Month: January 2023

Phase transfer-catalyzed reactions of benzylidenebenzylamine with cinnamic acid derivatives. Synthesis of β-aryl-γ-phenyl-γ-aminobutyric acids and their derivatives was written by Potapov, V. M.;Gracheva, R. A.;Sivova, N. A.. And the article was included in Zhurnal Organicheskoi Khimii in 1989.Related Products of 6972-61-8 This article mentions the following:

Knoevenagel reaction of RCHO [R = 4-BrC₆H₄, 4-ClC₆H₄, 4-tolyl, 2- and 4-MeOC₆H₄, 4-O₂NC₆H₄, 2,4- and 3,4-(MeO)₂C₆H₃] with CH₂(CO₂H)₂ in pyridine containing piperidine gave 46-90% RCH:CHCO₂H (same R), which were esterified in EtOH containing H₂SO₄ to give 59-75% RCH:CHCO₂Et (same R) (I). PhCH:CHCOEt reacted with SOCl₂ in C₆H₆ containing pyridine and then with R¹OH [R¹ = (-)-menthyl, Bu, Me₂CH, cyclohexyl] in pyridine to give 60-92% PhCH:CHCO₂R¹ (II; same R¹). PhCH:NCH₂Ph added to I and II in MeCN containing 50% aqueous NaOH and PhCH₂NEt₃⁺ Cl^– to give 8 corresponding HO₂CCH₂CHRCHPhNH₂.HCl (III.HCl) in 37-93% yield after refluxing with 4N HCl in C₆H₆. Passing III.HCl [R = Ph, 4-O₂NC₆H₄, 4-tolyl, 4-MeO₆H₄, 3,4-(MeO)₂C₆H₃] through a Dowex-50 × 4 column gave 70-85% free III (same R). Refluxing III.HCl [R = H, 3,4-(MeO)₂C₆H₃, 4-BrC₆H₄, 4-ClC₆H₄] in C₆H₆ containing aqueous NaHCO₃ gave 68-72% lactams IV (same R), which returned III.HCl quant. after refluxing with concentrated HCl. In the experiment, the researchers used many compounds, for example, 3-(2,4-Dimethoxyphenyl)acrylic acid (cas: 6972-61-8Related Products of 6972-61-8).

3-(2,4-Dimethoxyphenyl)acrylic acid (cas: 6972-61-8) 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. But on the other hand, ethers undergo cleavage by reaction with acids. Ethers can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds. The ability to form hydrogen bonds with other compounds makes ethers particularly good solvents for a wide variety of organic compounds and a surprisingly large number of inorganic compounds.Related Products of 6972-61-8

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

Identification of an Opioid κ Receptor Subtype-Selective N-Substituent for (+)-(3R,4R)-Dimethyl-4-(3-hydroxyphenyl)piperidine was written by Thomas, James B.;Fall, Michael J.;Cooper, Julie B.;Rothman, Richard B.;Mascarella, S. Wayne;Xu, Heng;Partilla, John S.;Dersch, Christina M.;McCullough, Karen B.;Cantrell, Buddy E.;Zimmerman, Dennis M.;Carroll, F. Ivy. And the article was included in Journal of Medicinal Chemistry in 1998.Application In Synthesis of 3-(2,4-Dimethoxyphenyl)acrylic acid This article mentions the following:

A three-component library of compounds was prepared in parallel using multiple simultaneous solution-phase synthetic methodol. The compounds were biased toward opioid receptor antagonist activity by incorporating (+)-(3R,4R)-dimethyl-4-(3-hydroxyphenyl)piperidine (a potent, nonselective opioid pure antagonist) as one of the monomers. The other two monomers were N-substituted or unsubstituted Boc-protected amino acids and a range of substituted aryl carboxylic acids and were selected to add chem. diversity. Screening of these compounds in competitive binding experiments with the κ opioid receptor selective ligand [³H]U69,593 led to the discovery of a novel κ opioid receptor selective ligand, RTI-5989-29 (I). Addnl. structure-activity relationship studies suggested that I possesses lipophilic and hydrogen-bonding sites that are important to its opioid receptor potency and selectivity. These sites appear to exist predominantly within the κ receptor since the selectivity arises from a 530-fold loss of affinity of I for the μ receptor and an 18-fold increase in affinity for the κ receptor relative to the μ-selective ligand, (+)-N-[trans-4-phenyl-2-butenyl]-(3R,4R)-dimethyl-4-(3-hydroxyphenyl)piperidine. The degree of selectivity observed in the radioligand binding experiments was not observed in the functional assay. According to its ability to inhibit agonist stimulated binding of [³⁵S]GTPγS at all three opioid receptors, I behaves as a μ/κ opioid receptor pure antagonist with negligible affinity for the δ receptor. In the experiment, the researchers used many compounds, for example, 3-(2,4-Dimethoxyphenyl)acrylic acid (cas: 6972-61-8Application In Synthesis of 3-(2,4-Dimethoxyphenyl)acrylic acid).

3-(2,4-Dimethoxyphenyl)acrylic acid (cas: 6972-61-8) 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. 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.Application In Synthesis of 3-(2,4-Dimethoxyphenyl)acrylic acid

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

Polynuclear and mixed-ligand mononuclear Cu^I complexes with N-thiophosphorylated thioureas and 1,10-phenanthroline or PPh₃ was written by Safin, Damir A.;Babashkina, Maria G.;Bolte, Michael;Pape, Tania;Hahn, F. Ekkehardt;Verizhnikov, Maxim L.;Bashirov, Airat R.;Klein, Axel. And the article was included in Dalton Transactions in 2010.Reference of 66943-05-3 This article mentions the following:

Deprotonation of the N-thiophosphorylated thioureas RC(S)NHP(S)(OiPr)₂ (R = Me₂N, HL^I; iPrNH, HL^II; 2,6-Me₂C₆H₃NH, HL^III, 2,4,6-Me₃C₆H₂NH, HL^IV, aza-15-crown-5, HL^V) and reaction with CuI or Cu(NO₃)₂ in aqueous EtOH leads to the polynuclear complexes [Cu₄(L^I-S,S’)₄], [Cu₈(L^II-S,S’)₈], and [Cu₃(L^III-V-S,S’)₃]. The structures of these compounds were studied by IR, ¹H, ³¹P{¹H} NMR, UV-visible spectroscopy and elemental analyses. The crystal structures of [Cu₄L₄^I], [Cu₈L₈^II], [Cu₃L^III,IV₃] were determined by single-crystal x-ray diffraction. Reaction of the deprotonated ligands (L^I-V)^– with a mixture of CuI and 1,10-phenanthroline (phen) or PPh₃ leads to the mixed-ligand mononuclear complexes [Cu(phen)L^I-V], [Cu(PPh₃)L^I-V] or [Cu(PPh₃)₂L^I-V]. The same mixed-ligand complexes were obtained from the reaction of [Cu₄L₄^I], [Cu₈L₈^II], [Cu₃L^III-V₃] with phen or PPh₃. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Reference of 66943-05-3).

1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3) 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. But on the other hand, ethers undergo cleavage by reaction with acids. 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.Reference of 66943-05-3

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

How Metal Ion Lewis Acidity and Steric Properties Influence the Barrier to Dioxygen Binding, Peroxo O-O Bond Cleavage, and Reactivity was written by Yan Poon, Penny Chaau;Dedushko, Maksym A.;Sun, Xianru;Yang, Guang;Toledo, Santiago;Hayes, Ellen C.;Johansen, Audra;Piquette, Marc C.;Rees, Julian A.;Stoll, Stefan;Rybak-Akimova, Elena;Kovacs, Julie A.. And the article was included in Journal of the American Chemical Society in 2019.Recommanded Product: (6-Methoxypyridin-2-yl)methanol This article mentions the following:

Herein we quant. investigate how metal ion Lewis acidity and steric properties influence the kinetics and thermodn. of dioxygen binding vs. release from structurally analogous Mn-O₂ complexes, as well as the barrier to Mn peroxo O-O bond cleavage, and the reactivity of Mn oxo intermediates. Previously we demonstrated that the steric and electronic properties of MnIII-OOR complexes containing N-heterocyclic (N^Ar) ligand scaffolds can have a dramatic influence on alkylperoxo O-O bond lengths and the barrier to alkylperoxo O-O bond cleavage. Herein, we examine the dioxygen reactivity of a new Mn^II complex containing a more electron-rich, less sterically demanding N^Ar ligand scaffold, and compare it with previously reported Mn^II complexes. Dioxygen binding is shown to be reversible with complexes containing the more electron-rich metal ions. The kinetic barrier to O₂ binding and peroxo O-O bond cleavage is shown to correlate with redox potentials, as well as the steric properties of the supporting N^Ar ligands. The reaction landscape for the dioxygen chem. of the more electron-rich complexes is shown to be relatively flat. A total of four intermediates, including a superoxo and peroxo species, are observed with the most electron-rich complex. Two new intermediates are shown to form following the peroxo, which are capable of cleaving strong X-H bonds. In the absence of a sacrificial H atom donor, solvent, or ligand, serves as a source of H atoms. With TEMPOH as sacrificial H atom donor, a deuterium isotope effect is observed (k_H/k_D = 3.5), implicating a hydrogen atom transfer (HAT) mechanism. With 1,4-cyclohexadiene, 0.5 equiv of benzene is produced prior to the formation of an EPR detected MnIIIMnIV bimetallic species, and 0.5 equiv after its formation. In the experiment, the researchers used many compounds, for example, (6-Methoxypyridin-2-yl)methanol (cas: 63071-12-5Recommanded Product: (6-Methoxypyridin-2-yl)methanol).

(6-Methoxypyridin-2-yl)methanol (cas: 63071-12-5) 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. 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).Recommanded Product: (6-Methoxypyridin-2-yl)methanol

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

The electro-oxidation of primary alcohols via a coral-shaped cobalt metal-organic framework modified graphite electrode in neutral media was written by Khakyzadeh, Vahid;Sediqi, Salbin. And the article was included in Scientific Reports in 2022.Formula: C8H10O2 This article mentions the following:

The electro-oxidation of alcs. into corresponding aldehydes achieved enormous attention. However, numerous challenges remain in exploring catalytic systems with high conversion efficiency and selectivity. Considering the worldwide attention toward metal-organic frameworks (MOFs) as outstanding crystalline porous materials, many chemists have been encouraged to use them in organic transformations. In this study, a novel coral-shaped cobalt organic framework was grown onto the surface of a functionalized graphite electrode (Co-MOF/C) to fabricate an efficient modified electrode in the electro-oxidation alcs. The modified Co-MOF/C electrode showed high stability, large surface area, rich pores, and good conductivity as a desirable water-stable working electrode for selective oxidation of alcs. into aldehydes in good to excellent yields under a diffusion-controlled process. In the experiment, the researchers used many compounds, for example, (4-Methoxyphenyl)methanol (cas: 105-13-5Formula: C8H10O2).

(4-Methoxyphenyl)methanol (cas: 105-13-5) 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. But ether is more polar than alkenes. 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.Formula: C8H10O2

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

Application of Vinyl Nucleophiles in Matteson Homologations was written by Kinsinger, Thorsten;Kazmaier, Uli. And the article was included in Organic Letters in 2022.Category: ethers-buliding-blocks This article mentions the following:

The Matteson homologation with vinyl nucleophiles was found to be a versatile tool for the synthesis of highly substituted and functionalized allyl boronic esters I (R = phenylethyl, Me, butan-2-yl, etc.), II (R¹ = H, Me; R² = H, Me; R³ = H, Me), III and IV (R⁴ = Me, Et, n-Pr; R⁵ = H, Me). High yields and stereoselectivities are obtained with sterically demanding alkyl boronic esters and/or Grignard reagents. With the application of such vinyl Matteson homologations, the polyketide fragment of lagunamide B is synthesized. In the experiment, the researchers used many compounds, for example, (4-Methoxyphenyl)methanol (cas: 105-13-5Category: ethers-buliding-blocks).

(4-Methoxyphenyl)methanol (cas: 105-13-5) 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. 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).Category: ethers-buliding-blocks

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

Cationic Pd(II)-Catalyzed Fujiwara-Moritani Reactions at Room Temperature in Water was written by Nishikata, Takashi;Lipshutz, Bruce H.. And the article was included in Organic Letters in 2010.SDS of cas: 56619-93-3 This article mentions the following:

Pd^II-catalyzed Fujiwara-Moritani reactions can be carried out without external acid at room temperature and in water as the only medium. A highly active cationic Pd^II catalyst, [Pd(MeCN)₄](BF₄)₂, easily activates aromatic C-H bonds to produce electron-rich cinnamates in good yields. In the experiment, the researchers used many compounds, for example, N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3SDS of cas: 56619-93-3).

N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3) 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. But on the other hand, ethers undergo cleavage by reaction with acids. 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.SDS of cas: 56619-93-3

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

A regioselective synthesis of 1-haloisoquinolines via ruthenium-catalyzed cyclization of O-methylbenzohydroximoyl halides with alkynes was written by Chinnagolla, Ravi Kiran;Pimparkar, Sandeep;Jeganmohan, Masilamani. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2013.HPLC of Formula: 16356-02-8 This article mentions the following:

A ruthenium-catalyzed highly regioselective cyclization of substituted N-methoxy benzimidoyl halides with alkynes in the presence of CsOAc (25 mol%) to give substituted 1-halo and 1-alkoxy substituted isoquinolines in good to excellent yields is described. E.g., in presence of [(RuCl₂(p-cymene))₂] and CsOAc, reaction of 4-MeC₆H₄CCl:NOMe and PhCCMe gave 77% isoquinoline derivative (I). 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. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. Ethyl ether is an excellent solvent for extractions and for a wide variety of chemical reactions. It is also used as a volatile starting fluid for diesel engines and gasoline engines in cold weather. Dimethyl ether is used as a spray propellant and refrigerant. Methyl t-butyl ether (MTBE) is a gasoline additive that boosts the octane number and reduces the amount of nitrogen-oxide pollutants in the exhaust. The ethers of ethylene glycol are used as solvents and plasticizers.HPLC of Formula: 16356-02-8

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

Probing Electrolyte Influence on CO₂ Reduction in Aprotic Solvents was written by Gomes, Reginaldo J.;Birch, Chris;Cencer, Morgan M.;Li, Chenyang;Son, Seoung-Bum;Bloom, Ira D.;Assary, Rajeev S.;Amanchukwu, Chibueze V.. And the article was included in Journal of Physical Chemistry C in 2022.Application of 112-49-2 This article mentions the following:

Selective CO₂ capture and electrochem. conversion are important tools in the fight against climate change. Industrially, CO₂ is captured using a variety of aprotic solvents due to their high CO₂ solubility However, most research efforts on electrochem. CO₂ conversion use aqueous media and are plagued by competing hydrogen evolution reaction (HER) from water breakdown. Fortunately, aprotic solvents can circumvent HER, making it important to develop strategies that enable integrated CO₂ capture and conversion. However, the influence of ion solvation and solvent selection within nonaqueous electrolytes for efficient and selective CO₂ reduction is unclear. In this work, we show that the bulk solvation behavior within the nonaqueous electrolyte can control the CO₂ reduction reaction and product distribution occurring at the catalyst-electrolyte interface. We study different tetrabutylammonium (TBA) salts in two electrolyte systems with glyme ethers (e.g., 1,2 dimethoxyethane or DME) and DMSO (DMSO) as a low and high dielec. constant medium, resp. Using spectroscopic tools, we quantify the fraction of ion pairs that forms within the electrolyte. Also, we show how ion pair formation is prevalent in DME and is dependent on the anion type. More importantly, we show that as ion pair formation decreases within the electrolyte, CO₂ current densities increase, and a higher CO Faradaic efficiency is observed at low overpotentials. Meanwhile, in an electrolyte medium where the ion pair fraction does not change with the anion type (such as in DMSO), a smaller influence of solvation is observed on CO₂ current densities and product distribution. By directly coupling bulk solvation to interfacial reactions and product distribution, we showcase the importance and utility of controlling the reaction microenvironment in tuning the electrocatalytic reaction pathways. Insights gained from this work will enable novel electrolyte designs for efficient and selective CO₂ conversion to desired fuels and chems. In the experiment, the researchers used many compounds, for example, 2,5,8,11-Tetraoxadodecane (cas: 112-49-2Application of 112-49-2).

2,5,8,11-Tetraoxadodecane (cas: 112-49-2) 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).Application of 112-49-2

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

Rhodium-catalyzed intramolecular alkynylsilylation of alkynes was written by Shintani, Ryo;Kurata, Hiroki;Nozaki, Kyoko. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2015.Application of 16356-02-8 This article mentions the following:

Rhodium-catalyzed intramol. alkynylsilylation of alkynes is described. The reaction proceeds through syn-insertion by a cationic rhodium/triarylphosphine catalyst, representing the first alkynylsilylation of alkynes via the cleavage of a C(sp)-Si bond by transition-metal catalysis. A highly enantioselective variant is also described for the creation of a silicon stereogenic center. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Application 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. 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.Application of 16356-02-8

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