Category: 81216-14-0

Bauer, Adriano published the artcileChemoselective formal β-functionalization of substituted aliphatic amides enabled by a facile stereoselective oxidation event, Safety of 7-Bromohept-1-yne, the publication is Chemical Science (2019), 10(42), 9836-9840, database is CAplus and MEDLINE.

A facile and stereoselective dehydrogenation event enabling the functionalization of aliphatic amides, e.g., 1-(indolin-1-yl)-2-methylpropan-1-one at different positions in a one-pot fashion has been described. Derivatives of relevant pharmaceuticals were formally functionalized in the β-position in late-stage manner. A single-step synthesis of incrustoporine from a simple precursor further showcases the potential utility of this approach.

Chemical Science published new progress about 81216-14-0. 81216-14-0 belongs to bromides-buliding-blocks, auxiliary class Linker,PROTAC Linker, name is 7-Bromohept-1-yne, and the molecular formula is C7H11Br, Safety of 7-Bromohept-1-yne.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Bielefeld, Jens published the artcileHydroaminoalkylation of Allenes, Related Products of bromides-buliding-blocks, the publication is Synlett (2019), 30(8), 967-971, database is CAplus.

The first examples of early-transition-metal-catalyzed hydroaminoalkylation reactions of allenes are reported. Initial studies performed with secondary aminoallenes led to the identification of a suitable titanium catalyst and revealed that under the reaction conditions, the initially formed hydroaminoalkylation products undergo an unexpected titanium-catalyzed rearrangement to form the thermodynamically more stable allylamines. The assumption that this rearrangement involves a reactive allylic cation intermediate provides a simple explanation of the fact that no successful early-transition-metal-catalyzed hydroaminoalkylations of allenes have previously been reported. As a result of the generation of the corresponding cation, the titanium-catalyzed intermol. hydroaminoalkylation of propa-1,2-diene unexpectedly gives an aminocyclopentane product formed by incorporation of two equivalent of propa-1,2-diene.

Synlett published new progress about 81216-14-0. 81216-14-0 belongs to bromides-buliding-blocks, auxiliary class Linker,PROTAC Linker, name is 7-Bromohept-1-yne, and the molecular formula is C7H11Br, Related Products of bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Wilkinson, Andrew A. published the artcileSite-Selective and Rewritable Labeling of DNA through Enzymatic, Reversible, and Click Chemistries, Recommanded Product: 7-Bromohept-1-yne, the publication is ACS Central Science (2020), 6(4), 525-534, database is CAplus and MEDLINE.

Current methods for bioconjugation rely on the introduction of stable linkers that lack the required versatility to perform sequential functionalizations. However, sequential manipulations are an increasing requirement in chem. biol. because they can underpin multiple analyses of the same sample to provide a wider understanding of cell behavior. Here, we present a new method to site-selectively write, remove, and rewrite chem. functionality to a biomol., DNA in this case. Our method combines the precision and robustness of methyltransferase-directed labeling with the reversibility of acyl hydrazones and the efficiency of click chem. Underpinning the method is a new S-adenosyl-L-methionine derivative to site-selectively label DNA with a bifunctional chem. handle containing an acyl hydrazone-linker and a terminal azide. Functional tags are conjugated via the azide and can be removed (i.e., untagged) when needed at the acyl hydrazone via exchange with hydroxyl amine. The formed hydrazide-labeled DNA is a versatile intermediate that can be either rewritten to reset the original chem. handle or covalently reacted with a permanent tag. This ability to write, tag, untag, and permanently tag DNA is exploited to sequentially introduce two fluorescent dyes on DNA. Finally, we demonstrate the potential of the method by developing a protocol to sort labeled DNA using magnetic beads, with subsequent amplification of the sorted DNA sample for further anal. The presented method opens new avenues for site-selective bioconjugation and should underpin integrative approaches in chem. biol. where sequential functionalizations of the same sample are required. We present a method using MTases, acyl hydrazone, and click chem. to site-selectively tag, untag, and rewrite on DNA. Sequential labeling of DNA or sorting PCR DNA demonstrate its versatility.

ACS Central Science published new progress about 81216-14-0. 81216-14-0 belongs to bromides-buliding-blocks, auxiliary class Linker,PROTAC Linker, name is 7-Bromohept-1-yne, and the molecular formula is C15H14BNO4S, Recommanded Product: 7-Bromohept-1-yne.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Yang, Xu-Heng published the artcileCopper-catalyzed alkynylation/annulation cascades of N-allyl ynamides: regioselective access to medium-sized N-heterocycles, Recommanded Product: 7-Bromohept-1-yne, the publication is Organic Chemistry Frontiers (2021), 8(1), 18-24, database is CAplus.

A synthetic strategy based on sequential application of aza-Claisen rearrangement, C-H functionalization, C-N coupling and cyclization as key steps has been developed for the synthesis of various medium-sized N-heterocycles of pharmaceutical relevance. This efficient new method exhibits a broad scope and provides a highly efficient synthesis of N-heterocycles I [R¹ = (4-methylbenzene)sulfonyl, naphthalene-2-sulfonyl, thiophene-2-sulfonyl, etc.; R² = H, Me; R³ = C₆H₅, 4-ClC₆H₄, thien-2-yl, etc.; R⁴ = H, Me; X = (CH₂)_n; n = 0, 1, 2, 3] of different ring sizes (6-, 7-, and 8-membered rings) in moderate to good yields.

Organic Chemistry Frontiers published new progress about 81216-14-0. 81216-14-0 belongs to bromides-buliding-blocks, auxiliary class Linker,PROTAC Linker, name is 7-Bromohept-1-yne, and the molecular formula is C7H15NO, Recommanded Product: 7-Bromohept-1-yne.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Tirpak, Michael R. published the artcileReaction of dicobalt octacarbonyl with some acetylenic compounds, COA of Formula: C7H11Br, the publication is Journal of Organic Chemistry (1960), 687-90, database is CAplus.

In a recent investigation (CA 50, 12809i), it was reported that Co₂(CO)₈ reacted with RCCR’ (I) according to the reaction: I + Co₂(CO)₈ → RC₂R’Co₂(CO)₆ + 2CO. In the present study the effect of various groups (R and R’) upon the rate of reaction was determined The relative reactivities of various I were determined from the half-lives of their reactions. The half-lives were obtained from a plot of volume of evolved CO vs. time. The half-life of the reaction with BuCCH (II) was assigned a value of 100 on the relative reactivity scale and the relative reactivity of each of the I was calculated from: relative reactivity = t_1/2 II/t_1/2 I × 100. The average half-life for II was found to be 320 sec. The differences in the relative reactivities were not great; however, CO₂H, CO₂Me, and CH₂OH groups appeared to enhance the reactivity when attached to the triple bonded C. An anomalous behavior of certain propargyl-type halides was found and was attributed to a possible coupling reaction of these halides in the presence of Co₂(CO)₈. The following I (general methods of their preparation were given) were prepared and their relative reactivities determined (R, R’, b.p./mm., n_D/temperature, d₄/temperature, relative reactivity given): Bu, H, 70.5°/atm., 1.3970/24°, 0.7137/26°, 100; Bu, D, 70-4°/atm., 1.3970/23°, 0.722/22°, 105; Pr, Me, 82-8°/760, 1.4127/24°, 0.7401/20°, 60; Et, Et, 79-80°/760, 1.4101/23°, 0.7231/20°, 98; tert-Bu, H, 35-6°/760, 1.3743/21°, 0.6683/20°, 88; Me, Me, 29°/760, 1.3880/27°, 0.6913/20°, 56; CH₂:CMe, H, 32.5°/760, 1.4148/21°, 0.695/25°, 119; HCC(CH₂)₄, H, 32.5-3.5°/55, 1.4454/21°, 0.8195/24°, 81; Ph, H, 44-5°/22, 1.5488/22°, 0.9283/22°, 114; o-tolyl, H, 42-4°/6, 1.5460/21°, 0.9224/24°, 78; m-tolyl, H, 62-4°/18, 1.5427/21°, 0.9073/26°, 110; p-tolyl, H, 61-2°/20, 1.5455/24°, 0.9159/20°, 112; 2,4-Me₂C₆H₃, H, 69-71°/9, 1.5451/25°, 0.930/23°, 88; 2,5-Me₂C₆H₃, H, 49°/2, 1.5412/24°, 0.9180/21°, 88; 3,4-Me₂C₆H₃, H, 59-62°/3, 1.5494/25°, 0.9246/24°, 115; 2,4,6-Me₃C₆H₂, H, 62-3°/2.5, 1.5440/25°, 0.9185/25°, 20; 2,6,4-Me₂(tert-Bu)C₆H₂, H, 88-90°/2, 1.5313/23°, 0.9018/22°, 23; Ph, Ph, 150°/8 (m. 58-60°), -, -, 60; Bu, CO₂H, 116°/7, 1.4607/23, 0.9775/23°, 160; Et, (CH₂)₃CO₂H, 126-7°/8, 1.4543/28° 0.9762/28°, 60; Ph, CO₂H, -(m. 135-7°), -, -, 226; H, CH₂OH, 111-12°/atm., 1.4312/22°, 0.9338/24°, 194; H, CMe₂OH, 103°/atm., 1.4204/24°, 0.8518/28°, 177; Bu, CH₂OH, 77-8°/4, 1.4520/30°, 0.8810/28°, 120; Bu, CHMeOH, 67-9°/8, 1.4468/23°, 0.8747/24°, 123; tert-Bu, CH₂OH, 68-9°/17, 1.4421/24°, 0.8600/23°, 89; Am, CO₂Me, 96°/12, 1.4460/23, 0.9260/22, 152; Et, (CH₂)₃CO₂Me, 85-6°/9, 1.4447/21°, 0.9365/21°, 68; Me, (CH₂)₄CO₂Me, 94°/13, 1.4470/22°, 0.9552/23°, 55; H, (CH₂)₅CO₂Me, 85-6°/10, 1.4403/23°, 0.9428/24°, 92; H, OBu, 40-1°/65, 1.4000/29°, 0.8161/29°, 1; H, CH₂OMe, 60.0-60.5°/760, 1.3948/23°, 0.8410/23°, 177; H, CH₂OCPh₃, -(m. 110.5-11.0°), -, -, 186; H, 2-tetrahydropyranyloxymethyl, 57.5-8.0°/7, 1.4573/21°, 1.0148/21°, 201; H, (CH₂)₅Br, 76.5-7.0°/18, 1.4773/22°, 1.2342/22°, 87; H, (CH₂)₄I, 62-3°/8, 1.5260/28°, 1.5822/26°, 86; H, C₆H₄F-p, -(m. 25-7°), -, -, 92; H, C₆H₄Cl-p, -(m. 43.0-4.5°), -, -, 90; H, C₆H₄Cl-m, 58-60°/9, 1.5630/23°, 1.116/25°, 102; H, C₆H₄Cl-o, 65-6°/12, 1.5694/25°, 1.1249/25°, 102; H, C₆H₄Br-p, -(m. 64.5-6.0°), -, -, 100; H, CH₂Cl, 55.5°/760, 1.4335/22°, 1.0385/23°, 172; H, CH₂Br, 82°/760, 1.4928/22°, 1.5775/22°, 385; H, CMe₂Cl, 74°/760, 1.4160/25°, 0.9085/25°, 178; Bu, CH₂Cl, 56-7°/10, 1.4585/25°, 0.9470/25°, 91; Bu, CH₂Br, 64-5°/8, 1.4910/22°, 1.2427/22°, 315; Bu, CH₂I, 78-9°/7, 1.5387/25°, 1.4914/23°, 476; BrCH₂, CH₂Br, 81-2°/7, 1.5844/30°, 2.0237/29°, 325.

Journal of Organic Chemistry published new progress about 81216-14-0. 81216-14-0 belongs to bromides-buliding-blocks, auxiliary class Linker,PROTAC Linker, name is 7-Bromohept-1-yne, and the molecular formula is C9H11BO3, COA of Formula: C7H11Br.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Mailig, Melrose published the artcileCatalytic Anti-Markovnikov Hydroallylation of Terminal and Functionalized Internal Alkynes: Synthesis of Skipped Dienes and Trisubstituted Alkenes, Name: 7-Bromohept-1-yne, the publication is Journal of the American Chemical Society (2017), 139(20), 6969-6977, database is CAplus and MEDLINE.

We have developed catalytic anti-Markovnikov hydroallylation of terminal and functionalized internal alkynes. In this article, we describe the development of the reaction, exploration of the substrate scope, and a study of the reaction mechanism. Synthesis of skipped dienes through the hydroallylation of terminal alkyl and aryl alkynes with simple allyl phosphates and 2-substituted allyl phosphates is described. The hydroallylation of functionalized internal alkynes leads to the formation of skipped dienes containing trisubstituted alkenes. We demonstrate that the hydroallylation of internal alkynes can be used in the regio- and diastereoselective synthesis of complex trisubstituted alkenes. A mechanism of the hydroallylation reaction is proposed, and exptl. evidence is provided for the key steps of the catalytic cycle. Stoichiometric experiments demonstrate an unexpected role of lithium alkoxide in the carbon-carbon bond-forming step of the reaction. A study of the hydrocupration of internal alkynes provides new insight into the structure, stability, and reactivity of alkenyl copper intermediates, as well as insight into the source of the regioselectivity in reactions of internal alkynes.

Journal of the American Chemical Society published new progress about 81216-14-0. 81216-14-0 belongs to bromides-buliding-blocks, auxiliary class Linker,PROTAC Linker, name is 7-Bromohept-1-yne, and the molecular formula is C7H11Br, Name: 7-Bromohept-1-yne.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Xu, Zi-Yang published the artcilePhotocatalytic Chemodivergent Synthesis of α-gem-Dihalovinyl Ketones and Chromen-2-Ones from Monoalkynes, Formula: C7H11Br, the publication is Advanced Synthesis & Catalysis (2022), 364(15), 2666-2672, database is CAplus.

A general photocatalytic substrate-controlled chemodivergent strategy starting from monoalkynes with polyhalomethanes such as BrCCl₃ and CBr₄ was developed, enabling Kharasch-type addition/nucleophilic substitution cascade to selectively produce α-gem-dihalovinyl ketones and chromen-2-ones with moderate to good yields. Use of monoalkynes without addnl. nucleophilic sites furnished α-gem-dihalovinyl ketones through a Kharasch-type addition and intermol. allylic substitution cascade whereas the latter transformation of 2-ethynylphenols allowed the full breaking of carbon-halogen bonds of BrCX₃ to access functionalized chromen-2-ones. The late-stage application of these resulting α-gem-dihalovinyl ketones demonstrates the versatility of their derivatization.

Advanced Synthesis & Catalysis published new progress about 81216-14-0. 81216-14-0 belongs to bromides-buliding-blocks, auxiliary class Linker,PROTAC Linker, name is 7-Bromohept-1-yne, and the molecular formula is C8H8O3, Formula: C7H11Br.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Armstrong, Megan K. published the artcileDifferential Dihydrofunctionalization of Terminal Alkynes: Synthesis of Benzylic Alkyl Boronates through Reductive Three-Component Coupling, Formula: C7H11Br, the publication is Journal of the American Chemical Society (2019), 141(15), 6173-6179, database is CAplus and MEDLINE.

The differential dihydrofunctionalization of terminal alkynes is accomplished through the reductive three-component coupling of terminal alkynes, aryl halides, and pinacolborane. The transformation results in hydrofunctionalization of both π-bonds of an alkyne in a single reaction promoted by cooperative action of a Cu/Pd catalyst system. The differential dihydrofunctionalization reaction has excellent substrate scope and can be accomplished in the presence of esters, nitriles, alkyl halides, epoxides, acetals, alkenes, aryl halides, and silyl ethers. Mechanistic experiments indicate that the reaction proceeds through Cu-catalyzed hydroboration followed by a 2nd hydrocupration. The resulting heterobimetallic complex is the key intermediate that participates in the subsequent Pd-catalyzed cross-coupling, which furnishes benzylic alkyl boronate products.

Journal of the American Chemical Society published new progress about 81216-14-0. 81216-14-0 belongs to bromides-buliding-blocks, auxiliary class Linker,PROTAC Linker, name is 7-Bromohept-1-yne, and the molecular formula is C7H11Br, Formula: C7H11Br.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Armstrong, Megan K. published the artcileDiastereodivergent Reductive Cross Coupling of Alkynes through Tandem Catalysis: Z- and E-Selective Hydroarylation of Terminal Alkynes, Category: bromides-buliding-blocks, the publication is Journal of the American Chemical Society (2018), 140(32), 10233-10241, database is CAplus and MEDLINE.

A diastereodivergent hydroarylation of terminal alkynes is accomplished using tandem catalysis. The hydroarylation allows highly selective synthesis of both E and Z diastereoisomers of aryl alkenes, from the same set of starting materials, using the same combination of palladium and copper catalysts. The selectivity is controlled by simple changes in the stoichiometry of the alc. additive. The hydroarylation has excellent substrate scope and can be accomplished in the presence of various classes of compounds, including esters, nitriles, alkyl halides, epoxides, carbamates, acetals, ethers, silyl ethers, and thioethers. The Z-selective hydroarylation is accomplished using a new approach based on tandem Sonogashira coupling and catalytic semiredn. The E-selective hydroarylation involves an addnl. catalytic isomerization of the Z-alkene. Our explorations of the reaction mechanism explain the role of individual reaction components and how the subtle changes in the reaction conditions influence the rates of specific steps of the hydroarylation. Our studies also show that, although the Z- and E-selective hydroarylation reactions are mechanistically closely related, the roles of the palladium and copper catalysts in the two reactions are different.

Journal of the American Chemical Society published new progress about 81216-14-0. 81216-14-0 belongs to bromides-buliding-blocks, auxiliary class Linker,PROTAC Linker, name is 7-Bromohept-1-yne, and the molecular formula is C7H11Br, Category: bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Lee, Mitchell T. published the artcileSynthesis of Isomerically Pure (Z)-Alkenes from Terminal Alkynes and Terminal Alkenes: Silver-Catalyzed Hydroalkylation of Alkynes, Application of 7-Bromohept-1-yne, the publication is Journal of the American Chemical Society (2019), 141(43), 17086-17091, database is CAplus and MEDLINE.

Here, an efficient synthesis of diastereopure Z-alkenes (Z:E > 300:1) through a silver-catalyzed hydroalkylation of terminal alkynes using alkylboranes as coupling partners is demonstrated. The exploration of the substrate scope, which reveals the broad functional group compatibility of the new method, is also described. Preliminary mechanistic studies suggest that a 1,2-metalate rearrangement of the silver borate intermediate is the key step responsible for the stereochem. outcome of the reaction.

Journal of the American Chemical Society published new progress about 81216-14-0. 81216-14-0 belongs to bromides-buliding-blocks, auxiliary class Linker,PROTAC Linker, name is 7-Bromohept-1-yne, and the molecular formula is C7H11Br, Application of 7-Bromohept-1-yne.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary