Category: 1530-33-2

Troeger, Armin; Svensson, Glenn P.; Galbrecht, Hans-Martin; Twele, Robert; Patt, Joseph M.; Bartram, Stefan; Zarbin, Paulo H. G.; Segraves, Kari A.; Althoff, David M.; von Reuss, Stephan; Raguso, Robert A.; Francke, Wittko published the artcile< Tetranorsesquiterpenoids as Attractants of Yucca Moths to Yucca Flowers>, SDS of cas: 1530-33-2, the main research area is Tegeticula Yucca flower tetranorsesquiterpenoids attractants; DMNT-derivatives; Floral scent; Pollinator attraction; Structure elucidation; Tetranorsesquiterpenoids; Total synthesis; Yucca.

The obligate pollination mutualism between Yucca and yucca moths is a classical example of coevolution. Oviposition and active pollination by female yucca moths occur at night when Yucca flowers are open and strongly scented. Thus, floral volatiles have been suggested as key sensory signals attracting yucca moths to their host plants, but no bioactive compounds have yet been identified. In this study, we showed that both sexes of the pollinator moth Tegeticula yuccasella are attracted to the floral scent of the host Yucca filamentosa. Chem. anal. of the floral headspace from six Yucca species in sections Chaenocarpa and Sarcocarpa revealed a set of novel tetranorsesquiterpenoids putatively derived from (E)-4,8-dimethyl-1,3,7-nonatriene. Their structure elucidation was accomplished by NMR anal. of the crude floral scent sample of Yucca treculeana along with GC/MS anal. and confirmed by total synthesis. Since all these volatiles are included in the floral scent of Y. filamentosa, which has been an important model species for understanding the pollination mutualism, we name these compounds filamentolide, filamentol, filamental, and filamentone. Several of these compounds elicited antennal responses in pollinating (Tegeticula) and non-pollinating (Prodoxus) moth species upon stimulation in electrophysiol. recordings. In addition, synthetic (Z)-filamentolide attracted significant numbers of both sexes of two associated Prodoxus species in a field trapping experiment Highly specialized insect-plant interactions, such as obligate pollination mutualisms, are predicted to be maintained through “”private channels”” dictated by specific compounds The identification of novel bioactive tetranorsesquiterpenoids is a first step in testing such a hypothesis in the Yucca-yucca moth interaction.

Journal of Chemical Ecology published new progress about Antenna (anatomical). 1530-33-2 belongs to class bromides-buliding-blocks, and the molecular formula is C21H22BrP, SDS of cas: 1530-33-2.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Mato, Mauro; Martin-Torres, Inmaculada; Herle, Bart; Echavarren, Antonio M. published the artcile< Cyclopropane-alkene metathesis by gold(I)-catalyzed decarbenation of persistent cyclopropanes>, Product Details of C21H22BrP, the main research area is disubstituted cyclopropane diastereoselective preparation; cyclopropane alkene metathesis gold catalyzed.

A gold(I)-catalyzed cyclopropane-alkene metathesis was demonstrated with two new families of cyclopropane derivatives of naphthalene I [R1 = H, Me, Ph; R2 = H, Me, Ph; R1R2 = (CH2)5]/(exo)-1-phenyl-1a,7b-dihydro-1H-cyclopropa[a]naphthalene and phenanthrene II [Ar = C6H5, 4-MeOC6H4, 3,5-di-MeC6H3]. In this process, metal carbene units are transferred from a persistent cyclopropane to an alkene, upon release of naphthalene or phenanthrene, allowing the diastereoselective synthesis of a wide range of aryl and vinyl cyclopropanes III [R = 3-MeC6H4, 4-ClC6H4, 4-CF3C6H4] and IV [R = C6H5, 3-BrC6H4, 4-OAcC6H4, etc.] resp.

Organic & Biomolecular Chemistry published new progress about Cyclopropanation catalysts, stereoselective. 1530-33-2 belongs to class bromides-buliding-blocks, and the molecular formula is C21H22BrP, Product Details of C21H22BrP.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Kraszewski, Karol; Tomczyk, Ireneusz; Drabinska, Aneta; Bienkowski, Krzysztof; Solarska, Renata; Kalek, Marcin published the artcile< Mechanism of Iodine(III)-Promoted Oxidative Dearomatizing Hydroxylation of Phenols: Evidence for a Radical-Chain Pathway>, Synthetic Route of 1530-33-2, the main research area is phenol iodine oxidative dearomatization kinetics mechanism; hypervalent iodine; mechanistic investigations; phenol dearomatization; radical-chain pathway; synthetic methods.

The oxidative dearomatization of phenols with the addition of nucleophiles to the aromatic ring induced by hypervalent iodine(III) reagents and catalysts has emerged as a highly useful synthetic approach. However, exptl. mechanistic studies of this important process have been extremely scarce. In this report, we describe systematic investigations of the dearomatizing hydroxylation of phenols using an array of exptl. techniques. Kinetics, EPR spectroscopy, and reactions with radical probes demonstrate that the transformation proceeds by a radical-chain mechanism, with a phenoxyl radical being the key chain-carrying intermediate. Moreover, UV and NMR spectroscopy, high-resolution mass spectrometry, and cyclic voltammetry show that before reacting with the phenoxyl radical, the water mol. becomes activated by the interaction with the iodine(III) center, causing the Umpolung of this formally nucleophilic substrate. The radical-chain mechanism allows the rationalization of all existing observations regarding the iodine(III)-promoted oxidative dearomatization of phenols.

Chemistry – A European Journal published new progress about Activation entropy. 1530-33-2 belongs to class bromides-buliding-blocks, and the molecular formula is C21H22BrP, Synthetic Route of 1530-33-2.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Ning, Shulin; Zheng, Lianyou; Bai, Ya; Wang, Shutao; Wang, Siyu; Shi, Lingling; Gao, Qiansong; Che, Xin; Zhang, Zhuoqi; Xiang, Jinbao published the artcile< Highly selective electroreductive linear dimerization of electron-deficient vinylarenes>, Formula: C21H22BrP, the main research area is diaryl butane preparation; vinylarene preparation regioselective electroreductive dimerization.

A direct electroreductive dimerization of electron-deficient vinylarenes R1R2C:CR3R4 (R1 = Ph, 4-NCC6H4, pyridin-4-yl, etc., R2 = R3 = R4 = H; R1 = 4-EtO2CC6H4, R2 = Me, Ph, R3 = R4 = H; R1 = 4-MeO2CC6H4, R2 = H, R3 = Me, R4 = H, Me; etc.) for the synthesis of 1,4-diarylbutanes R1R2CH-CR3R4-CR3R4-CHR1R2 as been developed using a simple undivided cell with inexpensive carbon electrodes at room temperature The control and deuterium-labeling experiments of electroreductive dimerization suggest that the hydrogen source comes from the solvent CH3CN. This protocol provides a mild and efficient route for the construction of C-C bond in moderate to good yields with high regioselectivity and broad substrate scope.

Tetrahedron published new progress about Alkylarenes Role: SPN (Synthetic Preparation), PREP (Preparation). 1530-33-2 belongs to class bromides-buliding-blocks, and the molecular formula is C21H22BrP, Formula: C21H22BrP.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Tyler, Jasper L.; Noble, Adam; Aggarwal, Varinder K. published the artcile< Strain-Release-Driven Friedel-Crafts Spirocyclization of Azabicyclo[1.1.0]butanes>, Recommanded Product: Isopropyltriphenylphosphonium bromide, the main research area is tertiary butoxy carbonyl azetidino spiro tetralin preparation regioselective DFT; alkylazetidine preparation Friedel Crafts spirocyclization tetrafluoroboric acid etherate catalyst; azabicyclobutane carbinol preparation alkyl halide alkylation; azabicylo[1.1.0]butanes; azetidines; dearomatization; spiro compounds; strained molecules.

The strain-release-driven Friedel-Crafts spirocyclization of azabicyclo[1.1.0]butane-tethered (hetero)aryls I (R = H, Me, Bn, allyl, triethylsilyl; R1 = Ph, 2-naphthyl, benzothiophen-2-yl, etc.) for the synthesis of a unique library of azetidine spiro-tetralins e.g., II was reported. The reaction was discovered to proceed through an unexpected interrupted Friedel-Crafts mechanism, generating a highly complex azabicyclo[2.1.1]hexane scaffold. This dearomatized intermediate, formed exclusively as a single diastereomer, can be subsequently converted to the Friedel-Crafts product upon electrophilic activation of the tertiary amine, or trapped as a Diels-Alder adduct in one-pot. The rapid assembly of mol. complexity demonstrated in these reactions highlights the potential of the strain-release-driven spirocyclization strategy to be utilized in the synthesis of medicinally relevant scaffolds.

Angewandte Chemie, International Edition published new progress about Aldehydes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 1530-33-2 belongs to class bromides-buliding-blocks, and the molecular formula is C21H22BrP, Recommanded Product: Isopropyltriphenylphosphonium bromide.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Jagot, Fatema; Ntsimango, Songeziwe; Ngwira, Kennedy J.; Fernandes, Manuel A.; de Koning, Charles B. published the artcile< Synthesis of Angucycline/Tetrangulol Derivatives Using Suzuki-Miyaura Cross-Coupling and Ring-Closing Carbonyl-Olefin Metathesis Reactions>, Electric Literature of 1530-33-2, the main research area is angucycline tetrangulol preparation.

Key steps in the synthesis of derivatives of the angucycline, tetrangulol include the use of a palladium catalyzed Suzuki-Miyaura cross-coupling reaction for the assembly of I from 2-iodo-3-methoxy-5-methylbenzaldehyde and II. The biaryl product I was then subjected to an iron-catalyzed ring-closing carbonyl-olefin metathesis reaction to afford 1,7,12-trimethoxy-3-methyltetraphene, which was oxidized to the corresponding quinone III. Late stage oxidation of the quinone III with Ru[Cl2(p-cymene)]2 and an oxidant unexpectedly afforded the chlorinated compounds IV (R = H, OH).

European Journal of Organic Chemistry published new progress about Anthracyclines Role: SPN (Synthetic Preparation), PREP (Preparation). 1530-33-2 belongs to class bromides-buliding-blocks, and the molecular formula is C21H22BrP, Electric Literature of 1530-33-2.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Brandstatter, Marco; Huwyler, Nikolas; Carreira, Erick M. published the artcile< Gold(I)-catalyzed stereoselective cyclization of 1,3-enyne aldehydes by a 1,3-acyloxy migration/Nazarov cyclization/aldol addition cascade>, COA of Formula: C21H22BrP, the main research area is bicyclooctenone preparation diastereoselective enantioselective; enyne aldehyde propargylic acetate preparation cyclization tandem gold catalyst.

Stereoselective synthesis of bicyclo[3.3.0]octenones I (R = Ph, naphthalen-2-yl, i-Pr, etc.) from chiral 1,3-enyne aldehydes bearing propargylic acetates (R,E/Z)-CH3CH(OC(O)CH3)CCC(R)=CH(CH2)2CHO is described. The method is based on a Au(I)-catalyzed domino sequence with concomitant transfer of chirality involving 1,3-acyloxy migration followed by Nazarov cyclization and an unprecedented aldol addition The method furnishes densely functionalized bicyclic structures in high yields, with up to 97% ee and good diastereoselectivity.

Chemical Science published new progress about Aldol addition catalysts, stereoselective. 1530-33-2 belongs to class bromides-buliding-blocks, and the molecular formula is C21H22BrP, COA of Formula: C21H22BrP.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Huang, Zhiliang; Guan, Renpeng; Shanmugam, Muralidharan; Bennett, Elliot L.; Robertson, Craig M.; Brookfield, Adam; McInnes, Eric J. L.; Xiao, Jianliang published the artcile< Oxidative Cleavage of Alkenes by O2 with a Non-Heme Manganese Catalyst>, Application of C21H22BrP, the main research area is alkene oxygen light manganese oxidation catalyst; ketone preparation.

The oxidative cleavage of C=C double bonds with mol. oxygen to produce carbonyl compounds is an important transformation in chem. and pharmaceutical synthesis. In nature, enzymes containing the first-row transition metals, particularly heme and non-heme iron-dependent enzymes, readily activate O2 and oxidatively cleave C=C bonds with exquisite precision under ambient conditions. The reaction remains challenging for synthetic chemists, however. There are only a small number of known synthetic metal catalysts that allow for the oxidative cleavage of alkenes at an atm. pressure of O2, with very few known to catalyze the cleavage of nonactivated alkenes. In this work, we describe a light-driven, Mn-catalyzed protocol for the selective oxidation of alkenes to carbonyls under 1 atm of O2. For the first time, aromatic as well as various nonactivated aliphatic alkenes could be oxidized to afford ketones and aldehydes under clean, mild conditions with a first row, biorelevant metal catalyst. Moreover, the protocol shows a very good functional group tolerance. Mechanistic investigation suggests that Mn-oxo species, including an asym., mixed-valent bis(μ-oxo)-Mn(III,IV) complex, are involved in the oxidation, and the solvent methanol participates in O2 activation that leads to the formation of the oxo species.

Journal of the American Chemical Society published new progress about Aldehydes Role: SPN (Synthetic Preparation), PREP (Preparation). 1530-33-2 belongs to class bromides-buliding-blocks, and the molecular formula is C21H22BrP, Application of C21H22BrP.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Ge, Liang; Wang, Ding-Xing; Xing, Renyi; Ma, Di; Walsh, Patrick J.; Feng, Chao published the artcile< Photoredox-catalyzed oxo-amination of aryl cyclopropanes>, Application of C21H22BrP, the main research area is aryl cyclopropane azole iridium photocatalyst ring opening oxidative amination; azolylalkyl ketone regioselective preparation.

A photoredox-coupled ring-opening oxo-amination of electronically unbiased cyclopropanes, which enabled the expedient construction of a host of structurally diverse β-amino ketone derivatives Through one electron oxidation, the relatively inert aryl cyclopropanes were readily converted into reactive radical cation intermediates, which in turn participate in the ensuing ring-opening functionalizations. Based on mechanistic studies, the present oxo-amination was proposed to proceed through an SN2-like nucleophilic attack/ring-opening manifold. This protocol featured wide substrate scope, mild reaction conditions, and use of dioxygen as an oxidant both for catalyst regeneration and oxygen-incorporation. Moreover, a one-pot formal aminoacylation of olefins was described through a sequential cyclopropanation/oxo-amination.

Nature Communications published new progress about Aminoacylation (regioselective). 1530-33-2 belongs to class bromides-buliding-blocks, and the molecular formula is C21H22BrP, Application of C21H22BrP.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Zhu, Jun; Zhang, Rui; Dong, Guangbin published the artcile< Orthogonal cross-coupling through intermolecular metathesis of unstrained C(aryl)-C(aryl) single bonds>, Electric Literature of 1530-33-2, the main research area is biaryl ruthenium catalyst regioselective orthogonal cross coupling reaction.

Ruthenium-catalyzed reversible C-C single-bond metathesis reaction that allowed redox- and pH-neutral biaryl synthesis. Assisted by directing groups, unstrained homo-biaryl compounds underwent aryl exchanges to generate cross-biaryl products, catalyzed by a well-defined air-stable ruthenium(II) complex. Functional groups reactive under typical cross-coupling reactions, such as halogen, silyl and boronate moieties, were compatible under the metathesis conditions. Mechanistic studies disclosed an intriguing ‘olefin-metathesis-like’ pathway that involved an unexpected heptacoordinated, 18-electron closed-shell intermediate. The distinct reaction mode discovered here is expected to inspire the development of more general C-C single-bond metathesis and orthogonal cross-coupling reactions.

Nature Chemistry published new progress about Biaryls Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 1530-33-2 belongs to class bromides-buliding-blocks, and the molecular formula is C21H22BrP, Electric Literature of 1530-33-2.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary