Tag: M.W=50-100

Cox, Eugene F. published the artcileSmall-ring compounds. XXXIV. Carbonium ion reactions of 1-methylcyclobutyl-, (1-methylcyclopropyl)carbinyl, and (β-methylallyl)carbinyl derivatives, Name: 1-Methylcyclobutan-1-ol, the publication is Journal of the American Chemical Society (1961), 2719-24, database is CAplus.

cf. CA 46, 1453a, 55, 22160d. (1-Methylcyclopropyl)carbinyl chloride (I) solvolyzed in 50% aqueous EtOH about 10 times faster than 1-methylcyclobutyl chloride (II) and as fast as Me₃CCl. Treatment of (1-methylcyclopropyl)carbinylamine (III) and 1-methylcyclobutylamine (IV) with HNO₂ gave only 1-methylcyclobutanol (V). CH₂:CMeCH₂CH₂NH₂ (VI) gave V as the only cyclic product. About 3% of the C¹⁴ content of V from the deamination of III-α-C¹⁴ (VII) was found at the 3-position. These results were interpretable in terms of classical carbonium ions and(or) substituted bicyclobutonium ion intermediates with fairly localized pos. charges. CH₂: CMeCO₂Me added to CH₂N₂-Et₂O at 0°, the resulting pyrazoline (90%) pyrolyzed in small quantities, and the combined crude product distilled yielded 316 g. crude Me ester (VIII) of 1-methylcyclopropanecarboxylic acid (IX), containing some unsaturated material, which treated in petr. ether with slightly alk. 0.25M KMnO₄ at 0° and worked up gave pure VIII, b_60.4-65.6 55.9-7.1°, n²⁵_D 1.4192-1.4193. The VIII hydrolyzed gave 90% IX, m. 32.4-4.3° (all m.ps. corrected); p-bromophenacyl ester m. 64.1-5.0° (50% aqueous EtOH); anilide m. 100.5-1.6° (50% aqueous EtOH), 100.6-1.3° (hexane). The Ag salt of IX in Freon-12 treated with Br gave 71% 1-methylcyclopropyl bromide (X), b₇₄₀ 77.2-8.0°, n²⁵_D 1.44711.4474. A small amount of X converted to the Grignard reagent and treated with PhNCO gave 1-methylcyclopropanecarboxanilide, m. 99.2-100.1°. IX was converted into 72% amide, m. 145.7-6.9°. CH₂:CMeCN with CH₂N₂ in Et₂O yielded 1-methylcyclopropanecarbonitrile (XI), b₇₆₅ 127.7-8.5°, n²⁵_D 1.4128. VIII reduced with LiAlH₄ gave (1-methylcyclopropyl)carbinol, b₇₃₉ 125.8-6.3°, n²⁵_D 1.42901.4292; 3,5-dinitrobenzoate m. 88.9-90.7° (C₆H₆-cyclohexane). XI reduced with Na-EtOH gave 56% III, b₇₆₄ 95.0-6.8°, n²⁵_D 1.4269. XI reduced with LiAlH₄ in Et₂O gave 70% III, b₇₆₁ 94.3-6.1°, n²⁵_D 1.4207-1.4273; N-phenyl-N’-(1-methylcyclopropylcarbinyl)thiourea m. 112.7-13.5° (95% EtOH). Me₂C(CH₂OH)₂ treated with PBr₃ and the dibromide cyclized gave 1,1-dimethylcyclopropane (XII), b₇₃₈ 19.0-20.0°. XII (74.5 g.) chlorinated by the method of Robert and Mazur (loc. cit.) gave 102 g. mixture of 49% I, 16% II, 14% CH₂: CHMeCH₂Cl, and 32% unreactive chloride, which carefully refractionated gave pure I, b₇₃₅, 83.0-3.9°, n²⁵_D 1.4045-1.4052. The H₂SO₄-catalyzed addition of H₂O to methylenecyclobutane (XIII), b₇₃₉ 41.0-2.0°, yielded 68% V, b₇₄₆ 117.8-18.3°, n²⁵_D 1.4332-1.4336. The hydrolysis of II yielded 40% V, b₇₅₆ 117.1-18.9°, n²⁵_D 1.4329. Cyclobutanone with MeMgBr gave 67% V, b₇₆₅ 118.3°, n²⁵_D 1.4332. HCl added to XIII yielded 81% II, b₇₄₂ 90.8-1.3°, n²⁵_D 1.4283-1.4287. MeCN (9.0 g.), 100 cc. glacial AcOH, and 20 cc. concentrated H₂SO₄ treated with stirring with 13.6 g. XIII, stirred 1 hr. at 20°, cooled, diluted with 300 cc. H₂O, basified with Na₂CO₃, and extracted with Et₂O, and the extract worked up yielded 17.7 g. N-(1-methylcyclobutyl)acetamide (XIV). XIV (10.0 g.) and 400 cc. 4N KOH in (CH₂OH)₂ refluxed 48 hrs. and continuously extracted with Et₂O yielded 3.1 g. IV, b₇₆₄ 85.5-6.0°, n²⁵_D 1.4200. XIII (13.6 g.), 11.0 g. 90% NaCN, and 25 cc. glacial AcOH treated at 0° with 25 cc. AcOH and 50 g. concentrated H₂SO₄ during 25 min., stirred 3 hrs. at 0°, 1 hr. at room temperature, and 45 min. at 55°, kept overnight at room temperature, treated slowly with stirring with 120 g. NaOH in 250 cc. H₂O, refluxed 8 hrs., and steam distilled, and the distillate (250 cc.) extracted 18 hrs. with Et₂O yielded 8.03 g. IV, b₇₄₅ 84.0-4.7°, n²⁵_D 1.4292-1.4293; N-phenyl-N’-(1-methylcyclobutyl)thiourea, m. 135.3-5.8° (aqueous EtOH). CH₂:CMeCH₂CH₂Cl was converted by the method of Kharasch and Fuchs (CA 38, 6281⁹) in 35% yield to CH₂:CMeCH₂CH₂OH (XV), b₇₄₁ 127.9-30.4°, n²⁵_D 1.43051.4312; 1-naphthylurethan m. 66.7-7.3° (petr. ether). XV (8.61 g.), 25 cc. dry Et₂O, 18.5 g. Bu₃N treated with stirring at 0° with 11.9 g. SOCl₂ during 3 hrs. gave CH₂:CMeCH₂CH₂Cl (XVI), b₇₃₉, 101.0-2.7°, n²⁵_D 1.4301-4305. XVI with K phthalimide in HCONMe₂ yielded 85% N-I-(3-methyl-3-butenyl)phthalimide (XVII), m. 51.2-2.8°. Hydrazinolysis of XVII in HClO₄ gave 26% VI, b₁₀₁ 47.6-8.5°, n²⁵_D 1.4288. CH₂:CMeCHO with MeMgBr yielded CH₂:CMeCH(OH)Me, b_59.9-60.4 54.6-6.8°, n²⁵_D 1.4241-1.4242. 3-Methyl-3-carbomethoxy-l-pyrazoline pyrolyzed and the high-boiling fractions of the product redistilled gave Me tiglate, b₇₄₀ 136.9-7.1°, n²⁵_D 1.4338, which reduced with LiAlH₄ yielded about 40% MeCH:CMeCH₂OH, b. 137.6-7.9°, n²⁵_D 1.4386-1.4401. III (12.8 g.) in 50 cc. H₂O and 180 cc. 1.0N HClO₄ treated during 0.5 hr. with stirring with 30 g. NaNO₂ in 100 cc. H₂O, heated 1 hr. at 50-65 mm., and steam-distilled, the aqueous phase of the distillate saturated with K₂CO₃ and extracted with Et₂O, and the combined organic layer and extract distilled gave 0.72 g. V. The Grignard reagent from X carbonated in vacuo with C¹⁴O₂, diluted with inactive IX, and distilled gave IX-α-C¹⁴, b_19.2-19.4 96.6-7.4° (radioactive yield 88%), which was converted to the amide and further by reduction with LiAlH₄ to 51% VII. VII treated in AcOH with NaNO₂ in portions, poured into 20% aqueous NaOH, and extracted with Et₂O, and the resulting mixture of labeled alc. and acetate reduced with LiAlH₄ gave V. VII.HCl oxidized with alk. KMnO₄ and a portion of the resulting acid converted to the amide gave a material containing 0.128 microcuries/millimole; another portion of the acid was subjected to a Schmidt degradation and the resulting amine converted to the benzamide, m. 161.7-3.0°, containing 0.000-37 microcuries/millimoles, corresponding to 0.29% of the original activity. The rates of the solvolysis in 50% EtOH were determined for the following compds (reaction temperature, and k₁ × 10⁵/sec. given): cyclopropyl bromide, 130°, 0.26; X, 130°, 10.5; II, 50°, 61.7; II, 30°, 7.15; I, 30°, 69; XVI, 90°, 0.17.

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, Name: 1-Methylcyclobutan-1-ol.

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

Mahapatra, Mausumi published the artcileFormation of Induced-Fit Chiral Templates by Amino Acid-Functionalized Pd(111) Surfaces, SDS of cas: 57044-25-4, the publication is Journal of Physical Chemistry C (2015), 119(7), 3556-3563, database is CAplus.

Chiral probe mols., propylene oxide, and glycidol are used to measure the enantioselectivity of a range of amino acid-functionalized Pd(111) surfaces. Only those surfaces that contain tetrameric amino acid assemblies are found to be enantioselective, indicating that they act as chiral templates in which several modifiers operate in concert to form a chiral reaction pocket. It has previously been shown that the tetramers assemble from antiparallel anionic-zwitterionic dimers where three of the amino acids then undergo a concerted translational motion to form a more stable tetramer. However, d. functional theory calculations reveal that the most stable tetramer has a pocket that is too small to accommodate the chiral probes, while the more open antiparallel anionic-zwitterionic dimer structure provides sufficient space for the epoxide to adsorb enantioselectively on the most stable atop palladium adsorption site. Amino acid destabilization is confirmed by its lower desorption temperature measured in temperature-programmed desorption.

Journal of Physical Chemistry C published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, SDS of cas: 57044-25-4.

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

Brown, Pamela published the artcileβ-Lactamase-stable penicillins. Synthesis and structure-activity relationships of (Z)-alkyloxyimino penicillins; selection of BRL 44154, Safety of 1-Methylcyclobutan-1-ol, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1991), 881-91, database is CAplus.

A series of (Z)-2-alkyloxyimino-2-(2-aminothiazol-4-yl)acetamidopenicillins I (R = Me, Et, CHMe₂, CMe₃, cycloalkyl) were prepared New methodol. was developed to prepare tertiary alkyl oximes. High stability to β-lactamases and potent antibacterial activity have been achieved against Gram-pos. and certain Gram-neg. organisms. Activity against methicillin-resistant Staphylococcus aureus was an unexpected finding. BRL 44154 (I; R = cyclopentyl) has been selected for further study.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) 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, Safety of 1-Methylcyclobutan-1-ol.

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

Furkert, Daniel P. published the artcileNonsymmetrical Azocarbonamide Carboxylates as Effective Mitsunobu Reagents, Related Products of alcohols-buliding-blocks, the publication is European Journal of Organic Chemistry (2014), 2014(35), 7806-7809, database is CAplus.

The nonsym. Mitsunobu reagents possessing both dialkyl amide and ester substituents was developed. These new reagents were readily prepared in a single pot from inexpensive, com. available materials by using a scalable and environmentally friendly procedure. They were shown to exhibit activity parallel to that of di-Et azodicarboxylate/diisopropyl azodicarboxylate in a wide variety of Mitsunobu reactions. Importantly, the acyl hydrazine reaction byproducts were readily separable from the crude mixture by standard aqueous workup. In addition, the discovery of effective nonsym. Mitsunobu reagents offers new directions for the ongoing development of this important reaction.

European Journal of Organic Chemistry published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Related Products of alcohols-buliding-blocks.

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

Lewin, Anita H. published the artcileSynthesis and Characterization of the Selective, Reversible PKC_β Inhibitor (9S)-9-[(Dimethylamino)methyl]-6,7,10,11-tetrahydro-9H,18H-5,21:12,17-dimethenodibenzo[e,k]pyrrolo[3,4-h][1,4,13]oxadiazacyclohexadecine-18,20(19H)-dione, Ruboxistaurin (LY333531), SDS of cas: 57044-25-4, the publication is ACS Chemical Neuroscience (2019), 10(1), 246-251, database is CAplus and MEDLINE.

The demonstrated role of PKC_β in mediating amphetamine-stimulated dopamine efflux, which regulates amphetamine-induced dopamine transporter trafficking and activity, has promoted the research use of the selective, reversible PKC_β inhibitor (9S)-9-[(dimethylamino)methyl]-6,7,10,11-tetrahydro-9H,18H-5,21:12,17-dimethenodibenzo[e,k]pyrrolo[3,4-h][1,4,13]oxadiazacyclohexadecine-18,20(19H)-dione, ruboxistaurin. Despite the interest in development of ruboxistaurin as the mesylate monohydrate (Arxxant) for the treatment of diabetic retinopathy, macular edema, and nephropathy, several crucial details in physicochem. characterization were erroneous or missing. This report describes the synthesis and full characterization of ruboxistaurin free base (as a monohydrate), including X-ray crystallog. to confirm the absolute configuration, and of the mesylate salt, isolated as a hydrate containing 1.5 mol of water per mol.

ACS Chemical Neuroscience published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, SDS of cas: 57044-25-4.

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

Brown, Herbert C. published the artcileChemical effects of steric strain. VI. The effect of ring size on the rate of solvolysis of the 1-chloro-1-methylcycloalkane, Name: 1-Methylcyclobutan-1-ol, the publication is Journal of the American Chemical Society (1952), 1894-1902, database is CAplus.

cf. C.A. 48, 562d. Cyclic compounds undergoing reaction at a ring atom exhibit striking changes in reactivity with variation in ring size. These differences in chem. behavior are attributed to the changes in internal strain in the cyclic structures which accompany changes in the coördination number of the ring atom undergoing reaction (I-strain). 1-Chloro-1-methylcycloalkanes with C₄ to C₁₁ (inclusive), C₁₃, C₁₅, and C₁₇ rings were synthesized and the rates of solvolysis in 80% aqueous EtOH determined (k₁ at 25°). The rate of solvolysis for 1-chloro-1-methylcyclobutane (I) is relatively slow (0.00224/hr.), much slower than open-chain tertiary chlorides. 1-Chloro-1-methylcyclopentane (II) and -heptane (III) undergo solvolysis at a relatively fast rate (1.32 and 1.15/hr., resp.), whereas the corresponding cyclohexane (IV) derivative is slow (0.0106/hr.). The rates reach a maximum with the 8-membered ring (3.30/hr.) and then decrease to become essentially constant at 0.02-0.03/hr. with rings of 13 or more members. The results are in agreement with the predictions based upon the I-strain concept. Methylcyclopropane (V) was chlorinated photochemically at -20° in an attempt to synthesize 1-chloro-1-methylcyclopropane. The reaction yielded cyclopropylcarbinyl chloride (VI), b₇₃₆ 85.5-5.7°, n²⁰_D 1.4349, d₂₀ 0.981; VI via the Grignard reagent yielded an acid, b₂₀ 90-100, n²⁰_D 1.4350-1.4358; amide, m. 103-4°; p-bromophenacyl ester, m. 59.5-60.5°. VI in solvolysis studies behaved as a typical tertiary halide (0.00067/hr.). Reduction of pentaerythrityl bromide with Zn yielded 85-94% hydrocarbon mixture Methylenecyclobutane (b₇₄₄ 42.0°, n²⁰_D 1.4209) treated with HCl at 0° yielded 89% I, b₇₄₂ 89.5-91.4°, n²⁰_D 1.4310. I (9.2 g.) and 75 cc. water refluxed (the mixture was kept neutral by addition of 0.1N NaOH) and the product extracted with Et₂O yielded 54% 1-methylcyclobutanol, b₇₄₂ 116-18°, n²⁵_D 1.4333. HOCH₂CH₂CHMeOH (VII) and HBr at 100° yielded 67% CH₂BrCH₂CHBrMe (VIII), b₅₀ 87-92°, n²⁰_D 1.5080-1.5089. VII and PBr₃ yielded 77% VIII. VIII and Zn in aqueous EtOH yielded 70-88% V. Cyclopentanone (from adipic acid) with MeMgBr yielded 1-methylcyclopentanol (IX), b₇₄₅ 133-6°, m. 32-4°. IX yielded II, b₁₂₁ 66°, n²⁰_D 1.4467. Cyclohexanone yielded the tertiary alc. (X), b₂₉ 72-3.5°, n²⁰_D 1.4609. X yielded IV, b₁₀₀ 83-4°, n²⁰_D 1.4578. Cycloheptanone (b₇₄₇ 172-4°, n²⁰_D 1.4613) yielded 1-methylcycloheptanol (XI), b₂₀ 82-3.5°, n²⁰_D 1.4960. XI with dry HCl yielded 83% III, b_20.5 77-7.5°, n²⁰_D 1.4710. Cycloöctanone (4.06 g.) in 50 cc. Et₂O added MeMgI (from 14.2 g. MeI in 30 cc. Et₂O and 2.43 g. Mg in 15 cc. Et₂O) during 45 min., the mixture refluxed 4 hrs., titrated with saturated NH₄Cl, and the Et₂O evaporated in vacuo yielded 2 g. 1-methylcyclöctanol (XII), m. 34-6°. Distillation of XII yielded 1-methylcycloöctene (XIII), b₇₄₁ 159-64°, n²⁰_D 1.4710. XIII with HCl at 0° yielded the chloride b₄ 64-5°, n²⁰_D 1.4796. Di-Me azelate (b₁₀ 142-50°, n²⁰_D 1.4350-1.4363) by the method of Prelog, et al. (C.A. 42, 1893g), and Stoll, et al. (C.A. 42, 3741dh), yielded 26% crude acyloin fraction (XIV), b₁₂ 110-24°. XIV with Zn-HCl yielded 61% cyclononanone (XV), b₁₂ 92-6°, n⁴⁰_D 1.4682-1.4696. XV (9.8 g.) added during 2 hrs. to 0.21 mole Me Grignard reagent and the mixture refluxed 6 hrs. yielded 6.42 g. 1-methylcyclohexanol (XVI), m. 51-2°. XVI treated 2 hrs. at room temperature with HCl yielded 1-chloro-1-methylcyclononane. Sebacoin (b_0.1 75-85°, m. 36-7.5°, n⁵⁵_D 1.4788) on reduction yielded 73% ketone fraction (b₁₂ 95-112°), which on fractionation (b₁₂106-9°) m. 22-4°, n³⁰_D 1.4784. 1-Methylcyclodecanol (39% yield) m. 52.5-3.1°, Di-Me hendecanedioate (b₃139-50°, n²⁰_D 1.4379-91) yielded 61% acyloin fraction, b_0.08 88-93°, n⁵⁵_D 1.4803, m. 29-32°, which on reduction yielded 55% ketone fraction, b₁₂ 114-20°, n²⁰_D 1.4811; semicarbazone, m. 200-1°. Cycloundecanone (0.05 mole) and 0.15 mole MeMgI yielded 0.60 g. crystalline product, m. 128.5-9.5°, and 5.92 g. 1-methylcycloundecanol, m. 40-2°. For the larger rings, the ketone, its m.p., the tertiary alc., % yield, and m.p. are: cyclotridecanone, 30°, 1-methylcyclotridecanol, 92, 75.5-6.5°; cyclopentadecanone, 61.5-4.5°, 1-methyl-cyclopentadecanol, 80, 83.5-85°; cycloheptadecanone, 58-60°, 1-methylcycloheptadecanol, 92, 77.5-8.5°. -Am MgCl and EtOAc yielded the tertiary alc., b₂ 84.5-6.5°, n²⁰_D 1.4401; diamylmethylcarbinyl chloride was prepared

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, Name: 1-Methylcyclobutan-1-ol.

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

Bertranne, M. published the artcileStructure of C₄H₇O⁺ ions obtained by fragmentation of 1-methylcyclobutanol, SDS of cas: 20117-47-9, the publication is Tetrahedron Letters (1984), 25(2), 211-14, database is CAplus.

Fragmentation patterns from the mass spectra of the title compound demonstrate that the loss of Me leads competitively to three different ions: protonated cyclobutanone, [n-C₃H₇CO]⁺, and protonated Me vinyl ketone.

Tetrahedron 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 C5H10O, SDS of cas: 20117-47-9.

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

Luescher, Michael U. published the artcileEvidence for a Radical Mechanism in Cu(II)-Promoted SnAP Reactions, Formula: C4H11NO, the publication is Synlett (2019), 30(4), 464-470, database is CAplus.

Saturated nitrogen heterocycles could be found with increasing abundance in bioactive mols. despite a limited number of methods to access these scaffolds. However, the coupling of recently introduced SnAP [tin (Sn) amine protocol] reagents with a wide range of aldehydes and ketones had proven to be a reliable, practical, and versatile one-step approach to saturated N-heterocycles, e.g., I. While effective, the lack of mechanistic understanding limits efforts to develop new catalytic and enantioselective variants. To distinguish between a polar or radical mechanism, Lewis and Bronsted acids, radical trapping experiments, and radical clock SnAP reagents were assessed reinforcing the current understanding of the SnAP protocol as a radical cyclization.

Synlett published new progress about 96-20-8. 96-20-8 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 2-Aminobutan-1-ol, and the molecular formula is C4H11NO, Formula: C4H11NO.

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

Wang, Ya-Yi published the artcileOlefin Amine (OLA) Reagents for the Synthesis of Bridged Bicyclic and Spirocyclic Saturated N-Heterocycles by Catalytic Hydrogen Atom Transfer (HAT) Reactions, Quality Control of 96-20-8, the publication is Journal of the American Chemical Society (2019), 141(24), 9739-9745, database is CAplus and MEDLINE.

Using tandem imine formation and (diastereoselective) reductive cyclization reactions via iron- or manganese-catalyzed hydrogen-atom transfer, unsaturated amines (olefin-amine reagents, OLA) such as I, II, and III yielded spirocyclic, bridged, and fused saturated nitrogen heterocycles such as IV, V, and VI. A mechanism is proposed using a metal hydride hydrogen atom transfer to generate a C-centered radical that undergoes addition to an unactivated imine, leading to an N-centered radical; regeneration of the metal catalyst by O₂ and a second HAT to form the unprotected saturated N-heterocycle yields the observed products.

Journal of the American Chemical Society published new progress about 96-20-8. 96-20-8 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 2-Aminobutan-1-ol, and the molecular formula is C13H11NO, Quality Control of 96-20-8.

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

Alanthadka, Anitha published the artcileNickel-Catalyzed Double Dehydrogenative Coupling of Secondary Alcohols and β-Amino Alcohols To Access Substituted Pyrroles, SDS of cas: 96-20-8, the publication is Journal of Organic Chemistry (2019), 84(21), 13557-13564, database is CAplus and MEDLINE.

Herein, we demonstrate the first nickel-catalyzed double dehydrogenative condensation of secondary alcs. and β-amino alcs. in one pot to the pyrrole derivatives A series of 2,5- and 2,3,5-substituted pyrroles were obtained in â‰?3% yield, releasing water and hydrogen gas as byproducts. Initial mechanistic studies, including defined Ni catalyst, deuterium labeling experiments, quant. determination of hydrogen gas evaluation, and detection of water generation in the reaction mixture, were performed.

Journal of Organic Chemistry published new progress about 96-20-8. 96-20-8 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 2-Aminobutan-1-ol, and the molecular formula is C4H11NO, SDS of cas: 96-20-8.

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