Month: October 2022

《Transition-Metal-Free Borylation of Aryl Bromide Using a Simple Diboron Source》 was published in Journal of Organic Chemistry in 2020. These research results belong to Lim, Taeho; Ryoo, Jeong Yup; Han, Min Su. COA of Formula: C7H7BrO The article mentions the following:

The authors developed a simple and atom-economic transition-metal-free borylation reaction of aryl bromides. An atom-economic and com. available diboron source, bis-boronic acid (BBA), was used, and the borylation reaction was performed using a simple procedure at a mild temperature Under mild conditions, aryl bromides were converted to arylboronic acids directly without any deprotection steps, and the functional group tolerance was considerably high. The mechanism study suggested that this borylation reaction proceeds via a radical pathway. This simple borylation reaction will be useful for the synthesis of valuable arylboronic acids. The experimental process involved the reaction of 1-Bromo-3-methoxybenzene(cas: 2398-37-0COA of Formula: C7H7BrO)

1-Bromo-3-methoxybenzene(cas: 2398-37-0) is a compound useful in organic synthesis and other chemical processes. It is an intermediate used for pharmaceuticals, perfumes and agrochemicals.COA of Formula: C7H7BrO

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

《Metal-free synthesis of 3-chalcogenyl chromones from alkynyl aryl ketones and diorganyl diselenides/disulfides mediated by PIFA》 was published in Organic Chemistry Frontiers in 2020. These research results belong to Ai, Zhenkang; Xiao, Jiaxi; Li, Yadong; Guo, Boying; Du, Yunfei; Zhao, Kang. Reference of 1,2-Diphenyldisulfane The article mentions the following:

The 3-selenyl/sulfenyl chromones/thiochromones I (R = Ph, Me, 4-chlorophenyl, etc.; R1 = H, 7-Me, 6-Cl, 5-CF3, etc.; R2 = Ph, cyclopropyl, thiophen-3-yl, etc.) were conveniently synthesized from the PIFA-mediated reactions between alkynyl aryl ketones bearing an ortho-methoxy/methylthio group R1-2-XMe-C6H3C(O)CCR2 and diorganyl diselenides/disulfides RYYR (Y = Se/S). This metal-free approach is postulated to first undergo the formation of the reactive RSeOCOCF3 or RSOCOCF3 from the reaction of diorganyl diselenides or disulfides with PIFA, followed by the electrophilic cyclization of alkynyl aryl ketones enabled by the electrophilic species generated herein. In the part of experimental materials, we found many familiar compounds, such as 1,2-Diphenyldisulfane(cas: 882-33-7Reference of 1,2-Diphenyldisulfane)

1,2-Diphenyldisulfane(cas: 882-33-7) belongs to ethers.Oxygen is more electronegative than carbon, thus the alpha hydrogens of ethers are more acidic than those of simple hydrocarbons. Reference of 1,2-Diphenyldisulfane They are far less acidic than alpha hydrogens of carbonyl groups (such as in ketones or aldehydes), however.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

《Simultaneous determination of nine perfluoroalkyl carboxylic acids by a series of amide acetals derivatization and gas chromatography tandem mass spectrometry》 was written by Ji, Yongyan; Cui, Zongyan; Li, Xuemin; Wang, Zhibin; Zhang, Jinjie; Li, Adan. Category: ethers-buliding-blocks And the article was included in Journal of Chromatography A in 2020. The article conveys some information:

A novel and simple derivatization method using a series of amide acetals as derivatization reagents, along with gas chromatog. tandem mass spectrometry (GC-MS/MS) anal., were developed and validated for simultaneous determination of 9 perfluoroalkyl carboxylic acids (PFCAs) in this study. The structures and fragmentation pathway of PFCAs derivatives were deduced and verified. The derivatization method developed in this study improved the sensitivity of the detection of PFCAs by GC. The applicability of 6 amide acetals for the derivatization of PFCAs was demonstrated. Derivatization conditions for 9 PFCAs were optimized with addition of 20μL of derivatization reagent and reaction at 35°C for 30 min. 9 PFCAs derivatives were confirmed to be stable over 15 days. The instrument detection limits (IDLs) were lower than 0.01 pg/μL. The intra and inter-day precisions were below 4.06% and 5.48%, resp. To demonstrate the utility of the derivatization method, the level of PFCAs in the marine products were detected. The alk. digestion followed by solid-phase extraction (SPE) cleanup method was used for pretreatment. The method detection limits (MDLs) ranged from 0.04 to 0.10 ng/g, and the spiked recoveries ranged between 54.72% and 107.29%, with relative standard deviation (RSD) of 1.53%-11.89%. Five PFCAs were detected in the range of 0.66 to 499.03 ng/g dry weight The experimental process involved the reaction of N,N-Dimethylformamide Dimethyl Acetal(cas: 4637-24-5Category: ethers-buliding-blocks)

N,N-Dimethylformamide Dimethyl Acetal(cas: 4637-24-5) belongs to anime. Many important products require amines as part of their syntheses. Methylamine is utilized in the production of the analgesic meperidine (trade name Demerol) and the photographic developer Metol (trademark), and dimethylamine is used in the synthesis of the antihistamine diphenhydramine (trade name Benadryl), the solvent dimethylformamide (DMF), and the rocket propellant 1,1-dimethylhydrazine. The synthesis of the insect repellent N,N-diethyl-m-toluamide (DEET) incorporates diethylamine while that of the synthetic fibre Kevlar requires aromatic amines.Category: ethers-buliding-blocks

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Komkov, A. V.; Baranin, S. V.; Dmitrenok, A. S.; Kolotyrkina, N. G.; Zavarzin, I. V. published their research in Russian Chemical Bulletin in 2021. The article was titled 《A new route to the synthesis of 4-amino-substituted pyrido[2,3-d]pyrimidin-5-one derivatives》.Category: ethers-buliding-blocks The article contains the following contents:

The reaction of 6-(R-amino)-5-acetyl-4-methylsulfonyl-2-phenylpyrimidines with amines was studied. 6-Arylamino derivatives reacted with alkylamines to form 6-alkylamino-4-arylamino-5-acetyl-2-phenylpyrimidines, which upon refluxing in benzene with DMF dimethylacetal are converted to 4-alkylamino-8-aryl-2-phenylpyrido[2,3-d]pyrimidin-5(8H)-ones, e.g. I. The cyclization proceeded selectively with participation of the arylamino group only, the alkylamino group being not involved. At the same time, refluxing of 5-acetyl-4,6-dibenzylamino-2-phenylpyrimidine with DMF dimethylacetal in toluene affords the product of condensation on the acetyl group, which upon refluxing in o-xylene transforms to 4-benzylamino-8-benzyl-2-phenylpyrido[2,3-d]pyrimidin-5(8H)-one. In the experiment, the researchers used N,N-Dimethylformamide Dimethyl Acetal(cas: 4637-24-5Category: ethers-buliding-blocks)

N,N-Dimethylformamide Dimethyl Acetal(cas: 4637-24-5) belongs to anime. Many important products require amines as part of their syntheses. Methylamine is utilized in the production of the analgesic meperidine (trade name Demerol) and the photographic developer Metol (trademark), and dimethylamine is used in the synthesis of the antihistamine diphenhydramine (trade name Benadryl), the solvent dimethylformamide (DMF), and the rocket propellant 1,1-dimethylhydrazine. The synthesis of the insect repellent N,N-diethyl-m-toluamide (DEET) incorporates diethylamine while that of the synthetic fibre Kevlar requires aromatic amines.Category: ethers-buliding-blocks

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Cassiano, Chiara; Morretta, Elva; Costantini, Matteo; Fassi, Enrico M. A.; Colombo, Giorgio; Sattin, Sara; Casapullo, Agostino published their research in Bioorganic Chemistry in 2021. The article was titled 《Analysis of Hsp90 allosteric modulators interactome reveals a potential dual action mode involving mitochondrial MDH2》.Related Products of 139115-91-6 The article contains the following contents:

Hsp90 (i.e., Heat shock protein 90) is a well-established therapeutic target for several diseases, ranging from misfolding-related disfunctions to cancer. In this framework, we have developed in recent years a family of benzofuran compounds that act as Hsp90 allosteric modulators. Such mols. can interfere with the stability of some relevant Hsp90 client oncoproteins, showing a low μM cytotoxic activity in vitro in cancer cell lines. Here we identify the target profile of these chem. probes by means of chem. proteomics, which established MDH2 (mitochondrial malate dehydrogenase) as an addnl. relevant cellular target that might help elucidate the mol. mechanism of their citotoxicity. Western blotting, DARTS (i.e., Drug Affinity Responsive Target Stability) and enzymic assays data confirmed a dose-dependent interaction of MDH2 with several members of the benzofuran Hsp90 modulators family and a computational model allowed to interpret the observed interactions. After reading the article, we found that the author used tert-Butyl (2-(2-hydroxyethoxy)ethyl)carbamate(cas: 139115-91-6Related Products of 139115-91-6)

tert-Butyl (2-(2-hydroxyethoxy)ethyl)carbamate(cas: 139115-91-6) belongs to ethers.The C-O bonds that comprise simple ethers are strong. They are unreactive toward all but the strongest bases. Although generally of low chemical reactivity, they are more reactive than alkanes. Related Products of 139115-91-6

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Zhang, Chen; Ma, Na-Na; Yu, Zi-Lun; Shen, Chuanji; Zhou, Xiaocong; Chu, Xue-Qiang; Rao, Weidong; Shen, Zhi-Liang published their research in Organic Chemistry Frontiers in 2021. The article was titled 《Palladium-catalyzed direct reductive cross-coupling of aryltrimethylammonium salts with aryl bromides》.COA of Formula: C7H7BrO The article contains the following contents:

An efficient palladium-catalyzed direct reductive cross-coupling of aryltrimethylammonium salts with aryl bromides was developed. The reactions proceeded smoothly in the presence of a palladium catalyst, magnesium turnings, LiCl, and TMEDA in THF at room temperature, leading to the corresponding biaryl compounds in moderate to good yields with reasonable functional group tolerance. The one-pot reaction using cheap and readily available aryl bromide as a coupling partner were simple to handle, thereby avoiding the use of pre-prepared organometallic reagents. In the experiment, the researchers used many compounds, for example, 1-Bromo-3-methoxybenzene(cas: 2398-37-0COA of Formula: C7H7BrO)

1-Bromo-3-methoxybenzene(cas: 2398-37-0) is a compound useful in organic synthesis and other chemical processes. It is an intermediate used for pharmaceuticals, perfumes and agrochemicals.COA of Formula: C7H7BrO

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Bourque, Jeremy L.; Nanni, Robert A.; Biesinger, Mark C.; Baines, Kim M. published their research in Inorganic Chemistry in 2021. The article was titled 《Synthesis and Reactivity of Cationic Gallium(I) [12]Crown-4 Complexes》.Related Products of 33100-27-5 The article contains the following contents:

The synthesis and reactivity of a Ga(I) cationic complex using [12]crown-4 as a stabilizing ligand were explored. The synthesis of [Ga([12]crown-4)][GaCl4] was achieved in one step from com. available starting materials. Anion exchange was used to replace the reactive tetrachlorogallate anion for the perfluorophenylborate anion. [Ga([12]crown-4)][B(C6F5)4] was analyzed using XPS, which allowed for the classification of the Ga(I)-crown ether complex as electron-deficient. Reactions of the Ga(I)-crown ether complex with Cp*K and cryptand[2.2.2] demonstrated the facile synthesis of a known Ga(I) compound as well as the generation of new Ga(I) complexes, highlighting the use of the Ga(I)-crown ether complex as an effective starting material for new Ga(I) complexes. In addition to this study using 1,4,7,10,13-Pentaoxacyclopentadecane, there are many other studies that have used 1,4,7,10,13-Pentaoxacyclopentadecane(cas: 33100-27-5Related Products of 33100-27-5) was used in this study.

1,4,7,10,13-Pentaoxacyclopentadecane(cas: 33100-27-5) is a member of crown ether Ligands. Crown-ethers are macrocyclic polyethers capable of forming host-guest complexes, especially with inorganic and organic cations. Crown-ethers can incorporate protonated primary amine compounds by formation of ion-dipole bonds with the oxygen atoms of the chiral selector. Crown-ethers have been widely used for the separation of several pharmaceuticals both in aqueous and non-aqueous media. Related Products of 33100-27-5

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

You, Guirong; Chang, Zhi-Xin; Yan, Jizhong; Xia, Chengcai; Li, Fu-Rong; Li, Hong-Shuang published their research in Organic Chemistry Frontiers in 2021. The article was titled 《Rhodium-catalyzed sequential intermolecular hydroacylation and deconjugative isomerization toward diversified diketones》.Name: 2-Hydroxy-4-methoxybenzaldehyde The article contains the following contents:

A rhodium-catalyzed tandem intermol. hydroacylation of terminal alkyne-substituted secondary alcs. RCH(OH)(CH2)nCCH (R = Ph, thiophen-3-yl, Pr, etc.; n = 0, 1, 2) (I) with chelating aldehydes 2-OH-R1C6H3CHO (R1 = 3-CF3, 4-Cl, 5-NO2, etc.) and deconjugative isomerization of the resulting α,β-unsaturated ketones for the preparation of synthetically valuable 1,4-diketones 2-OH-R1C6H3C(O)CH2CH2C(O)R (II) is developed. Of note, the completely atom-economical protocol can be extended to the alkynyl alcs. (I) with appropriate carbon chain length, from which 1,5-diketone/1,6-diketone 2-OH-C6H4C(O)(CH2)nC(O)C6H5 (n = 3, 4) were obtained involving the short-range deconjugative isomerization. Given its robustness, broad substrate scope, and excellent regioselectivity, this approach provides a promising platform for the synthesis of diverse diketones (II). The experimental part of the paper was very detailed, including the reaction process of 2-Hydroxy-4-methoxybenzaldehyde(cas: 673-22-3Name: 2-Hydroxy-4-methoxybenzaldehyde)

2-Hydroxy-4-methoxybenzaldehyde(cas: 673-22-3) is employed in the synthesis of Schiff base ligand. It is applied as a reactant in the synthesis of LPA1R antagonists used in the inhibition of LPA-induced proliferation and contraction of normal human lung fibroblasts. Also used in the synthesis of tyrosine kinase 6 proteinase inhibitors.Name: 2-Hydroxy-4-methoxybenzaldehyde

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Wang, Cece; Zhou, Lu; Qiu, Jian; Yang, Kai; Song, Qiuling published an article in 2022. The article was titled 《Rh-Catalyzed diastereoselective addition of arylboronic acids to α-keto N-tert-butanesulfinyl aldimines: synthesis of α-amino ketones》, and you may find the article in Organic Chemistry Frontiers.Product Details of 10365-98-7 The information in the text is summarized as follows:

A diastereoselective addition of arylboronic acids to α-keto N-tert-butanesulfinyl aldimines catalyzed by a Rh(I) catalyst was reported. This reaction provided a practical method to obtain valuable chiral α-amino ketones with excellent diastereoselectivity, featuring operational simplicity, mild reaction conditions and a broad substrate scope. In the experiment, the researchers used many compounds, for example, 3-Methoxyphenylboronic acid(cas: 10365-98-7Product Details of 10365-98-7)

3-Methoxyphenylboronic acid(cas: 10365-98-7) belongs to boronic acids. Boronic acids are mild Lewis acids which are generally stable and easy to handle, making them important to organic synthesis.Product Details of 10365-98-7

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

In 2022,Wang, Tian-Ci; Wang, Pu-Sheng; Chen, Dian-Feng; Gong, Liu-Zhu published an article in Science China: Chemistry. The title of the article was 《Access to chiral homoallylic vicinal diols from carbonyl allylation of aldehydes with allyl ethers via palladium-catalyzed allylic C-H borylation》.Synthetic Route of C9H10O2 The author mentioned the following in the article:

An asym. carbonyl allylation of aldehydes with allyl ethers proceeding via allylic C-H borylation enabled by palladium and chiral phosphoric acid sequential catalysis, providing facile access to homoallylic vicinal anti-diols such as I [R1 = n-heptyl, 4-O2NC6H4, BnOCH2, etc.; R2 = H, Me, cyclohexyl, etc.; R3 = Bn, PMB, TBSO(CH2)3, etc.] in high yields and with excellent stereoselectivity was described. This protocol enabled total synthesis of aigialomycin D to be finished within 7 steps. The results came from multiple reactions, including the reaction of 2-(Benzyloxy)acetaldehyde(cas: 60656-87-3Synthetic Route of C9H10O2)

2-(Benzyloxy)acetaldehyde(cas: 60656-87-3) is a non-natural aldehyde. It undergoes enantioselective Mukaiyama aldol reaction with silylketene acetal nucleophiles in the presence of C2-symmetric bis(oxazolinyl)pyridine Cu(II) complex (catalyst).Synthetic Route of C9H10O2

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem