Category: 16356-02-8

Cobalt-catalyzed cyclization of N-methoxy benzamides with alkynes using an internal oxidant through C-H/N-O bond activation was written by Sivakumar, Ganesan;Vijeta, Arjun;Jeganmohan, Masilamani. And the article was included in Chemistry – A European Journal in 2016.Reference of 16356-02-8 This article mentions the following:

The cyclization of substituted N-methoxy benzamides with alkynes in the presence of an easily affordable cobalt complex and NaOAc provided isoquinolone derivatives, e.g., I in good to excellent yields. The cyclization reaction was compatible with a range of functional group-substituted benzamides, as well as ester- and alc.-substituted alkynes. The cobalt complex [Co^IIICp*(OR)₂] (R = Me or Ac) served as an efficient catalyst for the cyclization reaction. Later, isoquinolone derivatives were converted into 1-chloro and 1-bromo substituted isoquinoline derivatives in excellent yields in the presence of POCl₃ or PBr₃. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Reference of 16356-02-8).

1,4-Dimethoxy-2-butyne (cas: 16356-02-8) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Reference of 16356-02-8

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

Directed Evolution of a Cp*Rh^III-Linked Biohybrid Catalyst Based on a Screening Platform with Affinity Purification was written by Kato, Shunsuke;Onoda, Akira;Taniguchi, Naomasa;Schwaneberg, Ulrich;Hayashi, Takashi. And the article was included in ChemBioChem in 2021.Safety of 1,4-Dimethoxy-2-butyne This article mentions the following:

Directed evolution of Cp*Rh^III-linked nitrobindin (NB), a biohybrid catalyst, was performed based on an in vitro screening approach. A key aspect of this effort was the establishment of a high-throughput screening (HTS) platform that involves an affinity purification step employing a starch-agarose resin for a maltose binding protein (MBP) tag. The HTS platform enables efficient preparation of the purified MBP-tagged biohybrid catalysts in a 96-well format and eliminates background influence of the host E. coli cells. Three rounds of directed evolution and screening of more than 4000 clones yielded a Cp*Rh^III-linked NB(T98H/L100K/K127E) variant with a 4.9-fold enhanced activity for the cycloaddition of acetophenone oximes with alkynes. It is confirmed that this HTS platform for directed evolution provides an efficient strategy for generating highly active biohybrid catalysts incorporating a synthetic metal cofactor. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Safety of 1,4-Dimethoxy-2-butyne).

1,4-Dimethoxy-2-butyne (cas: 16356-02-8) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).Safety of 1,4-Dimethoxy-2-butyne

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

Nickel-Catalyzed Reaction of Thioisatins and Alkynes: A Facile Synthesis of Thiochromones was written by Inami, Tasuku;Kurahashi, Takuya;Matsubara, Seijiro. And the article was included in Organic Letters in 2014.Safety of 1,4-Dimethoxy-2-butyne This article mentions the following:

A new synthetic method for thiochromones was developed by using nickel-catalyzed decarbonylative cycloaddition of readily available thioisatins with alkynes. This reaction proceeded under very mild conditions and has quite high functional group compatibility. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Safety of 1,4-Dimethoxy-2-butyne).

1,4-Dimethoxy-2-butyne (cas: 16356-02-8) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Safety of 1,4-Dimethoxy-2-butyne

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

Gold(I)-catalyzed addition of carboxylic acids to internal alkynes in aqueous medium was written by Gonzalez-Liste, Pedro J.;Garcia-Garrido, Sergio E.;Cadierno, Victorio. And the article was included in Organic & Biomolecular Chemistry in 2017.HPLC of Formula: 16356-02-8 This article mentions the following:

The efficient hydro-oxycarbonylation of sym. and unsym. internal alkynes RCCR¹ (R = R¹ = CH₂CH₃; R = C₆H₅, R¹ = CH₃; R = CH₃, R¹ = C(O)₂CH₂CH₃, etc.) with carboxylic acids R²C(O)₂H [R² = C₆H₅, (CH₂)₅CH₃, cyclohexyl, etc.] in water at 60 °C, employs the catalytic system [AuCl(PPh₃)]/AgOAc (5 mol%) has been reported. This simple and eco-friendly protocol allows for the synthesis of a wide variety of trisubstituted enol esters (Z)-I and (Z)-II in high yields and with complete Z-stereoselectivity. The use of microwave irradiation as an alternative energy source has also been evaluated. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8HPLC of Formula: 16356-02-8).

1,4-Dimethoxy-2-butyne (cas: 16356-02-8) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive. At room temperature, ethers are pleasant-smelling colourless liquids. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil.HPLC of Formula: 16356-02-8

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

Copper-catalyzed ortho-alkenylation of quinoline N-oxides with alkynes was written by Jiang, Linjuan;Hu, Hui;Liu, Yuanhong. And the article was included in Organic Chemistry Frontiers in 2022.Related Products of 16356-02-8 This article mentions the following:

A copper-catalyzed regioselective C-2 alkenylation of quinoline N-oxides with alkynes and pinacol diborane was developed. This method provided efficient access to a wide variety of deoxygenated 2-alkenyl quinolines with good functional group tolerance. In particular, highly regio- and stereoselective reactions were observed with unsym. alkynes such as aryl(alkyl)acetylenes and enynes. The reaction involved borylcupration of alkynes, captured of the catalytically generated alkenyl copper species by quinoline N-oxides and deborylation. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Related Products of 16356-02-8).

1,4-Dimethoxy-2-butyne (cas: 16356-02-8) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil. At room temperature, ethers are pleasant-smelling colourless liquids. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil.Related Products of 16356-02-8

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

Aromatic Homologation by Non-Chelate-Assisted Rh^III-Catalyzed C-H Functionalization of Arenes with Alkynes was written by Pham, Manh V.;Cramer, Nicolai. And the article was included in Angewandte Chemie, International Edition in 2014.Electric Literature of C6H10O2 This article mentions the following:

Larger condensed arenes are of interest owing to their electro- and photochem. properties. An efficient synthesis is the catalyzed aromatic annulation of a smaller arene with two alkyne mols. Besides difunctionalized starting materials, directed C-H functionalization can be used for such aromatic homologation. However, thus far the requirement of either pre-functionalized substrates or suitable directing groups were limiting this approach. Herein, we describe a rhodium(III)-catalyzed method allowing the use of completely unbiased arenes and internal alkynes. The reaction works best with copper(II) 2-ethylhexanoate and decabromodiphenyl ether as the oxidant combination. E.g., in presence of [(Cp^*RhCl₂)₂], copper(II) 2-ethylhexanoate, and decabromodiphenyl ether, homologation of naphthalene with BuCCBu gave 60% anthracene derivative (I). This aromatic annulation tolerates a variety of functional groups and delivers homologated condensed arenes. Aside from simple benzenes, naphthalenes, and higher condensed arenes provide access to highly substituted and highly soluble acene structures having important electronic and photophys. properties. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Electric Literature of C6H10O2).

1,4-Dimethoxy-2-butyne (cas: 16356-02-8) belongs to ethers. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly autoxidize to form hydroperoxides and dialkyl peroxides. If concentrated or heated, these peroxides may explode. To prevent such explosions, ethers should be obtained in small quantities, kept in tightly sealed containers, and used promptly.Electric Literature of C6H10O2

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