separation by crystallization was explored in different solvents, temperature and time. The optimal crystallization procedures afforded them in a desirable yield, de and purity. A pair of enantiomers of tert-butylcalix[4]arene were subsequently obtained after their hydrolysis. Moreover, their absolute configurations were determined by X-ray crystallog. anal. The crystallization results can match the large-scale preparation of optically pure de-tert-butylcalix[4]arene in laboratory and industry.

ChemistrySelect published new progress about 21286-54-4. 21286-54-4 belongs to chlorides-buliding-blocks, auxiliary class Chiral,Chloride,Sulfonyl chlorides,Aliphatic cyclic hydrocarbon,Ketone, name is ((1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride, and the molecular formula is C10H15ClO3S, Formula: C10H15ClO3S.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Chai, Guo-Li published the artcileHydroxytetraphenylenes as Chiral Ligands: Application to Asymmetric Darzens Reaction of Diazoacetamide with Aldehydes, Name: ((1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride, the publication is Synthesis (2017), 49(1), 181-187, database is CAplus.

Hydroxytetraphenylenes with rigid conformations are potential candidates for employment as chiral ligands in asym. synthesis. Highly diastereo- and enantioselective Darzens reactions between aldehydes and diazo-N,N-dimethylacetamide are catalyzed by a chiral titanium complex formed in situ from Ti(OⁱPr)₄ and chiral 1,16-dihydroxytetraphenylene, giving cis-glycidic amides in moderate to high yields with excellent enantiomeric purities (40-99% yield, up to 99% ee).

Synthesis published new progress about 21286-54-4. 21286-54-4 belongs to chlorides-buliding-blocks, auxiliary class Chiral,Chloride,Sulfonyl chlorides,Aliphatic cyclic hydrocarbon,Ketone, name is ((1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride, and the molecular formula is C10H15ClO3S, Name: ((1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Chen, Jing-Xing published the artcileSynthesis and Chiroptical Properties of Double-Helical (M)- and (P)-o-Oligophenylenes, Safety of ((1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride, the publication is Organic Letters (2015), 17(17), 4296-4299, database is CAplus and MEDLINE.

All of the M and P isomers of optically pure oligophenylenes with 6, 8, 10, and 12 Ph rings were synthesized and fully characterized. The Suzuki cross-coupling reaction has been revealed to be a viable strategy in the syntheses of tetraphenylene derivatives, which, together with the copper-mediated oxidative cross-coupling reaction, were employed in the quest for the oligophenylenes [e.g., (S,S)-I + (M)-II â†?(M)-III (5%) + (M)-IV (6%) + (M)-V (9%) using t-BuLi/CuCl₂]. X-ray diffraction anal. in combination with sp. rotation and CD spectroscopy unambiguously identified the unique covalent double-helical frameworks of these oligophenylene mols.

Organic Letters published new progress about 21286-54-4. 21286-54-4 belongs to chlorides-buliding-blocks, auxiliary class Chiral,Chloride,Sulfonyl chlorides,Aliphatic cyclic hydrocarbon,Ketone, name is ((1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride, and the molecular formula is C10H15ClO3S, Safety of ((1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Mekala, Shekar published the artcileA Scalable, Nonenzymatic Synthesis of Highly Stereopure Difunctional C₄ Secondary Methyl Linchpin Synthons, Synthetic Route of 21286-54-4, the publication is Journal of Organic Chemistry (2015), 80(3), 1610-1617, database is CAplus and MEDLINE.

In response to the continuing widespread use of heterodifunctional C₄ secondary Me building blocks in asym. synthesis, we have developed a mole-scale, two-step synthesis of a 1:1 mixture of the diastereomers of 3-bromo-2-methyl-1-Pr camphorsulfonate (casylate). One isomer I has been crystallized to >99:1 dr in âˆ?5% yield. Equilibration of the mother liquor (enriched in the other isomer) to a 1:1 mixture and recrystallization significantly raises the overall yield of I. Applications of I include chemoselective Grignard coupling, enabling the very short synthesis of highly stereopure long-chain natural products containing remote, methyl-bearing stereogenic centers [e.g., (R)-tuberculostearic acid (II)], with complete control of configuration. Also, Ag-mediated, completely chemoselective Br displacement from I leads to a range of >99:1 er difunctional synthons. Both applications incorporate concurrent recovery of CasO. The enantiomer of I can be made from com. (1R)-10-CasOH.

Journal of Organic Chemistry published new progress about 21286-54-4. 21286-54-4 belongs to chlorides-buliding-blocks, auxiliary class Chiral,Chloride,Sulfonyl chlorides,Aliphatic cyclic hydrocarbon,Ketone, name is ((1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride, and the molecular formula is C10H15ClO3S, Synthetic Route of 21286-54-4.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Sweetman, Brian A. published the artcileAxially chiral tridentate isoquinoline derived ligands for diethylzinc addition to aldehydes, HPLC of Formula: 21286-54-4, the publication is Tetrahedron (2018), 74(38), 5567-5581, database is CAplus.

The synthesis and resolution of new tridentate isoquinoline-derived ligands was developed. The key steps in the synthetic sequence included successive, chemo-selective Suzuki-Miyaura cross-couplings of 1,3-dichloroisoquinoline with suitable arylboronic acids. The new ligands prepared in this manner were resolved either via mol. complexation with N-benzylcinchonidinium chloride as with 1-[3-(2-hydroxyphenyl)isoquinolin-1-yl]naphthalen-2-ol or via chromatog. separation of its epimeric camphorsulfonates as for 1,3-bis-(2-hydroxynaphthalen-1-yl)isoquinoline. 4-tert-Butyl-2-chloro-6-[1-(2-hydroxymethylnaphthalen-1-yl)isoquinolin-3-yl]phenol was resolved by chiral semi-preparative HPLC. The application of these ligands in the diethylzinc addition to aldehydes was investigated. In certain cases, the desired secondary alcs. were obtained in high yield with excellent enantiomeric excess (ee > 99%) at low catalyst loading (1 mol%).

Tetrahedron published new progress about 21286-54-4. 21286-54-4 belongs to chlorides-buliding-blocks, auxiliary class Chiral,Chloride,Sulfonyl chlorides,Aliphatic cyclic hydrocarbon,Ketone, name is ((1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride, and the molecular formula is C20H21ClN4O4, HPLC of Formula: 21286-54-4.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics