Tag: 100-200

Alkyl ether and enol analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth, Agrotis segetum: probing a proposed bioactive conformation for chain-elongated analogs was written by Gustavsson, Anna-Lena;Liljefors, Tommy;Hansson, Bill S.. And the article was included in Journal of Chemical Ecology in 1995.Reference of 4457-67-4 This article mentions the following:

To test a previous conclusion that chain-elongated analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth, Agrotis segetum, adopt a loop conformation of the terminal alkyl chain in the bioactive conformation, a series of alkyl ether and enol ether analogs of 1 and (Z)-5-dodecenyl acetate have been synthesized and tested using single-cell electrophysiol. In these analogs a methylene group in positions 7 and 9 of (Z)-5-decenyl acetate and in positions 7 and 11 in (Z)-5-dodecenyl acetate have been replaced by an oxygen atom to energetically facilitate the formation of a loop conformation in the chain-elongated analogs. The electrophysiol. results in conformation with mol. mechanisms (MM2 and MM3) calculated conformational energies show that the activity decreases of the chain-elongated ether analogs are significantly smaller than that for (Z)-5-dodecenyl acetate and that these activity decreases parallel the conformational energies for a loop formation of the terminal chains in the analogs. The results support the previous conclusion that the terminal chain of chain-elongated analogs of (Z)-5-decenyl acetate adopts a loop conformation in their bioactive conformations. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Reference of 4457-67-4).

1-Bromo-4-methoxybutane (cas: 4457-67-4) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. When the molecular ion is detected, the bromine and chlorine isotope patterns are very distinct, but caution is to be exercised for certain mixed chlorinated/brominated compounds, which can look similar to homohalogen patterns.Reference of 4457-67-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Organocatalytic Asymmetric Construction of Tetrasubstituted Carbon Stereocenters Bearing Three Heteroatoms via Intramolecular Cyclization of Vinylidene ortho-Quinone Methide with Imidates was written by Tian, Yuhong;Wu, Fengdi;Jia, Shiqi;Gong, Xiangnan;Mao, Hui;Wang, Pengfei;Qin, Wenling;Yan, Hailong. And the article was included in Organic Letters in 2022.Reference of 128-08-5 This article mentions the following:

Herein, an organocatalytic asym. protocol for the construction of naphtho[1′,2′:5,6][1,3]oxazino[3,4-a]indoles I (R¹ = H, F, Cl, Br, CF₃, R² = H; R¹ = H, R² = Cl, MeO; R³ = H, MeO, Et, Br, 4-i-PrC₆H₄, R⁴ = H; R³ = H, R⁴ = Br; R⁵ = Me, Et; R⁶ = Me, i-Pr, n-Pr, Ph) containing tetrasubstituted carbon stereocenters is reported. The reaction proceeds via the enantioselective intramol. cyclization reaction of vinylidene ortho-quinone methides with imidates to form pentacyclic heterocycles. The formed tetrasubstituted carbon center is stable at a high temperature and under the conditions for further transformations. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5Reference of 128-08-5).

1-Bromopyrrolidine-2,5-dione (cas: 128-08-5) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Reference of 128-08-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Manufacturing Process Development for Belzutifan, Part 1: A Concise Synthesis of the Indanone Starting Material was written by Peng, Feng;Tan, Lushi;Chen, Lu;Dalby, Stephen M.;DiRocco, Daniel A.;Duan, Jianjun;Feng, Minyi;Gong, Guan;Guo, Haiheng;Hethcox, J. Caleb;Jin, Lu;Johnson, Heather C.;Kim, Jungchul;Le, Diane;Lin, Yipeng;Liu, Wenjun;Shen, Jun;Wan, Yimei;Xiao, Chengqian;Xiang, Bangping;Xiang, Qun;Xu, Jing;Yan, Luliang;Yang, Weiyi;Ye, Honglin;Yu, Yanpei;Zhang, Jun. And the article was included in Organic Process Research & Development in 2022.Electric Literature of C4H4BrNO2 This article mentions the following:

A four-step synthesis of the indanone core of belzutifan (MK-6482) is described. This route starts from the commodity raw material dihydrocoumarin and was successfully demonstrated on a large scale to produce indanone 11 in the synthesis of belzutifan, an FDA-approved first-in-class therapy for the treatment of patients with certain types of Von Hippel-Lindau disease-associated tumors. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5Electric Literature of C4H4BrNO2).

1-Bromopyrrolidine-2,5-dione (cas: 128-08-5) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Electric Literature of C4H4BrNO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Efforts to Investigate the Effect of Planarizing the Triarylamine Geometry in Dyes for Dye-Sensitized Solar Cells was written by Almenningen, David Moe;Engh, Veslemoey Minge;Stroemsodd, Eivind Andreas;Hansen, Henrik Erring;Buene, Audun Formo;Hoff, Baard Helge;Gautun, Odd Reidar. And the article was included in ACS Omega in 2022.Safety of 1-Bromopyrrolidine-2,5-dione This article mentions the following:

The geometry of a dye for dye-sensitized solar cells (DSSCs) has a major impact on its optical and electronic properties. The dye structure also dictates the packing properties and how well the dye insulates the metal-oxide surface from oxidants in the electrolyte. The aim of this work is to investigate the effect of planarizing the geometry of the common triarylamine donor, frequently used in dyes for DSSC. Five novel dyes were designed and prepared; two employ conventional triarylamine donors with thiophene and furan π-spacers, two dyes have had their donors planarized through one sulfur bridge (making two distinct phenothiazine motifs), and the final dye has been planarized by forming a double phenoxazine. The synthesis of these model dyes proved to be quite challenging, and each required specially designed total syntheses. We demonstrate that the planarization of the triarylamine donor can have different effects. When planarization was achieved by a 3,7-phenothiazine and double phenoxazine structures, improved absorption properties were noted, and a panchromatic absorption was achieved by the latter. However, an incorrect linking of donor and acceptor moieties has the opposite effect. Further, electrochem. impedance spectroscopy revealed clear differences in charge recombination depending on the structure of the dye. A drawback of planarized dyes in relation to DSSC is their low oxidation potentials. The best photovoltaic performance was achieved by 3,7-phenothazine with furan as a π-spacer, which produces a power conversion efficiency of 5.2% (J_sc = 8.8 mA cm^-2, V_oc = 838 mV, FF = 0.70). In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5Safety of 1-Bromopyrrolidine-2,5-dione).

1-Bromopyrrolidine-2,5-dione (cas: 128-08-5) belongs to organobromine compounds. Many of the organo bromine compounds are relatively nonpolar. Bromine is more electronegative than carbon (2.8 vs 2.5) and hence the carbon in a carbon–bromine bond is electrophilic in nature. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Safety of 1-Bromopyrrolidine-2,5-dione

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Thiophene-Perylenediimide Bridged Dimeric Porphyrin Donors Based on the Donor-Acceptor-Donor Structure for Organic Photovoltaics was written by Piradi, Venkatesh;Gao, Yaxin;Yan, Feng;Imran, Muhammad;Zhao, Jianzhang;Zhu, Xunjin;So, Shu Kong. And the article was included in ACS Applied Energy Materials in 2022.COA of Formula: C4H4BrNO2 This article mentions the following:

Two D-A-D (D = donor, A = acceptor)-based small-mol. donors, TPDI-2P and F-TPDI-2P, are designed and synthesized for organic solar cells (OSCs), with two strong donor porphyrin units bridged by either an electron-deficient diethynyl-substituted thiophene-perylenediimide (TPDI) linker for the former or a diethynyl-fused TPDI linker for the latter; 3-ethylrhodanine units were then flanked sym. by phenylenethynylene π-linkers. Both compounds show strong absorption profiles from 400 to 800 nm, with a valley at 600 nm, attributed to the Soret and Q-bands of porphyrin units. Compared to TPDI-2P, F-TPDI-2P with a fused TPDI backbone exhibits high red shifted absorptions and low-lying energy levels due to increased coplanarity of the dimeric porphyrin units. As a result, the optimized photovoltaic device based on F-TPDI-2P/PC₇₁BM has a decent power conversion efficiency (PCE) of 8.21%, whereas the device TPDI-2P/PC₇₁BM has a slightly lower PCE (6.90%). The higher efficiency of F-TPDI-2P/PC₇₁BM is mainly due to better photocurrent generation and smoother surface morphol. with elevated charge carrier mobilities. The success of this mol. design strategy could be beneficial in the development of more efficient porphyrin-based donors for high-performance OSCs. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5COA of Formula: C4H4BrNO2).

1-Bromopyrrolidine-2,5-dione (cas: 128-08-5) belongs to organobromine compounds. Most of the natural organobromine compounds are produced by marine organisms, and several brominated metabolites with antibacterial, antitumor, antiviral, and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. COA of Formula: C4H4BrNO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Thiophane compounds. II was written by Karrer, P.;Schmid, H.. And the article was included in Helvetica Chimica Acta in 1944.Application of 4457-67-4 This article mentions the following:

The methyl-3-thiophanone described in the preceding abstract could have had the Me group in position 2 or 4. To elucidate this point, 2-methyl-3-thiophanone was synthesized by condensing HSCH₂CH₂CO₂Et (I) and MeCHBrCO₂Et (II), followed by cyclization and ketone cleavage. HSCH₂CH₂CO₂H (17.7 g.) was esterified with 200 cc. absolute alc. containing 1 cc. H₂SO₄, in a CO₂ atm., giving 17.7 g. I, b₂₀ 77.5°. To an ice-cold solution of 2.57 g. Na in 50 cc. absolute alc., 15 g. I was added, under N; the mixture was cooled to -15° and 20.3 g. II added dropwise with shaking. This mixture was shaken for 1 hr. at 15°, then heated to boiling for 1.5 hrs., then the alc. removed in vacuo, and the residue acidified with HCl. This was extracted with ether, washed with NaHCO₃, dried with Na₂SO₄ and the ether evaporated The resulting EtO₂CCH₂CH₂SCHMeCO₂Et (III) b_10.5 149-53°, was obtained in 82.5% yield. To 6.4 g. pulverized NaNH₂ in 70 cc. absolute ether was added about 1/4 of a solution of 19 g. III in 40 cc. absolute ether, with stirring, and the bath heated to 40-50° to initiate the reaction. The rest of the III was then added and stirring and refluxing continued for 3 hrs. This mixture was then allowed to stand overnight, decomposed with ice and 11 cc. AcOH, saturated with NaCl and extracted with ether. The ether solution was washed with NaHCO₃, dried, the ether evaporated and distilled The 2-methyl-4-carbethoxy-3-thiophanone (IV) so obtained in 48.5% yield, b₁₁ 123-30°, and in aqueous alc. solution gave a red-violet color with FeCl₃. Ketone cleavage of IV with 10% H₂SO₄ gave 2-methyl-3-thiophanone (81%), b₁₁, 90-100° (semicarbazone, m. 183-4°, gave a definite m.-p. lowering when mixed with the semicarbazone of the compound designated VII in the preceding abstract); hence the substance VII of the preceding abstract must be 4-methyl-3-thiophanone. The phenylhydrazone of the keto ester designated VI in the preceding abstract was fractionated into 2 fractions, A, m. 141.5-2.5°, and B, m. 167°, demonstrating that VI was a mixture in which the CO₂Et group was at positions 2 and 4. A was much more abundant than B. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Application of 4457-67-4).

1-Bromo-4-methoxybutane (cas: 4457-67-4) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.Application of 4457-67-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Discovery of N-(4-Aminobutyl)-N’-(2-methoxyethyl)guanidine as the First Selective, Nonamino Acid, Catalytic Site Inhibitor of Human Dimethylarginine Dimethylaminohydrolase-1 (hDDAH-1) was written by Lunk, Ina;Litty, Felix-Alexander;Hennig, Sven;Vetter, Ingrid R.;Kotthaus, Juerke;Altmann, Karin S.;Ott, Gudrun;Havemeyer, Antje;Garcia, Carmen Carrillo;Clement, Bernd;Schade, Dennis. And the article was included in Journal of Medicinal Chemistry in 2020.SDS of cas: 4457-67-4 This article mentions the following:

N-(4-Aminobutyl)-N’-(2-methoxyethyl)guanidine (8a) is a potent inhibitor targeting the hDDAH-1 active site (K_i = 18μM) and derived from a series of guanidine- and amidine-based inhibitors. Its nonamino acid nature leads to high selectivities toward other enzymes of the nitric oxide-modulating system. Crystallog. data of 8a-bound hDDAH-1 illuminated a unique binding mode. Together with its developed N-hydroxyguanidine prodrug 11, 8a will serve as a most widely applicable, pharmacol. tool to target DDAH-1-associated diseases. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4SDS of cas: 4457-67-4).

1-Bromo-4-methoxybutane (cas: 4457-67-4) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.SDS of cas: 4457-67-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Transition-Metal-Free Borylation of Alkyl Iodides via a Radical Mechanism was written by Liu, Qianyi;Hong, Junting;Sun, Beiqi;Bai, Guangcan;Li, Feng;Liu, Guoquan;Yang, Yang;Mo, Fanyang. And the article was included in Organic Letters in 2019.Reference of 4457-67-4 This article mentions the following:

The authors describe an operationally simple transition-metal-free borylation of alkyl iodides. This method uses com. available diboron reagents as the B source and exhibits excellent functional group compatibility. Also, a diverse range of primary and secondary alkyl iodides could be effectively transformed to the corresponding alkylboronates in excellent yield. Mechanistic studies suggest that this borylation reaction proceeds through a single-electron transfer mechanism featuring the generation of an alkyl radical intermediate. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Reference of 4457-67-4).

1-Bromo-4-methoxybutane (cas: 4457-67-4) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Reference of 4457-67-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Ni-catalyzed regio- and stereo-defined intermolecular cross-electrophile dialkylation of alkynes without directing group was written by Zhan, Yi-Zhou;Xiao, Nan;Shu, Wei. And the article was included in Nature Communications in 2021.Category: bromides-buliding-blocks This article mentions the following:

The nickel-catalyzed intermol. cross-dialkylation of alkynes devoid of directing or activating groups afforded multiple aliphatic substituted alkenes in a syn-selective fashion at room temp was reported. The combination of two-electron oxidative cyclometallation and single-electron cross-electrophile coupling of nickel enabled the syn-cross-dialkylation of alkynes at room temperature This reductive protocol enabled the sequential installation of two different alkyl substituents onto alkynes in a regio- and stereo-selective manner, circumvented the tedious preformation of sensitive organometallic reagents. The synthetic utility of this protocol was demonstrated by efficient synthesis of multi-substituted unfunctionalized alkenes and diverse transformations of the product. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Category: bromides-buliding-blocks).

1-Bromo-4-methoxybutane (cas: 4457-67-4) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Ni-Catalyzed Reductive 1,2-Cross-Dialkylation of Unactivated Alkenes with Two Alkyl Bromides was written by Zhang, Jian-Xin;Shu, Wei. And the article was included in Organic Letters in 2022.Reference of 4457-67-4 This article mentions the following:

Herein, a Ni-catalyzed reductive 1,2-dialkylation of unactivated aliphatic alkenes had been developed using two different alkyl bromides to gave (cyanoethyl)-alkyl-aryl-propanamides R¹CH₂CHR²CH₂C(O)NHAr [R¹ = cyanomethyl, H₂CCO₂Et, (2-oxotetrahydrofuran-3-yl); R² = Et, n-Pr, 3-phenylpropyl, etc.; Ar = Ph, 4-MeC₆H₄, 3-MeOC₆H₄, etc.]. The reaction proceeded smoothly under mild conditions to install two Csp³-Csp³ bonds onto directed aliphatic alkenes, demonstrating excellent chemo- and regioselectivity with good functional group tolerance. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Reference of 4457-67-4).

1-Bromo-4-methoxybutane (cas: 4457-67-4) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Reference of 4457-67-4

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary