Category: 20117-47-9

Shu, Chao published the artcilePhotoinduced Fragmentation Borylation of Cyclic Alcohols and Hemiacetals, Quality Control of 20117-47-9, the publication is Organic Letters (2020), 22(18), 7213-7218, database is CAplus and MEDLINE.

A visible-light photoinduced fragmentation borylation of O-phthalimido cycloalkanols with bis(catecholato)diboron is described. Structurally diverse keto and formyloxy alkyl boronic esters are conveniently prepared by radical-mediated ring-opening of cyclic alcs. and hemiacetals, resp. The reactions proceed under mild conditions in the absence of additives or photocatalysts, display excellent functional group tolerance, and allow cleavage of 4-, 5-, 6-, and 7-membered ring substrates. The mechanism proceeds via sequential homolytic N-O and C-C bond cleavages, the latter of which involves β-scission of an alkoxy radical, generating a carbonyl and an alkyl radical that is trapped by the diboron reagent. Spectroscopic studies suggest direct photoexcitation of either the phthalimide or diboron substrates with blue-light can initiate a radical chain mechanism.

Organic Letters published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C8H6ClNO, Quality Control of 20117-47-9.

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

Tsarev, Vasily N. published the artcileP-chiral monodentate diamidophosphites – New and efficient ligands for palladium-catalysed asymmetric allylic substitution, Recommanded Product: 1-Methylcyclobutan-1-ol, the publication is European Journal of Organic Chemistry (2004), 2214-2222, database is CAplus.

Monodentate hexahydropyrrolodiazaphosphole ligands I [R = MeO, Me₂CHO, Me₃CO, (F₃C)₂CHO, 1-Me-1-cyclobutoxy, 1-adamantyloxy, (-)-menthyloxy, PhO, Et₂N, 1-piperidinyl] are prepared and used as ligands for enantioselective allylic substitution and amination reactions of 1,3-diphenylallyl acetate with sodium 4-methylbenzenesulfinate, benzylamine, and di-Me malonate to give substitution products in up to 97% ee. Reaction of alcs. or amines with I (R = Cl) [prepared in one step from (2R)-2-(phenylaminomethyl)pyrrolidine and PCl₃] yields I [R = MeO, Me₂CHO, Me₃CO, (F₃C)₂CHO, 1-Me-1-cyclobutoxy, 1-adamantyloxy, (-)-menthyloxy, PhO, Et₂N, 1-piperidinyl]. I are isolated as mixtures of epimers at phosphorus favoring the (R^P)-configuration. Dinaphthodioxaphosphepines derived from (R)-BINOL are also prepared as nonracemic ligands for comparison. Dimeric rhodium complexes and a monomeric rhodium complexes are prepared from I and [Rh(CO)₂Cl]₂ and characterized by ³¹P NMR. (allyl)palladium complexes derived from I and allylpalladium chloride dimer are prepared as catalysts for allylic substitution and amination reactions; the complexes can also be generated in situ using either allylpalladium chloride dimer or tris(dibenzylideneacetone)dipalladium as precursors, but in some cases the use of in situ generated catalysts gives products with decreased enantioselectivities. The most effective catalysts are those containing phosphine ligands with moderate π-acidity; less π-acidic ligands give decreased enantioselectivities. The enantioselectivity of allylic amination reactions using I and their derived palladium complexes increases as the cone angle of the phosphine increases. Allylic alkylation of (allyl)(methyl)carbonate with a carborane-containing phenylacetic acid ester gives an (allyl)(carboranyl)phenylacetate ester in up to 73% ee, the first direct asym. reaction for a carborane derivative

European Journal of Organic Chemistry published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C2H2N4O2, Recommanded Product: 1-Methylcyclobutan-1-ol.

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

Holmes, J. L. published the artcileHeats of formation of ionic and neutral enols of acetaldehyde and acetone, SDS of cas: 20117-47-9, the publication is Journal of the American Chemical Society (1982), 104(9), 2648-9, database is CAplus.

CH₂:C(OH)R (I, R = H, Me) are formed, together with C₂H₄, in the pyrolysis of II (R = H, Me) at 950°/10^-3 torr in a tubular quartz reactor leading to an ionization chamber; the pyrolysis of II (R = Me) at >950° gave CH₄ and CH₂:CO at the expense of enol. The ionization energies, accurately determined by the impact of a monoenergetic electron beam and the ionization efficiency curve threshold, were 9.15 ± 0.05 and 8.48 ± 0.05 eV. The low cross-section for ionization of I is due to the small Franck-Condon factors for the adiabatic transition which are related to the difference in the preferred conformation of the OH group in I and its radical cation. The formation heat of I and its radical cations are calculated; the enol radical cations are more stable than the keto or aldehyde radical cations in contrast to the neutral species. The formation heat increment for the -OCH: fragment was also estimated

Journal of the American Chemical Society published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, SDS of cas: 20117-47-9.

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

Rakhmatullina, L. Kh. published the artcileSynthesis of 2-pentanol, Category: alcohols-buliding-blocks, the publication is Khimiko-Farmatsevticheskii Zhurnal (1989), 23(3), 321-6, database is CAplus.

A review with 8 references including the following methods of 2-pentanol synthesis: (1) hydration of methylenecyclobutane, followed by hydrogenolysis of the 1-methylcyclobutanol obtained, (2) hydrogenolysis of 2-methylfuran along with hydrogenation of the 2-pentanone (I) formed, and (3) condensation of PrCO₂H with acetone, followed by hydrogenation of the I obtained.

Khimiko-Farmatsevticheskii Zhurnal published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, Category: alcohols-buliding-blocks.

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

Nikishin, G. I. published the artcileOxidative splitting of 1-methylcycloalkanols by the lead(IV) acetate-copper(II) acetate system, Related Products of alcohols-buliding-blocks, the publication is Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1979), 1548-53, database is CAplus.

Oxidative cleavage of title alcs. I (n = 1-4) with Pb(OAc)₄-Cu(OAc)₂ gave 76-99% MeCO(CH₂)_nCH:CH₂ with 20-49% I conversion via the intermediate MeCO(CH₂)_n+2â€?radical. The reactivity of I decreased in the order of n 1 > 2 > 4 > 3.

Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, Related Products of alcohols-buliding-blocks.

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

Ruzicka, Frank published the artcileMethane monooxygenase catalyzed oxygenation of 1,1-dimethylcyclopropane. Evidence for radical and carbocationic intermediates, COA of Formula: C5H10O, the publication is Biochemistry (1990), 29(7), 1696-700, database is CAplus and MEDLINE.

Methane monooxygenase of Methylosinus trichosporium catalyzes the oxygenation of 1,1-dimethylcyclopropane in the presence of O₂ and NADH to (1-methylcyclopropyl)methanol(81%), 3-methyl-3-buten-1-ol (6%), and 1-methylbutanol (13%). Oxygenation by ¹⁸O₂ using the purified enzyme proceeds with incorporation of ¹⁸O into the products. Inasmuch as methane monooxygenase catalyzes the insertion of O from O₂ into a C-H bond of alkanes, (1-methylcyclopropyl)methanol appears to be a conventional oxygenation product. 3-Methyl-3-buten-1-ol is a rearrangement product that can be rationalized on the basis that enzymic oxygenation of 1,1-dimethylcyclopropane proceeds via the (1-methylcyclopropyl)carbinyl radical, which is expected to undergo rearrangement with ring opening to the homoallylic 3-methyl-3-buten-1-yl radical in competition with conventional with ring opening to the homoallylic 3-methyl-3-butenyl-1-yl radical in competition with conventional oxygenation. Oxygenation of the latter radical gives 3-methyl-3-buten-1-ol. 1-Methylcyclobutanol is a ring-expansion product, whose formation is best explained on the basis that the 1-methylcyclobutyl tertiary carbocation is an oxygenation intermediate. This cation would result from rearrangements of carbocations derived by 1-electron oxidation of either radical intermediate. The fact that both 3-methyl-3-buten-1-ol and 1-methylcyclobutanol are produced suggests that the oxygenation mechanism involves both radical and carbocationic intermediates. Radicals and carbocations can both be intermediates if they are connected by an electron-transfer step. A reasonable reaction sequence is one in which the cofactor (μ-oxo)diiron reacts with O₂ and 2-electrons to generate a H atom-abstracting species and an oxidizing agent. The H-abstracting species might be the enzymic radical or another species generated by the Fe complex and O₂. Oxygenation then could proceed by abstraction for a H atom from the substrate to form a radical, followed by electron transfer from the radical to the oxidizing species to form a carbocation. The carbocation would be quenched by O associated with the oxygenation cofactor to generate the product.

Biochemistry published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, COA of Formula: C5H10O.

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

Moe, Luke A. published the artcileRemarkable Aliphatic Hydroxylation by the Diiron Enzyme Toluene 4-Monooxygenase in Reactions with Radical or Cation Diagnostic Probes Norcarane, 1,1-Dimethylcyclopropane, and 1,1-Diethylcyclopropane, Application of 1-Methylcyclobutan-1-ol, the publication is Biochemistry (2004), 43(50), 15688-15701, database is CAplus and MEDLINE.

Toluene 4-monooxygenase (T4MO) catalyzes the hydroxylation of toluene to yield 96% p-cresol. This diiron enzyme complex was used to oxidize norcarane (bicyclo[4.1.0]heptane), 1,1-dimethylcyclopropane, and 1,1-diethylcyclopropane, substrate analogs that can undergo diagnostic reactions upon the production of transient radical or cationic intermediates. Norcarane closely matches the shape and volume of the natural substrate toluene. Reaction of isoforms of the hydroxylase component of T4MO (T4moH) with different regiospecificities for toluene hydroxylation (k_cat ≈ 1.9-2.3 s^-1 and coupling efficiency ≈ 81-96%) revealed similar catalytic parameters for norcarane oxidation (k_cat ≈ 0.3-0.5 s^-1 and coupling efficiency ≈ 72%). The products included variable amounts of the un-rearranged isomeric norcaranols and cyclohex-2-enyl methanol, a product attributed to rearrangement of a radical oxidation intermediate. A ring-expansion product derived from the norcaranyl C-2 cation, cyclohept-3-enol, was not produced by either the natural enzyme or any of the T4moH isoforms tested. Comparative studies of 1,1-dimethylcyclopropane and 1,1-diethylcyclopropane, diagnostic substrates with differences in size and with ∼50-fold slower k_cat values, gave products consistent with both radical rearrangement and cation ring expansion. Examination of the isotopic enrichment of the incorporated O-atoms for all products revealed high-fidelity incorporation of an O-atom from O₂ in the un-rearranged and radical-rearranged products, while the O-atom found in the cation ring-expansion products was predominantly obtained by reaction with H₂O. The results show a divergence of radical and cation pathways for T4moH-mediated hydroxylation that can be dissected by diagnostic substrate probe rearrangements and by changes in the source of oxygen used for substrate oxygenation.

Biochemistry published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, Application of 1-Methylcyclobutan-1-ol.

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

Burgers, Peter C. published the artcileMetastable ion studies. XIII. The measurement of appearance energies of metastable peaks, Product Details of C5H10O, the publication is Organic Mass Spectrometry (1982), 17(3), 123-6, database is CAplus.

A simple, accurate, and reproducible method for measuring the appearance energy of a metastable peak is reported. The method involves comparison of the metastable-peak intensity with that of a standard metastable peak, over a small range of ionizing electron energies above their onsets. Six fragmentation processes whose reaction energetics are well established, e.g., AcOMe→ MeC⁺O + OMe•, provided suitable metastable peaks for calibration. Results for fragmentations having large kinetic shifts, e.g., PhBr → [Ph]⁺ + Br•, and for primary and secondary ion decompositions are reported.

Organic Mass Spectrometry published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, Product Details of C5H10O.

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

Brady, Stephen F. published the artcileSome novel, acid-labile amine protecting groups, SDS of cas: 20117-47-9, the publication is Journal of Organic Chemistry (1977), 42(1), 143-6, database is CAplus and MEDLINE.

RO2C-Phe-OH [I; R = cyclopropylmethyl (CP), 1-methylcyclobutyl (MCB), cyclobutyl, 1-methylcyclohexyl, 1-cyclopropylethyl] and R1O2C-Phe-Ala-OMe (R1 = CP, MCB) were prepared After 48 hr in 50% HOAc, >99% of MCBO2C-Phe-OH (II) remained unchanged, whereas under the same conditions 10-15% of BOC was cleaved from BOC-Phe-OH. However, the complete removal of MCBO2C was achieved by treating II with CF3CO2H at 25° for 30 min. ROH were treated with COCl2 to give RO2CCl which were treated with phenylalanine or with H-Phe-OMe and saponified to give I.

Journal of Organic Chemistry published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, SDS of cas: 20117-47-9.

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

Creary, Xavier published the artcileγ-Trimethylsilylcyclobutyl Carbocation Stabilization, COA of Formula: C5H10O, the publication is Journal of Organic Chemistry (2015), 80(3), 1781-1788, database is CAplus and MEDLINE.

Isomeric 3-trimethylsilyl-1-arylcyclobutyl carbocations, where the cross-ring 3-trimethylsilyl group has the potential to interact with the cationic center, were generated under solvolytic conditions. When the cationic center can interact with the rear lobe of the carbon-silicon bond, rate enhancements become progressively larger as the substituent on the aryl group becomes more electron-withdrawing. When the potential interaction with the trimethylsilyl group is via a front lobe interaction, there is minimal rate enhancement over the range of substituents. Computational studies also were carried out on these cations. Calculated trimethylsilyl stabilization energies progressively increase with electron-withdrawing character of the aryl groups when the trimethylsilyl interaction is via the rear lobe. But there are minimal changes in stabilization energies when the potential trimethylsilyl interaction is via the front lobe of the carbon-silicon bond. These computational studies, along with the solvolytic studies, point to a significant rear lobe 3-trimethylsilyl stabilization of arylcyclobutyl cations. They also argue against any front lobe stabilization of the isomeric arylcyclobutyl cations.

Journal of Organic Chemistry published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, COA of Formula: C5H10O.

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