Tag: M.W=100-150

Pegolotti, J. A. published the artcileAllylic rearrangements. L. Reactions of α- and γ-trifluoromethylallyl alcohols with thionyl chloride and thermal decomposition of the chlorosulfinate intermediates, Synthetic Route of 83706-94-9, the publication is Journal of the American Chemical Society (1961), 3251-8, database is CAplus.

The reactions of α-(trifluoromethyl)allyl alc. (I) and γ-(trifluoromethyl)allyl alc. (II) with SOCl₂ in Et₂O and SOCl₂ were investigated. In the absence of amines, I in either solvent yielded α-(trifluoromethyl)allyl chlorosulfinate (III) only. With I, Bu₃N, and SOCl₂ (equimolar in ether) the products were 68% III and 32% γ-(trifluoromethyl)allyl chloride (IV) after 1 hr. The presence of Bu₃NHCl in the mixture gave small amounts of IV. II and SOCl₂ in ether yielded γ-(trifluoromethyl)allyl chlorosulfinate (V), which slowly gave IV on standing. In the presence of Bu₃N, II and SOCl₂ gave IV exclusively. III and V, the first isolable allylic chlorosulfinates outside of allyl chlorosulfinate itself, were thermally decomposed with no solvent and in n-decane and nitrobenzene and the rates of decomposition measured by the rate of evolution of SO₂ [compound, solvent, decompn, temperature, and rate (10⁵k. sec.^-1, extrapolated to 100°) given]: III, none (3 runs), 108-110° (103°, 105-106°), 6.5 (6.2, 7.3); III, nitrobenzene, 106-108°, 10.0; III, n-decane, 124°, 1.5; V, none (2 runs), 105° (139-142°), 126 (0.27); V, nitrobenzene (2 runs), 115-116° (118-120°), 5.1 (8.8). The insensitivity of the decomposition to solvent was explained in terms of a concerted reaction with predominant covalent character maintained in the intermediate through the rearrangement sequence. II was prepared by the procedure of McBee (CA 49, 10171b). I was prepared by addition of CF₃CHO to the Grignard reagent from vinyl bromide and Mg in tetrahydrofuran; I formed an azeotrope, b. 102-3°, with the solvent. Chromatography of the azeotrope gave I, b. 91.5°, n²⁵_D 1.3450. The α-napthylurethan of I m. 121-3°. Adding 8.9 g. SOCl₂ to 9.4 g. II and 13.9 g. Bu₃N over 30 min. at 0°, stirring 1 hr., then flash distilling gave IV, b. 82.5-83°, n²⁵_D 1.3610. γ-(Trifluoromethyl)allyl n-amyl sulfite (VI) was prepared by adding dropwise over 30 min. a mixture of 3.0 g. II and 1.9 g. anhydrous pyridine to a cooled (-20 to -30°) solution of 5.12 g. n-amyl chlorosulfinate in ether. H₂O was added after 45 min., the layers separated, the ether layer washed, dried, and distilled to yield 2.05 g. VI, b₄ 100-102°, n²⁵_D 1.4099. α-(Trifluoromethyl)allyl n-amyl sulfite (VII) was prepared similarly, b₅ 80-2°, n²⁵_D 1.4030. Addition of 4.86 g. SOCl₂ in ether to a stirred solution of 3.57 g. II in 60 ml. ether at 0° and distillation gave 1.23 g. V, b₆ 55°, n²⁵_D 1.4089. Reaction of V with n-amyl alc. gave VI. Addition of 3.1 g. I to 14.3 g. SOCl₂ and 5.3 g. Bu₃N over 45 min. at 0°, with stirring continued 1 hr., and distillation gave 2.78 g. III, b₃₉ 52°, n²⁵_D 1.4088. Reaction of III with n-amyl alc. gave VII. The refractive indexes of III and V did not change during 5 min. in the refractometer.

Journal of the American Chemical Society published new progress about 83706-94-9. 83706-94-9 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is (E)-4,4,4-Trifluorobut-2-en-1-ol, and the molecular formula is C4H5F3O, Synthetic Route of 83706-94-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Xu, Wanling published the artcileElectrochemical hydrogenation of biomass-based furfural in aqueous media by Cu catalyst supported on N-doped hierarchically porous carbon, Synthetic Route of 111-29-5, the publication is Applied Catalysis, B: Environmental (2022), 121062, database is CAplus.

Electrochem. hydrogenation (ECH) is a particularly important and environmentally friendly approach to obtain biomass-based fuels and high value-added fine chems. without using external hydrogen. Herein, we reported a highly efficient and selective ECH of furfural (FF) into furfuryl alc. (FA) with Cu-based electrocatalyst in aqueous alk. media. Under the optimal conditions, FA selectivity close to 100% with 99% FF conversion and total Faradaic efficiency above 95% were obtained with the electrocatalyst. Mechanism investigation suggests an ECH mechanism for FA formation, which is highly potential-dependent to FA selectivity, requiring low and well-matched concentrations between active hydrogen (H_ads) species and FA radical on the Cu surface. Moreover, the electrocatalyst shows an excellent stability and recyclability during the eight-time consecutive recycling experiments, yielding a total amount of 1011 mg FA. This work thus highlights an important guidance for electrocatalytic upgrading of biomass-based platform mols. in an environmentally friendly way.

Applied Catalysis, B: Environmental published new progress about 111-29-5. 111-29-5 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic hydrocarbon chain,Alcohol,Ploymers, name is Pentane-1,5-diol, and the molecular formula is C20H23N3O2S, Synthetic Route of 111-29-5.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Liu, Jingping published the artcileFree-Radical-Promoted Dehydrogenative Coupling of Polyfluorinated Alcohol with Quinone, Chromone, and Coumarin, Name: 3,3,3-Trifluoropropan-1-ol, the publication is Organic Letters (2020), 22(12), 4844-4847, database is CAplus and MEDLINE.

A free-radical-mediated dehydrogenative cross-coupling reaction of polyfluorinated alc. with quinone, coumarin, and chromone was developed. It provides a sustainable and practical strategy for installation of fluorine atom into organic mols. by using polyfluorinated alcs.

Organic Letters published new progress about 2240-88-2. 2240-88-2 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Aliphatic hydrocarbon chain,Alcohol, name is 3,3,3-Trifluoropropan-1-ol, and the molecular formula is C3H5F3O, Name: 3,3,3-Trifluoropropan-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Wang, Bing-Lin published the artcileSynthesis of trifluoromethylated analogues of α-L-fucofuranose and α-L-4,6-dideoxyxylohexopyranose, Formula: C4H5F3O, the publication is Journal of Fluorine Chemistry (2006), 127(4-5), 580-587, database is CAplus.

Efficient strategy to trifluoromethylated trans-disubstituted alkene I was developed starting from com. available 4,4,4-trifluoro-3-oxo-butyric acid Et ester. 6-Deoxy-6,6,6-trifluorosugars II and III were synthesized from I in high stereoselectivity and in a straightforward fashion. The key steps were Sharpless asym. dihydroxylation, regioselective ring opening of trifluoromethylated cyclic sulfate, Horner-Wadsworth-Emmons reaction, oxidation and intramol. heterocyclization. It was noteworthy that the oxidation of alcs. followed by deprotection and acetylation gave the single isomer target mols. II and III, resp.

Journal of Fluorine Chemistry published new progress about 83706-94-9. 83706-94-9 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is (E)-4,4,4-Trifluorobut-2-en-1-ol, and the molecular formula is C7H10N2O2, Formula: C4H5F3O.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Shi, Yao published the artcileComputational Chemistry-Assisted Highly Selective Radical Cascade Cyclization of 1,6-Enynes with Thiols: Access to Sulfur-Substituted 4-Enyl-2-Pyrrolidones, Quality Control of 4410-99-5, the publication is Journal of Organic Chemistry (2022), 87(15), 9479-9487, database is CAplus and MEDLINE.

In this study, an efficient method for the synthesis of sulfur-substituted 4-enyl-2-pyrrolidones I (R¹ = H, 2-Me, 2-Br, 3-Cl, etc.; R² = H, 4-Me; R³ = 4-methylphenyl, (2-chlorophenyl)methyl, furan-2-ylmethyl, etc.) was successfully developed through AIBN-promoted highly selective 5-exo-dig radical cascade cyclization of 1,6-enynes II with sulfur R³SH sources with the aid of theor. and computational chem. This protocol enables the first practical and green synthesis of an array of 4-enyl-2-pyrrolidones I in moderate-to-good yields with broad substrate scopes and high regioselectivities (>20:1). Moreover, excellent stereoselectivities have also been achieved (up to >20:1, Z/E). Most interestingly, when the sulfur source is electron-rich thiophenol, reverse stereoselectivities were discovered. In addition, the control experiments indicate that the cascade cyclization is realized by radical reactions, and the detailed reaction mechanism and regioselectivities have also been explained by theor. studies.

Journal of Organic Chemistry published new progress about 4410-99-5. 4410-99-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Benzene, name is 2-Phenylethanethiol, and the molecular formula is C17H14F3N3O2S, Quality Control of 4410-99-5.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Gao, Pan published the artcileCopper-Catalyzed Asymmetric Defluoroborylation of 1-(Trifluoromethyl)Alkenes, Application In Synthesis of 83706-94-9, the publication is Chem (2018), 4(9), 2201-2211, database is CAplus.

Gem-Difluoroalkenes have steric and electronic profiles similar to those of ketones, aldehydes, and esters, and consequently have been used widely as carbonyl isosteres in modern drug discovery. Although many attempts have been made to achieve gem-difluoroalkenes, the induction of enantioselectivity at the α position of a gem-difluorovinyl group still remains a challenge. Herein, an efficient method for the construction of gem-difluoroallylboronates with high enantiomeric excess via a copper-catalyzed defluoroborylation of 1-(trifluoromethyl)alkenes with B₂pin₂ is described. The reaction conditions were mild, and a variety of common functional groups, such as ether, fluoride, chloride, bromide, iodide, ester, cyano, sulfide, amino, and indoyl groups, were well tolerated. Furthermore, we not only applied this developed system as a powerful synthetic tool for the late-stage modification of complex compounds but also highlighted the utility of the formed compounds in synthesis.

Chem published new progress about 83706-94-9. 83706-94-9 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is (E)-4,4,4-Trifluorobut-2-en-1-ol, and the molecular formula is C4H5F3O, Application In Synthesis of 83706-94-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Mao, Jialin published the artcileSynthesis and antituberculosis activity of novel mefloquine-isoxazole carboxylic esters as prodrugs, Formula: C3H5F3O, the publication is Bioorganic & Medicinal Chemistry Letters (2010), 20(3), 1263-1268, database is CAplus and MEDLINE.

Previously, isoxazole I [R = EtO (II)] was reported to have excellent antituberculosis activity against both replicating and non-replicating Mycobacterium tuberculosis, with a min. inhibitory concentration (MIC) of 0.9 μM and 12.2 μM, resp. In this study, the antituberculosis activity of II was further investigated. Its activity appeared to be very specific for organisms of the M. tuberculosis complex and it effected significant reductions of bacterial numbers in infected macrophages with an EC₉₀ of 4.1 μM. More importantly, the increased in vitro antituberculosis activity of the corresponding acid I (R = HO) at pH 6.0 suggested that it may be active in vivo in an acidic environment produced as a consequence of inflammation in the lungs of TB patients. The fact that various ester bioisosteres of compound II lost anti-TB activity further suggested that II may function as a prodrug. The detailed structure-activity relationships (SARs) from this study should facilitate our ultimate goal of improving the anti-TB potency of this isoxazole ester series.

Bioorganic & Medicinal Chemistry Letters published new progress about 2240-88-2. 2240-88-2 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Aliphatic hydrocarbon chain,Alcohol, name is 3,3,3-Trifluoropropan-1-ol, and the molecular formula is C3H5F3O, Formula: C3H5F3O.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Li, Yingxiu published the artcileDiscovery of 4-piperazinyl-2-aminopyrimidine derivatives as dual inhibitors of JAK2 and FLT3, Application of 2-Morpholinoethanol, the publication is European Journal of Medicinal Chemistry (2019), 111590, database is CAplus and MEDLINE.

Hybridization strategy is an effective strategy to obtain multi-target inhibitors in drug design. In this study, we assembled the pharmacophores of momelotinib and tandutinib to get a series of 4-piperazinyl-2-aminopyrimidine derivatives All compounds were tested for the inhibition of JAK2 and FLT3 enzymes, of which, compounds with potent enzyme activities were assayed for antiproliferative activities against three cancer cell lines (HEL, MV4-11, and HL60). The structure-activity relationship studies were conducted through variations in two regions, the “A” Ph ring and “B” Ph ring. Compound 14j showed the most balanced in vitro inhibitory activity against JAK2 and FLT3 (JAK2 IC₅₀ = 27 nM, FLT3 IC₅₀ = 30 nM), and it also showed potent inhibition against the above tested cell lines. In the cellular context, 14j strongly induced apoptosis by arresting cell cycle in the G₁/S phase, and was selected as a promising JAK2/FLT3 dual inhibitor.

European Journal of Medicinal Chemistry published new progress about 622-40-2. 622-40-2 belongs to alcohols-buliding-blocks, auxiliary class Morpholine,Alcohol, name is 2-Morpholinoethanol, and the molecular formula is C6H13NO2, Application of 2-Morpholinoethanol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Li, Yiling published the artcileAmphiphilic polymer-encapsulated Au nanoclusters with enhanced emission and stability for highly selective detection of hypochlorous acid, Recommanded Product: 2-Phenylethanethiol, the publication is RSC Advances (2021), 11(24), 14678-14685, database is CAplus and MEDLINE.

It is of vital importance to develop probes to monitor hypochlorous acid (HClO) in biol. systems as HClO is associated with many important physiol. and pathol. processes. Metal nanoclusters (NCs) are promising luminescent nanomaterials for highly reactive oxygen species (hROS) detection on the basis of their strong reaction ability with hROS. However, metal NCs typically can respond to most common hROS and are susceptible to etching by biothiols, hindering their application in the construction of effective HClO probes. Herein, we proposed a strategy to develop a nanoprobe based on Au NCs for highly sensitive and selective detection of HClO. We synthesized luminescent benzyl mercaptan-stabilized Au NCs and encapsulated them with an amphiphilic polymer (DSPE-PEG). After encapsulation, an obvious emission enhancement and good resistance to the etching by biothiols for Au NCs were achieved. More importantly, the DSPE-PEG encapsulated Au NCs can be used as a nanoprobe for detection of HClO with good performance. The luminescence of the Au NCs was effectively and selectively quenched by HClO. A good linear relationship with the concentration of HClO in the range of 5-35 μM and a limit of detection (LOD) of 1.4 μM were obtained. Addnl., this nanoprobe was successfully used for bioimaging and monitoring of HClO changes in live cells, suggesting the application potential of the as-prepared amphiphilic polymer-encapsulated Au NCs for further HClO-related biomedical research.

RSC Advances published new progress about 4410-99-5. 4410-99-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Benzene, name is 2-Phenylethanethiol, and the molecular formula is C8H10S, Recommanded Product: 2-Phenylethanethiol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Yao, Yuhang published the artcileStrong Fluorescent Lanthanide Salen Complexes: Photophysical Properties, Excited-State Dynamics, and Bioimaging, Quality Control of 14703-69-6, the publication is Inorganic Chemistry (2019), 58(3), 1806-1814, database is CAplus and MEDLINE.

The synthesis, excited-state dynamics, and biol. application of luminescent lanthanide salen complexes (Ln = Lu, Gd, Eu, Yb, salen = N,N’-bis(salicylidene)ethylenediamine-based ligands) with sandwich structures are described. Among them, Lu(III) complexes show unusually strong ligand-centered fluorescence with quantum yields up to 62%, although the metal center is close to a chromophore ligand. The excited-state dynamic studies including ultrafast spectroscopy for Ln-salen complexes revealed that their excited states are solely dependent on the salen ligands and the ISC rates are slow (10⁸-10⁹ s^-1). Importantly, time-dependent d. functional theory calculations attribute the low energy transfer efficiency to the weak spin-orbital coupling (SOC) between the singlet and triplet excited states. More importantly, Lu-salen has been applied as a mol. platform to construct fluorescence probes with organelle specificity in living cell imaging, which demonstrates the advantages of the sandwich structures as being capable of preventing intramol. metal-ligand interactions and behaviors different from those of the previously reported Zn-salens. Most importantly, the preliminary study for in vivo imaging using a mouse model demonstrated the potential application of Ln coordination complexes in therapeutic and diagnostic bioimaging beyond living cells or in vitro.

Inorganic Chemistry published new progress about 14703-69-6. 14703-69-6 belongs to alcohols-buliding-blocks, auxiliary class Amine,Benzene,Phenol, name is 3-(Methylamino)phenol, and the molecular formula is C13H11NO, Quality Control of 14703-69-6.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts