40571-86-6 Archives - Alcohols-buliding-blocks

Chakraborti, Asit K. et al. published their research in Tetrahedron in 2004 | CAS: 40571-86-6

Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6) belongs to alcohols. The oxygen atom of the strongly polarized O鈥旽 bond of an alcohol pulls electron density away from the hydrogen atom. This polarized hydrogen, which bears a partial positive charge, can form a hydrogen bond with a pair of nonbonding electrons on another oxygen atom. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.HPLC of Formula: 40571-86-6

Scope and limitations of montmorillonite K 10 catalyzed opening of epoxide rings by amines was written by Chakraborti, Asit K.;Kondaskar, Atul;Rudrawar, Santosh. And the article was included in Tetrahedron in 2004.HPLC of Formula: 40571-86-6 This article mentions the following:

Montmorillonite K 10 efficiently catalyzes the opening of epoxide rings by amines in high yields with excellent regio- and diastereoselectivities under solvent-free conditions at room temperature affording an improved process for synthesis of 2-amino alcs. Reaction of cyclohexene oxide with aryl/alkyl amines leads to the formation of trans-2-aryl/alkylaminocyclohexanols. For unsym. epoxides, the regioselectivity is controlled by the electronic and steric factors associated with the epoxide and the amine. Selective nucleophilic attack at the benzylic carbon of styrene oxide takes place with aromatic amines, whereas, aliphatic amines exhibit preferential nucleophilic attack at the terminal carbon. Aniline reacts selectively at the less hindered carbon of other unsym. epoxides. The difference in the internal strain energy of the epoxide ring in cycloalkene oxides and alkene oxides led to selective nucleophilic opening of cyclohexene oxide by aniline in the presence of styrene oxide. Due to the chelation effect, selective activation of the epoxide ring in 3-phenoxypropylene oxide takes place in the presence of styrene oxide leading to preferential cleavage of the epoxide ring in 3-phenoxypropylene oxide by aniline. In the experiment, the researchers used many compounds, for example, Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6HPLC of Formula: 40571-86-6).

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Kovar, Jan et al. published their research in Chemicke Listy pro Vedu a Prumysl in 1958 | CAS: 40571-86-6

Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. A multistep synthesis may use Grignard-like reactions to form an alcohol with the desired carbon structure, followed by reactions to convert the hydroxyl group of the alcohol to the desired functionality.Synthetic Route of C13H19NO

Configuration of nitrogen-containing compounds. VI. Configuration of substituted 2-aminocyclohexanols was written by Kovar, Jan;Blaha, Karel. And the article was included in Chemicke Listy pro Vedu a Prumysl in 1958.Synthetic Route of C13H19NO This article mentions the following:

The rate of solvolysis of N-R-substituted-2-(p-nitrophenyl)-4,5-tetra-methylenoxazolidine (I) obtained by condensing N-R-substituted-2-aminocyclohexanols (II) with p-O₂NC₆H₄CHO was studied in regard to the steric structure of the starting amino alcs. trans-II (R = Me) obtained in 8.5 g. yield by shaking 24 hrs. a mixture of 13.4 g. trans-2-chlorocyclohexanol and 15 ml. solution containing 0.15 mole NH₂Me, adding 50 ml. N HCl, extracting undissolved oil with Et₂O, alkalizing the aqueous solution with NaOH, extracting with 4:1 CHCl₃-Et₂O, and evaporating the solvent gave an oily residue, b₂₁ 113掳, which crystallized, m. 22-4掳; HCl salt, m. 121掳 (9:1 Me₂CO-MeOH). Heating a solution of 4 g. trans-II (R = H) and 3.2 g. PhCH₂NH₂ in 7 ml. EtOH 8 hrs. to 145-55掳 in a sealed tube, dissolving the crystalline product in 50 ml. H₂O, and working up as above gave 2.0 g. trans-II (R = PhCH₂) b_0.6 125-7掳, m. 73掳 (petr. ether); picrate, m. 134-5掳 (50% EtOH); HCl salt, m. 204-5掳 (Me₂CO-EtOH 9:1); trans-N-benzoyl derivative (III) obtained in 77% yield by the usual method gave crystals, m. 116.5-17.5掳 (C₆H₆-petr. ether). Hydrogenating 27 g. 慰-AcNHC₆H₄OH over Raney Co in EtOH at 150-60掳 and 100 atm. 12 hrs., filtering off the catalyst, evaporating the solvent in vacuo, and treating the residue with 10 ml. Me₂CO gave 5.8 g. crystals of cis-II (R = Ac) (IV), m. 143-4掳. IV (4.7 g.) boiled 2 hrs. with 2.33N HCl and worked up as usual gave 4.3 g. HCl salt of cis-II (R = H), m. 186-6.5掳; free base, m. 73-5掳. cis-II (R = Me) was obtained according to Mousseron, et al. (C.A. 47, 9319a), m. 38-40掳; HCl salt, m. 205-6掳 (1:1 EtOH-Me₂CO); picrate, m. 141-2掳 (H₂O). cis-II (R = PhCH₂) was obtained by heating a solution of III in SOCl₂ 2.5 hrs. to 60掳, pouring the product into Et₂O, and refluxing the undissolved portion 5 hrs. with 10% HCl, or by distilling a solution of 747 mg. cis-II (R = H) and 1.5 g. PhCHO in 25 ml. C₆H₆ with simultaneous dropwise addition of C₆H₆, dissolving the residue in Et₂O, and boiling 6 hrs. with 1 g. LiAlH₄ to give crystalline HCl salt, m. 248-50掳 (1:1 EtOH-Me₂CO); free base, m. 67掳 (petr. ether); picrate, m. 157-8掳 (H₂O). The following I were obtained by heating slowly to boiling equivalent amounts of II and p-O₂NC₆H₄CHO in PhCl (50 ml. per 10 millimoles with continuous removal of H₂O. The products were crystallized from petr. ether or petr. ether-C₆H₆: cis-I (R = H), m. 73-3.5掳 (yield 93%); cis-I (R = Me), m. 68-9掳 (82%); cis-I (R = PhCH₂), m. 59-61掳 (94%); trans-I (R = H), m. 127掳 (65%); trans-I (R = Me), m. 77-8掳 (78%); trans-I (R = PhCH₂), m. 97.5-99掳 (50%). Treatment of I with 2,4-(O₂N)₂C₆H₃NHNH ₂ in EtOH at 24掳 catalyzed with H₂SO₄ brought about opening of the ring. Its rate was followed by determining gravimetrically the separated 4-O₂NC₆H₄CH:NNHC₆H₃(NO₂)₂-2,4. The reaction constants of the cis and trans isomers are, resp.: I (R = H) 9.81 脳 10^-3, 4.7 脳 10^-2; I (R = Me) 8.12 脳 10^-4, 8.0 脳 10^-2; I (R = PhCH₂) 1.31 脳 10^-3, 1 脳 10^-1. In the experiment, the researchers used many compounds, for example, Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6Synthetic Route of C13H19NO).

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Mahadevan, Viswanath et al. published their research in Angewandte Chemie, International Edition in 2002 | CAS: 40571-86-6

Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R鈥昈鈭?. For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Quality Control of Trans-2-(benzylamino)cyclohexanol

[Lewis acid]⁺[Co(CO)₄]^– complexes: A versatile class of catalysts for carbonylative ring expansion of epoxides and aziridines was written by Mahadevan, Viswanath;Getzler, Yutan D. Y. L.;Coates, Geoffrey W.. And the article was included in Angewandte Chemie, International Edition in 2002.Quality Control of Trans-2-(benzylamino)cyclohexanol This article mentions the following:

Efficient carbonyl insertion into C-O and C-N bonds using [Lewis acid]-⁺[Co(CO)₄]^– complexes [Cp₂Ti(thf)₂][Co(CO)₄] 1 and [(salph)Al(thf)₂][Co(CO)₄] 2 [salph = N,N’-bis(3,5-di-tert-butylsalicylidene)phenylenediamine] gives regio- and stereoselective carbonylation of a variety of epoxides and aziridines to yield 尾-lactones and 尾-lactams, resp. Both transformations are proposed to occur by the same mechanism, yielding products with inversion of configuration at the site of CO insertion. In the experiment, the researchers used many compounds, for example, Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6Quality Control of Trans-2-(benzylamino)cyclohexanol).

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Chini, Marco et al. published their research in Tetrahedron Letters in 1990 | CAS: 40571-86-6

Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Reference of 40571-86-6

Metal salts as new catalysts for mild and efficient aminolysis of oxiranes was written by Chini, Marco;Crotti, Paolo;Macchia, Franco. And the article was included in Tetrahedron Letters in 1990.Reference of 40571-86-6 This article mentions the following:

A new, simple, efficient, inexpensive method for aminolysis of 1,2-epoxides, by means of metal salts, is described. The reactions proceed under mild conditions in MeCN to afford 尾-amino alcs. with complete antistereoselectivity and generally high regioselectivity. In the experiment, the researchers used many compounds, for example, Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6Reference of 40571-86-6).

Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Reference of 40571-86-6

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Kovar, Jan et al. published their research in Chemicke Listy pro Vedu a Prumysl in 1958 | CAS: 40571-86-6

The rate of solvolysis of N-R-substituted-2-(p-nitrophenyl)-4,5-tetra-methylenoxazolidine (I) obtained by condensing N-R-substituted-2-aminocyclohexanols (II) with p-O₂NC₆H₄CHO was studied in regard to the steric structure of the starting amino alcs. trans-II (R = Me) obtained in 8.5 g. yield by shaking 24 hrs. a mixture of 13.4 g. trans-2-chlorocyclohexanol and 15 ml. solution containing 0.15 mole NH₂Me, adding 50 ml. N HCl, extracting undissolved oil with Et₂O, alkalizing the aqueous solution with NaOH, extracting with 4:1 CHCl₃-Et₂O, and evaporating the solvent gave an oily residue, b₂₁ 113°, which crystallized, m. 22-4°; HCl salt, m. 121° (9:1 Me₂CO-MeOH). Heating a solution of 4 g. trans-II (R = H) and 3.2 g. PhCH₂NH₂ in 7 ml. EtOH 8 hrs. to 145-55° in a sealed tube, dissolving the crystalline product in 50 ml. H₂O, and working up as above gave 2.0 g. trans-II (R = PhCH₂) b_0.6 125-7°, m. 73° (petr. ether); picrate, m. 134-5° (50% EtOH); HCl salt, m. 204-5° (Me₂CO-EtOH 9:1); trans-N-benzoyl derivative (III) obtained in 77% yield by the usual method gave crystals, m. 116.5-17.5° (C₆H₆-petr. ether). Hydrogenating 27 g. ο-AcNHC₆H₄OH over Raney Co in EtOH at 150-60° and 100 atm. 12 hrs., filtering off the catalyst, evaporating the solvent in vacuo, and treating the residue with 10 ml. Me₂CO gave 5.8 g. crystals of cis-II (R = Ac) (IV), m. 143-4°. IV (4.7 g.) boiled 2 hrs. with 2.33N HCl and worked up as usual gave 4.3 g. HCl salt of cis-II (R = H), m. 186-6.5°; free base, m. 73-5°. cis-II (R = Me) was obtained according to Mousseron, et al. (C.A. 47, 9319a), m. 38-40°; HCl salt, m. 205-6° (1:1 EtOH-Me₂CO); picrate, m. 141-2° (H₂O). cis-II (R = PhCH₂) was obtained by heating a solution of III in SOCl₂ 2.5 hrs. to 60°, pouring the product into Et₂O, and refluxing the undissolved portion 5 hrs. with 10% HCl, or by distilling a solution of 747 mg. cis-II (R = H) and 1.5 g. PhCHO in 25 ml. C₆H₆ with simultaneous dropwise addition of C₆H₆, dissolving the residue in Et₂O, and boiling 6 hrs. with 1 g. LiAlH₄ to give crystalline HCl salt, m. 248-50° (1:1 EtOH-Me₂CO); free base, m. 67° (petr. ether); picrate, m. 157-8° (H₂O). The following I were obtained by heating slowly to boiling equivalent amounts of II and p-O₂NC₆H₄CHO in PhCl (50 ml. per 10 millimoles with continuous removal of H₂O. The products were crystallized from petr. ether or petr. ether-C₆H₆: cis-I (R = H), m. 73-3.5° (yield 93%); cis-I (R = Me), m. 68-9° (82%); cis-I (R = PhCH₂), m. 59-61° (94%); trans-I (R = H), m. 127° (65%); trans-I (R = Me), m. 77-8° (78%); trans-I (R = PhCH₂), m. 97.5-99° (50%). Treatment of I with 2,4-(O₂N)₂C₆H₃NHNH ₂ in EtOH at 24° catalyzed with H₂SO₄ brought about opening of the ring. Its rate was followed by determining gravimetrically the separated 4-O₂NC₆H₄CH:NNHC₆H₃(NO₂)₂-2,4. The reaction constants of the cis and trans isomers are, resp.: I (R = H) 9.81 × 10^-3, 4.7 × 10^-2; I (R = Me) 8.12 × 10^-4, 8.0 × 10^-2; I (R = PhCH₂) 1.31 × 10^-3, 1 × 10^-1. In the experiment, the researchers used many compounds, for example, Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6Synthetic Route of C13H19NO).

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Mahadevan, Viswanath et al. published their research in Angewandte Chemie, International Edition in 2002 | CAS: 40571-86-6

Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Quality Control of Trans-2-(benzylamino)cyclohexanol

Efficient carbonyl insertion into C-O and C-N bonds using [Lewis acid]-⁺[Co(CO)₄]^– complexes [Cp₂Ti(thf)₂][Co(CO)₄] 1 and [(salph)Al(thf)₂][Co(CO)₄] 2 [salph = N,N’-bis(3,5-di-tert-butylsalicylidene)phenylenediamine] gives regio- and stereoselective carbonylation of a variety of epoxides and aziridines to yield β-lactones and β-lactams, resp. Both transformations are proposed to occur by the same mechanism, yielding products with inversion of configuration at the site of CO insertion. In the experiment, the researchers used many compounds, for example, Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6Quality Control of Trans-2-(benzylamino)cyclohexanol).

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Chini, Marco et al. published their research in Tetrahedron Letters in 1990 | CAS: 40571-86-6

Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Reference of 40571-86-6

A new, simple, efficient, inexpensive method for aminolysis of 1,2-epoxides, by means of metal salts, is described. The reactions proceed under mild conditions in MeCN to afford β-amino alcs. with complete antistereoselectivity and generally high regioselectivity. In the experiment, the researchers used many compounds, for example, Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6Reference of 40571-86-6).

Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Reference of 40571-86-6

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Abaee, M. Saeed et al. published their research in Ultrasonics Sonochemistry in 2008 | CAS: 40571-86-6

Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6) belongs to alcohols. The oxygen atom of the strongly polarized O―H bond of an alcohol pulls electron density away from the hydrogen atom. This polarized hydrogen, which bears a partial positive charge, can form a hydrogen bond with a pair of nonbonding electrons on another oxygen atom. Under carefully controlled conditions, simple alcohols can undergo intermolecular dehydration to give ethers. This reaction is effective only with methanol, ethanol, and other simple primary alcohols.Formula: C13H19NO

Ultrasound-promoted aminolysis of epoxides in aqueous media. A rapid procedure with no pH adjustment for additive-free synthesis of β-aminoalcohols was written by Abaee, M. Saeed;Hamidi, Vahid;Mojtahedi, Mohammad M.. And the article was included in Ultrasonics Sonochemistry in 2008.Formula: C13H19NO This article mentions the following:

An efficient and environmentally friendly procedure promoted by ultrasound irradiation was developed for stereoselective ring opening of various epoxides with aromatic and aliphatic amines under aqueous conditions in the presence of no catalyst or additive. Chemoselectivity of the protocol was shown by competition of piperidine and aniline to react with different epoxides resulting in exclusive formation of the resp. products of piperidine. In the experiment, the researchers used many compounds, for example, Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6Formula: C13H19NO).

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Takeuchi, Yuki et al. published their research in Molecules in 2020 | CAS: 40571-86-6

Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. Converting an alcohol to an alkene requires removal of the hydroxyl group and a hydrogen atom on the neighbouring carbon atom. Dehydrations are most commonly carried out by warming the alcohol in the presence of a strong dehydrating acid, such as concentrated sulfuric acid.Recommanded Product: 40571-86-6

Asymmetric amination of meso-epoxide with vegetable powder as a low-toxicity catalyst was written by Takeuchi, Yuki;Asano, Tatsuhiro;Tsuzaki, Kazuya;Wada, Koichi;Kurata, Hiroyuki. And the article was included in Molecules in 2020.Recommanded Product: 40571-86-6 This article mentions the following:

This paper describes the scope and limitation of substrates subjected to asym. amination with epoxides catalyzed by a soluble soybean polysaccharide (Soyafibe S-DN), which we recently discovered from the reaction of 1,2-epoxycyclohexane with cyclopropylamine. Various meso-epoxides reacted with various amines afforded the corresponding products with good enantiomeric selectivity. Since it was found that pectin was found to have a catalytic ability after screening com. available polysaccharides, we studied 33 different vegetable powders having pectic substances, and we found that many vegetable powders showed catalytic ability. These results should guide in using vegetable components as low-toxic catalysts for the production of pharmaceuticals. In the experiment, the researchers used many compounds, for example, Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6Recommanded Product: 40571-86-6).

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Sources of common compounds: 40571-86-6

The chemical industry reduces the impact on the environment during synthesis 40571-86-6, I believe this compound will play a more active role in future production and life.

Synthetic Route of 40571-86-6, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.40571-86-6, name is Trans-2-(benzylamino)cyclohexanol, molecular formula is C13H19NO, molecular weight is 205.2961, as common compound, the synthetic route is as follows.

General procedure: In a typical reaction, 90mL dry acetonitrile solution of tetrabutylammonium tetrafluoroborate(0.1 M) as the supporting electrolyte in an undivided cell fitted with a sacrificial magnesium rod as an anode and a stainless steel grid (20 cm2) as the cathode was subjected to electrolysis at a constant current density (I = 80 mA/cm?2). The cell was cooled to ?20°C by immersing in the Lauder refrigerating system. During the electrolysis, the system was maintained under an inert atmosphere by continuous bubbling of nitrogen. The electrolysis was stopped after the formationof two equivalents of cyanomethyl anion with respect to the beta-aminoalcohol derivatives(10 mmol, Q = 193 C). Then, 1.1 equivalent of carbon disulfide is added.The solution was removed from the cooling bath and was allowed to reach room temperature and kept under continuous stirring for 12 hours to ensure completion of the reaction. The excess of acetonitrile was removed using a rotatory evaporator, the residue was washed with water and the product was extracted three times with diethyl ether. The organic layer was washed with 20mL of water and dried over anhydrous magnesium sulfate. The solvent was removed and the residue was purified by column chromatography on silica gel 60 using a mixture of ethyl acetate/hexane (3:7) as the eluent. All the products were obtained as solids. They were characterized by 1H and 13C NMR spectroscopy, IR spectroscopy, EI mass spectrometry andelementary analysis.

The chemical industry reduces the impact on the environment during synthesis 40571-86-6, I believe this compound will play a more active role in future production and life.

Reference:
Article; Medini, Hayet; Mekni, Nejib Hussein; Boujlel, Khaled; Journal of Sulfur Chemistry; vol. 36; 6; (2015); p. 653 – 659;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts