Month: April 2022

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 2-Bromo-6-(bromomethyl)naphthalene(SMILESS: BrCC1=CC2=CC=C(Br)C=C2C=C1,cas:305798-02-1) is researched.Related Products of 707-61-9. The article 《Utilization of Donor-Acceptor Interactions for the Catalytic Acceleration of Nucleophilic Additions to Aromatic Carbonyl Compounds》 in relation to this compound, is published in Angewandte Chemie, International Edition. Let’s take a look at the latest research on this compound (cas:305798-02-1).

A conceptually new method for the catalytic electrophilic activation of aromatic carbonyl substrates, by utilizing donor-acceptor interactions between an electron-deficient macrocyclic boronic ester host ([2+2]BTH-F) and an aromatic carbonyl guest substrate, was realized. In the presence of a catalytic amount of [2+2]BTH-F, dramatic acceleration of the nucleophilic addition of a ketene silyl acetal towards either electron-rich aromatic aldehydes or ketones was achieved. Several control experiments confirmed that inclusion of the aromatic substrates within [2+2]BTH-F, through efficient donor-acceptor interactions, is essential for the acceleration of the reaction.

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

Related Products of 707-61-9. 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: 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide, is researched, Molecular C11H13OP, CAS is 707-61-9, about Biphilic Organophosphorus-Catalyzed Intramolecular Csp2-H Amination: Evidence for a Nitrenoid in Catalytic Cadogan Cyclizations. Author is Nykaza, Trevor V.; Ramirez, Antonio; Harrison, Tyler S.; Luzung, Michael R.; Radosevich, Alexander T..

A small-ring phosphacycloalkane (1,2,2,3,4,4-hexamethylphosphetane) (I) catalyzes intramol. C-N bond forming heterocyclization of o-nitrobiaryls and o-nitrostyrenes in the presence of a hydrosilane terminal reductant. The method provides scalable access to diverse carbazole and indole compounds under operationally trivial homogeneous organocatalytic conditions, as demonstrated by 17 examples conducted on 1 g scale. In situ NMR reaction monitoring studies support a mechanism involving catalytic PIII/PV=O cycling, where tricoordinate phosphorus compound I represents the catalytic resting state. For the catalytic conversion of o-nitrobiphenyl to carbazole, the kinetic reaction order was determined for phosphetane catalyst I (first order), substrate (first order), and phenylsilane (zeroth order). For differentially 5-substituted 2-nitrobiphenyls, the transformation is accelerated by electron-withdrawing substituents (Hammett factor ρ = +1.5), consistent with the accrual of neg. charge on the nitro substrate in the rate-determining step. DFT modeling of the turnover-limiting deoxygenation event implicates a rate-determining (3 + 1) cheletropic addition between the phosphetane catalyst and 2-nitrobiphenyl substrate to form an unobserved pentacoordinate spiro-bicyclic dioxazaphosphetane, which decomposes via (2 + 2) cycloreversion giving 1 equiv of phosphetane P-oxide and 2-nitrosobiphenyl. Exptl. and computational investigations into the C-N bond forming event suggest the involvement of an oxazaphosphirane (2 + 1) adduct between I and 2-nitrosobiphenyl, which evolves through loss of phosphetane P-oxide to give the observed carbazole product via C-H insertion in a nitrene-like fashion.

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

Application In Synthesis of H-Trp-OMe.HCl. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: H-Trp-OMe.HCl, is researched, Molecular C12H15ClN2O2, CAS is 7524-52-9, about Access to Benzazepinones by Pd-Catalyzed Remote C-H Carbonylation of γ-Arylpropylamine Derivatives. Author is Martinez-Mingo, Mario; Rodriguez, Nuria; Gomez Arrayas, Ramon; Carretero, Juan C..

A general method for the construction of seven-membered rings through Pd-catalyzed C(sp2)-H carbonylation at the remote ε-position of γ-arylpropylamine derivatives, including chiral α-amino acids, was developed using Mo(CO)6 as the CO source, furnishing richly functionalized benzo[c]azepin-1-one derivatives The readily removable N-SO2Py protecting/directing group provides high levels of chemo-, regio- and diastereoselectivity. Furthermore, this method is amenable to the postsynthetic modification of complex mols. such as small peptides.

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

Category: dioxole. 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. 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 Coordination-Induced Stereocontrol over Carbocations: Asymmetric Reductive Deoxygenation of Racemic Tertiary Alcohols.

The inherent difficulty in eliciting facial control over carbocations has limited their utility as intermediates in asym. catalysis. We have now shown that a docking strategy involving the reversible coordination of a substrate to a chiral transition-metal catalyst can be used to enable highly stereoselective nucleophilic attack on intermediate tertiary carbocations. This approach has been implemented to achieve the first example of enantioselective reductive deoxygenation of tertiary alcs. This reduction occurs with high enantio- (up to 96% ee) and regioselectivity (up to >50:1 rr) by applying a novel Hantzsch ester analog as a convenient hydride source. In-depth mechanistic studies support the involvement of a tertiary carbocation that is coordinated to the iridium metal center via the key allene moiety.

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

Safety of 2-Bromomethyl-1,3-dioxolane. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 2-Bromomethyl-1,3-dioxolane, is researched, Molecular C4H7BrO2, CAS is 4360-63-8, about Mass Spectra of New Heterocycles: XXIII. Electron Impact and Chemical Ionization Study of 5-[(Cyanomethyl)sulfanyl]- and 5-[(1,3-Dioxolan-2-ylmethyl)sulfanyl]-1H-pyrrol-2-amines. Author is Klyba, L. V.; Nedolya, N. A.; Sanzheeva, E. R.; Tarasova, O. A..

The fragmentation of pyrroles I [R1 = R2 = Me, Et, n-Pr; R3 = Me, s-Bu, c-hexyl, etc.; -R1R2- = -(CH2)4-, -(CH2)5-, -(CH2)2O(CH2)2; R4 = CN, 1,3-dioxolan-2-yl] under electron impact (70 eV) and chem. ionization with methane as reactant gas has been studied for the first time. Electron impact ionization of 5-[(cyanomethyl)sulfanyl]-substituted pyrroles generates low-stability mol. ions {M+., Irel 4-22%; compared to Irel 16-69% for 5-[(1,3-dioxolan-2-ylmethyl)sulfanyl] analogs} whose primary fragmentation involves cleavage of the C-S bond with expulsion of NCCH2 radical. Other fragmentation pathways of the mol. ions include formation of [M – CHR4]+. ions (R4 = CN) and substituent decomposition products. The mass spectra of 5-[(1,3-dioxolan-2-ylmethyl)sulfanyl]pyrroles characteristically show [M – SCH2R4]+ ion peak. The most intense ion peaks in the chem. ionization mass spectra of 5-[(cyanomethyl)sulfanyl] derivatives are those of M+. (Irel 18-69%) and [M + H]+ (Irel 34-100%). Both 5-[(cyanomethyl)sulfanyl]- and 5-[(1,3-dioxolan-2-ylmethyl)sulfanyl]pyrroles decompose mainly through cleavage of the CH2-S and C5-S bonds with the formation of stable [M – CH2R4]+ (Irel 92-100%), [M + H – CH2R4]+. (Irel 22-75%), and [M + H – SCH2R4]+. ions (Irel 6-25%).

Although many compounds look similar to this compound(4360-63-8)Safety of 2-Bromomethyl-1,3-dioxolane, numerous studies have shown that this compound(SMILES:BrCC1OCCO1), has unique advantages. If you want to know more about similar compounds, you can read my other articles.

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

Name: 5-(11bR)-Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-yl-5H-dibenz[b,f]azepine. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. 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 Synthesis of C5-Allylindoles through an Iridium-Catalyzed Asymmetric Allylic Substitution/Oxidation Reaction Sequence of N-Alkyl Indolines. Author is Lu, Jiamin; Xu, Ruigang; Zeng, Haixia; Zhong, Guofu; Wang, Meifang; Ni, Zhigang; Zeng, Xiaofei.

Iridium/Bronsted acid cooperative catalyzed asym. allylic substitution reactions at the C5 position of indolines I (R = Bn, PMB; R1 = 2-Me, 2-Ph, 2,3-(Me)2, etc.) have been reported for the first time. The highly efficient protocol allows rapid access to various C5-allylated products (R/S)-II (Ar = C6H5, 2-BrC6H4, 2-naphthyl, etc.) and III in good to high yields (48-97%) and enantioselectivities (82% to >99% ee) with wide functional group tolerance. The transformations allow not only the formation of C5-allylindoline derivatives II but also the synthesis of C5-allylindoles III in good yields and excellent stereoselectivities via an allylation/oxidation reaction sequence.

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

Lu, Meng-Chen; Zhang, Xian; Wu, Feng; Tan, Shi-Jie; Zhao, Jing; You, Qi-Dong; Jiang, Zheng-Yu published an article about the compound: H-Trp-OMe.HCl( cas:7524-52-9,SMILESS:N[C@@H](CC1=CNC2=CC=CC=C12)C(OC)=O.[H]Cl ).Safety of H-Trp-OMe.HCl. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:7524-52-9) through the article.

The transcription factor Nrf2 is a key regulator of cytoprotective system, and enhancing Nrf2 activity can protect cells from various insults and threats. Directly disrupting Keap1-Nrf2 protein-protein interactions has been regarded as a promising way to activate Nrf2. We reported here the first identification of amino acids as preferred substituents to design potent Keap1-Nrf2 inhibitors. Comprehensive structure-activity anal. identified Pro as a preferred substituent, obtaining a potent inhibitor 35 with an IC50 of 43 nM in the competitive fluoresce polarization (FP) assay and a Kd value of 53.7 nM for Keap1 protein in the isothermal titration calorimetry (ITC) assay. The Pro analog 35 exhibited tight and prolonged Keap1 binding in vitro and in cells, and treatment with 35 activated Nrf2-regulated cytoprotective response and antagonized acetaminophen-induced liver injury both in cellular and in vivo models. This work not only provides a useful tool to further explore the therapeutic potential of Keap1-Nrf2 inhibition but also enriches the diversity of chem. structures suitable for the Keap1-Nrf2 interface.

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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.Tong, Rong; Pang, Xiaoyan; Sun, Jing; Ding, Zhiwen; Jia, Jizhang researched the compound: 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide( cas:707-61-9 ).SDS of cas: 707-61-9.They published the article 《Synthesis and application of aqueous polycarbodiimide crosslinking agent(I): aqueous cationic polycarbodiimide crosslinking agent》 about this compound( cas:707-61-9 ) in Zhongguo Pige. Keywords: aqueous cationic polycarbodiimide crosslinking agent synthesis. We’ll tell you more about this compound (cas:707-61-9).

Aqueous cationic polycarbodiimide crosslinking agent was synthesized with isophorone diisocyanate (IPDI), polypropylene glycol (PPG400), N,N-dimethylethanolamine (DMEA) and 3-methyl-1-phenyl-2-phosopholene-1-oxide (MPPO) as raw materials. The influences of synthesis conditions such as the dosage of catalyst, reaction time, reaction temperature, nitrogen jet velocity, hydrophilic end-blocking agent, end-blocking temperature and the dosage of end-blocking agent on the blocking reaction were investigated. The developed crosslinking agents were applied to protein finishing agent. And it is found that the properties of obtained finishing film agent are better in the water resistance, alkali resistance, solvent resistance and flexibility. Also, the tensile strength of film increases with a little decrease in brightness and transparency.

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

Category: dioxole. 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: 2-Bromomethyl-1,3-dioxolane, is researched, Molecular C4H7BrO2, CAS is 4360-63-8, about Transition-Metal-Free Deconstructive Lactamization of Piperidines. Author is Romero-Ibanez, Julio; Cruz-Gregorio, Silvano; Sandoval-Lira, Jacinto; Hernandez-Perez, Julio M.; Quintero, Leticia; Sartillo-Piscil, Fernando.

One of the major challenges in organic synthesis is the activation or deconstructive functionalization of unreactive C(sp3)-C(sp3) bonds, which requires using transition or precious metal catalysts. We present here an alternative: the deconstructive lactamization of piperidines without using transition metal catalysts. To this end, we use 3-alkoxyamino-2-piperidones, which were prepared from piperidines through a dual C(sp3)-H oxidation, as transitory intermediates. Exptl. and theor. studies confirm that this unprecedented lactamization occurs in a tandem manner involving an oxidative deamination of 3-alkoxyamino-2-piperidones to 3-keto-2-piperidones, followed by a regioselective Baeyer-Villiger oxidation to give N-carboxyanhydride intermediates, which finally undergo a spontaneous and concerted decarboxylative intramol. translactamization.

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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.Mas-Rosello, Josep; Smejkal, Tomas; Cramer, Nicolai researched the compound: 2-Bromomethyl-1,3-dioxolane( cas:4360-63-8 ).HPLC of Formula: 4360-63-8.They published the article 《Iridium-catalyzed acid-assisted asymmetric hydrogenation of oximes to hydroxylamines》 about this compound( cas:4360-63-8 ) in Science (Washington, DC, United States). Keywords: iridium catalyzed acid assisted asym hydrogenation oxime hydroxylamine. We’ll tell you more about this compound (cas:4360-63-8).

Asym. hydrogenations are among the most practical methods for the synthesis of chiral building blocks at industrial scale. The selective reduction of an oxime to the corresponding chiral hydroxylamine derivative remains a challenging variant because of undesired cleavage of the weak nitrogen-oxygen bond. We report a robust cyclometalated iridium(III) complex bearing a chiral cyclopentadienyl ligand as an efficient catalyst for this reaction operating under highly acidic conditions. Valuable N-alkoxy amines can be accessed at room temperature with nondetected overredn. of the N-O bond [e.g., (E)-I → (S)-II (97%, 97.5:2.5 er)]. Catalyst turnover numbers up to 4000 and enantiomeric ratios up to 98:2 are observed The findings serve as a blueprint for the development of metal-catalyzed enantioselective hydrogenations of challenging substrates.

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