Month: April 2022

SDS of cas: 1265884-98-7. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 5-(11bR)-Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yl-5H-dibenz[b,f]azepine, is researched, Molecular C34H22NO2P, CAS is 1265884-98-7, about Iridium-Catalyzed Enantioselective Indole Cyclization: Application to the Total Synthesis and Absolute Stereochemical Assignment of (-)-Aspidophylline A. Author is Jiang, Shi-Zhi; Zeng, Xue-Yi; Liang, Xiao; Lei, Ting; Wei, Kun; Yang, Yu-Rong.

The first enantioselective total synthesis of (-)-aspidophylline A (I), including assignment of its absolute configuration has been accomplished. A key element of the synthesis is a highly enantioselective indole allylic alkylation/iminium cyclization cascade which was developed by employing a combination of Lewis acid activation and an iridium/ligand catalyst. This strategy relies on the direct use of 2,3-disubstituted indoles with secondary allylic alcs. appended at C2 and heteronucleophiles appended at C3, indoles which are easily prepared from simple starting materials under C-H activation conditions.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 1265884-98-7, is researched, SMILESS is N1(P2OC3=CC=C4C=CC=CC4=C3C5=C6C=CC=CC6=CC=C5O2)C7=CC=CC=C7C=CC8=CC=CC=C81, Molecular C34H22NO2PJournal, Asian Journal of Organic Chemistry called Iridium Catalysed Asymmetric Allylic Substitution Reaction of Indolizine Derivatives, Author is Lu, Jiamin; Wang, Meifang; Xu, Ruigang; Sun, Haizhou; Zheng, Xuan; Zhong, Guofu; Zeng, Xiaofei, the main research direction is allyl alc indolizine iridium catalyst allylic substitution reaction; allylindolizine preparation enantioselective regioselective.Formula: C34H22NO2P.

A highly efficient direct asym. allylic substitution (AAS) reaction of indolizine derivatives with allylic alcs. for accessing enantioenriched indolizine derivatives were realized by combining a chiral iridium complex catalyst with Lewis acid under mild reaction conditions, delivered various chiral allylation products in remarkably high yields and excellent enantioselectivities. This protocol distinguishes itself by availability of the starting materials, mild reaction conditions, broad substrate scope, high yields, excellent selectivity and easy scale-up in a stereoselective manner, which provided a highly efficient protocol for chiral indolizines.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Synthesis of 2-D-L-tryptophan by sequential Ir-catalyzed reactions, published in 2019-04-12, which mentions a compound: 7524-52-9, Name is H-Trp-OMe.HCl, Molecular C12H15ClN2O2, Safety of H-Trp-OMe.HCl.

Herein, we report a practical synthesis of 2-D-L-tryptophan via sequential Ir-catalyzed C-H borylation, and Ir-catalyzed C-2-deborylative deuteration steps. In this synthetic sequence, deprotection of the Boc (Boc = tert-butoxycarbonyl) and Me ester groups proved challenging, due to replacement of deuterium with hydrogen. However, mild deprotection conditions were developed to avoid this D/H scrambling. Further, 2-D-L-tryptophan is stable in many buffers used for biol. studies.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Sandmeier, Tobias; Carreira, Erick M. published the article 《Enantioselective synthesis of cyclic nitrones and oxime ethers by chemoselective allylic alkylation of oximes》. Keywords: cyclic nitrone oxime ether chemoselective enantioselective preparation; oxime allylic alc kinetic resolution; iridium catalyst intramol allylation oxime allylic alc; base scandium mediated iridium catalyst chemoselective allylation hydroxyalkenal oxime; tandem intramol allylation dipolar cycloaddition alkenyl oxime allylic alc.They researched the compound: 5-(11bR)-Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yl-5H-dibenz[b,f]azepine( cas:1265884-98-7 ).Electric Literature of C34H22NO2P. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:1265884-98-7) here.

In the presence of [Ir(cod)Cl]2 and a nonracemic dibenzazepanyl binaphthylphosphoramidite. oximes with attached allylic alc. moieties such as I underwent chemoselective and enantioselective intramol. allylation reactions with kinetic resolution mediated by either dichloroacetic acid or (in some cases) by Sc(OTf)3 and Cs2CO3 to give nonracemic hydroxyalkenyl oximes such as II and either cyclic nitrones such as III or cyclic oxime ethers such as IV, resp. Oximes with pendant alkenes (in addition to the allylic alc. moiety) such as H2C:CH(CH2)3C(:NOH)(CH2)3CH(OH)CH:CH2 underwent tandem allylation and diastereoselective 1,3-dipolar cycloaddition reactions to yield tricyclic oxazolidines such as V. Mixtures of oxime diastereomers underwent convergent allylation to single enantiomers of the nitrone and allylic alc. products. Acylhydrazones with allylic alc. moieties underwent enantioselective allylation reactions to yield azomethine imines; if a pendant alkene was present, a tricyclic pyrazolidine was formed by tandem allylation and 1,3-dipolar cycloaddition The method was used for the formal syntheses of the glycoprotein GP IIb-IIIa receptor antagonist (-)-roxifiban and of the alkaloid (+)-halichlorine.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

Quality Control of 6,7-Dichlorobenzo[d]thiazol-2-amine. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 6,7-Dichlorobenzo[d]thiazol-2-amine, is researched, Molecular C7H4Cl2N2S, CAS is 25150-27-0, about Identification of a novel series of tetrahydrodibenzazocines as inhibitors of 17β-hydroxysteroid dehydrogenase type 3. Author is Fink, Brian E.; Gavai, Ashvinikumar V.; Tokarski, John S.; Goyal, Bindu; Misra, Raj; Xiao, Hai-Yun; Kimball, S. David; Han, Wen-Ching; Norris, Derek; Spires, Thomas E.; You, Dan; Gottardis, Marco M.; Lorenzi, Matthew V.; Vite, Gregory D..

A novel series of 17β-hydroxysteroid dehydrogenase type 3 (17β-HSD3) inhibitors has been identified. These inhibitors, based on a dibenzazocine core, exhibited picomolar to low nanomolar inhibition of 17β-HSD3 in cell-free enzymic as well as in cell-based transcriptional reporter assays.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide, is researched, Molecular C11H13OP, CAS is 707-61-9, about Preparation of phospho sugar analogs and their evaluation as novel anticancer agents, the main research direction is phospho sugar analog preparation anticancer leukemia.Related Products of 707-61-9.

Phospho sugars were prepared by a novel synthetic route starting from phosphorus heterocyclic compounds, 2-phospholenes. The anhydro- and deoxy-phospha sugar derivatives have been revealed to have potential anticancer activities against human leukemia K562 and U937 cell lines. In this article, deoxybromophospho sugars with different numbers of bromo substituents were prepared, and their anticancer activities were evaluated by MTT method. The order of the activities depending on the number of bromo substituent was first revealed, and trideoxytribromotetrofuranose type phospho sugar [2,3,4-tribromo-3-methyl-1-phenylphospholane 1-oxide (4: TBMPPAO)] was the most active among these phospha sugars prepared Diastereomers of dideoxydibromotetrofuranose-type phospho sugar [2,3-dibromo-3-methyl-1-phenylphospholane 1-oxide (2: DBMPPAO)] were separated into four components, and the structure as well as the character of each component was assigned by spectral and chromatog. data as well as by MTT method.The deoxybromophospha sugars have higher antileukemia activity than Gleevec against U937 cells.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Synthesis and application of aqueous polycarbodiimide crosslinking agent(II): aqueous anionic polycarbodiimide crosslinking agent, published in 2011-08-03, which mentions a compound: 707-61-9, Name is 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide, Molecular C11H13OP, Recommanded Product: 707-61-9.

Aqueous anionic polycarbodiimide crosslinking agent was synthesized with isophorone diisocyanate(IPDI), sodium hydroxyethyl sulfonate(SHES) and 3-methyl-1-phenyl-2-phospholene-1-oxide(MPPO) as raw material. The influences of different synthesis conditions such as the hydrophilic end-blocking agent and temperature, as well as the dosage of end-blocking on the blocking reaction were investigated and the optimal technol. condition was obtained. The developed crosslinking agents were introduced to acrylic finishing agent. It show that tensile strength of the film increases from 2.813MPa to 6.147MPa; the swelling rate in water, 0.05mol/L NaOH, Bu acetate decreases from 52.3% to 26.4%, 202.4% to 140.4%, 843.2% to 354.8% resp.; and the rub fastness of dry and wet are improved by adding the crosslinking agent to the acrylic finishing agents.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Frydrych, Jan; Slaveetinska, Lenka Postova; Draccinsky, Martin; Janeba, Zlatko researched the compound: 2-Bromomethyl-1,3-dioxolane( cas:4360-63-8 ).Application of 4360-63-8.They published the article 《Efficient synthesis of α-branched purine-based acyclic nucleosides: scopes and limitations of the method》 about this compound( cas:4360-63-8 ) in Molecules. Keywords: acyclonucleoside preparation; nitrogen heterocycle acetal anhydride alkylation; acyclonucleosides; hemiaminal ether; multi-component reaction; purine. We’ll tell you more about this compound (cas:4360-63-8).

An efficient route to acylated acyclic nucleosides containing a branched hemiaminal ether moiety was reported via three-component alkylation of N-heterocycle (purine nucleobase) with acetal (cyclic or acyclic, variously branched) and anhydride (preferentially acetic anhydride). The procedure employed cheap and easily available acetals, acetic anhydride, and trimethylsilyl trifluoromethanesulfonate (TMSOTf). The multi-component reaction was carried out in acetonitrile at room temperature for 15 min and provides moderate to high yields (up to 88%) of diverse acyclonucleosides branched at the aliphatic side chain. The procedure exhibited a broad substrate scope of N-heterocycles and acetals, and, in the case of purine derivatives, also excellent regioselectivity, giving almost exclusively N-9 isomers.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《2- and 5-Fluoronicotinic acids》. Authors are Beaty, R. D.; Musgrave, W. K. R..The article about the compound:Methyl 5-fluoro-3-pyridinecarboxylatecas:455-70-9,SMILESS:COC(=O)C1=CC(F)=CN=C1).Application In Synthesis of Methyl 5-fluoro-3-pyridinecarboxylate. Through the article, more information about this compound (cas:455-70-9) is conveyed.

5-Aminonicotinic acid (I) (3 g.) in 20 cc. 40% HBF4 at -5° treated with 2.5 g. NaNO2, the mixture kept 1 h., heated 30 min. at 50°, neutralized with Na2CO3, and the resulting salt refluxed 2-3 h. with 3% MeOH-H2SO4, gives 0.3 g. Me 5-fluoronicotinate, m. 48°. The 2-isomer of I (2 g.) in 10 cc. 40% HBF4, diazotized with 1 g. NaNO2 in 10 cc. H2O at 0 to -5°, and the solution kept 1 h. at 0°, heated 1 h. at 50-60°, and basified to pH 5 with NaOH, gives 33% 2-fluoronicotinic acid, m. 164-5°; the Me ester m. 74-5° and the amide m. 124°. 3-Fluoropicolinic acid could not be prepared by this method.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: H-Trp-OMe.HCl, is researched, Molecular C12H15ClN2O2, CAS is 7524-52-9, about Synthesis of Four Optical Isomers of Antiviral Agent NK0209 and Determination of Their Configurations and Activities against a Plant Virus, the main research direction is NK0209 isomer preparation antiviral tobacco mosaic virus antiviral; NK0209; antiviral activity; isomers; spatial configuration; synthesis.Related Products of 7524-52-9.

Previously, we reported for the first time that harmala alkaloids harmine and tetrahydroharmine exhibit activity against plant viruses, and we developed an analog, designated NK0209, that efficiently prevents and controls plant virus diseases. Here, to investigate the influence of the spatial configuration of NK0209 on its antiviral activities, we synthesized its four optical isomers, determined their configurations, and evaluated their activities against tobacco mosaic virus. All four isomers were significantly more active than ningnanmycin, which is one of the most successful com. antiviral agents, with in vivo inactivation, cure, and protection rates of 57.3±1.9%, 54.2±3.3%, 55.0±4.1% at 500μg/mL. Furthermore, anal. of structure-activity relationships demonstrated for the first time that the spatial conformation of NK0209 is an important determinant of its antiviral activity, and our results provide information about the possible optimum configuration for interaction of this mol. with its target protein.

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Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem