Category: 120121-01-9

Efficient chiral synthesis by Saccharomyces cerevisiae spore encapsulation of Candida parapsilosis Glu228Ser/(S)-carbonyl reductase II and Bacillus sp. YX-1 glucose dehydrogenase in organic solvents was written by Rao, Jingxin;Zhang, Rongzhen;Liang, Hongbo;Gao, Xiao-Dong;Nakanishi, Hideki;Xu, Yan. And the article was included in Microbial Cell Factories in 2019.Safety of (R)-1-(3-Chlorophenyl)ethanol This article mentions the following:

Background: Saccharomyces cerevisiae AN120 osw2Δ spores were used as a host with good resistance to unfavorable environment. This work was undertaken to develop a new yeast spore-encapsulation of Candida parapsilosis Glu228Ser/(S)-carbonyl reductase II and Bacillus sp. YX-1 glucose dehydrogenase for efficient chiral synthesis in organic solvents. Results: The spore microencapsulation of E228S/SCR II and GDH in S. cerevisiae AN120 osw2Δ catalyzed (R)-phenylethanol in a good yield with an excellent enantioselectivity (up to 99%) within 4 h. It presented good resistance and catalytic functions under extreme temperature and pH conditions. The encapsulation produced several chiral products with over 70% yield and over 99% enantioselectivity in Et acetate after being recycled for 4-6 times. It increased substrate concentration over threefold and reduced the reaction time two to threefolds compared to the recombinant Escherichia coli containing E228S and glucose dehydrogenase. Conclusions: This work first described sustainable enantioselective synthesis without exogenous cofactors in organic solvents using yeast spore-microencapsulation of coupled alc. dehydrogenases.[Figure not available: see fulltext.]. In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9Safety of (R)-1-(3-Chlorophenyl)ethanol).

(R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9) belongs to alcohols. Similar to water, an alcohol can be pictured as having an sp3 hybridized tetrahedral oxygen atom with nonbonding pairs of electrons occupying two of the four sp3 hybrid orbitals. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Safety of (R)-1-(3-Chlorophenyl)ethanol

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Manganese-Catalyzed Asymmetric Hydrosilylation of Aryl Ketones was written by Ma, Xiaochen;Zuo, Ziqing;Liu, Guixia;Huang, Zheng. And the article was included in ACS Omega in 2017.SDS of cas: 120121-01-9 This article mentions the following:

Nonracemic (oxazolinyl)pyridinylimine manganese complexes I (R = i-Pr, Ph₂CH; R¹ = H, Me; R² = PhCH₂, i-Pr, t-Bu) were prepared as catalysts for the enantioselective hydrosilylation of aralkyl ketones. In the presence of I (R = Ph₂CH; R¹ = Me; R² = t-Bu), aralkyl ketones such as 4-R³C₆H₄COMe (R³ = Cl, i-Bu, t-Bu, cyclohexyl, n-Pr, MeO, Br, I, H) with Ph₃SiH and NaBHEt₃ in toluene to yield nonracemic benzylic alcs. such as (R)-4-R³C₆H₄CH(OH)Me (R³ = Cl, i-Bu, t-Bu, cyclohexyl, n-Pr, MeO, Br, I, H) in 48-99% yields and 66:34-96.5:3.5 er. The structure of I·2 CH₂Cl₂ (R = Ph₂CH; R¹ = Me; R² = t-Bu) was determined by X-ray crystallog. In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9SDS of cas: 120121-01-9).

(R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.SDS of cas: 120121-01-9

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Ruthenium(II)-Catalyzed Asymmetric Transfer Hydrogenation Using Unsymmetrical Vicinal Diamine-Based Ligands: Dramatic Substituent Effect on Catalyst Efficiency was written by Zhang, Bo;Wang, Hui;Lin, Guo-Qiang;Xu, Ming-Hua. And the article was included in European Journal of Organic Chemistry in 2011.Application of 120121-01-9 This article mentions the following:

The use of unsym. vicinal diamines as ligands for Ru-catalyzed asym. transfer hydrogenation is described. With a SmI₂-mediated cross-coupling protocol, a series of enantiomerically pure unsym. vicinal diamines were readily prepared and examined in the asym. transfer hydrogenation. It was found that an aromatic substituent on the carbon bearing the -NHTs group and a bulky alkyl substituent on the other side, are both very important for the effectiveness of the ligand, suggesting that the substituent has a dramatic effect on the catalyst efficiency. With ligand I, excellent enantioselectivities that are comparable to N-tosyl-1,2-diphenylethane-1,2-diamine (TsDPEN) were achieved. The results provide some helpful information on the mechanism of Ru-catalyzed asym. transfer hydrogenation. In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9Application of 120121-01-9).

(R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9) 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.Application of 120121-01-9

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An iron variant of the Noyori hydrogenation catalyst for the asymmetric transfer hydrogenation of ketones was written by Huo, Shangfei;Wang, Qingwei;Zuo, Weiwei. And the article was included in Dalton Transactions in 2020.COA of Formula: C8H9ClO This article mentions the following:

The design of a new iron catalyst for the asym. transfer hydrogenation of ketones R¹C(O)R² [R¹ = Ph, naphthalen-2-yl, 2,3-dihydro-1H-inden-5-yl, etc.; R² = Me, Et, dimethoxymethyl, (dimethylamino)methyl] was reported. This type of iron catalyst combines the structural characteristics of the Noyori hydrogenation catalyst (an axially chiral 2,2′-bis(phosphino)-1,1′-binaphthyl fragment and the metal-ligand bifunctional motif) and an ene(amido) group SA,RP,SS/SA,RP,RR-I (Ar = Ph, 4-methoxyphenyl) that can activate the iron center. After activation by 8 equiv of potassium tert-butoxide, (SA,RP,SS)-I (Ar = Ph (II)) and (SA,RP,SS)-I (Ar = 4-methoxyphenyl) are active but nonenantioselective catalysts for the transfer hydrogenation of acetophenone and α,β-unsaturated aldehydes R³CHO (R³ = 2,6-dimethylhepta-1,5-dien-1-yl, 2-phenylethenyl) are kept at room temperature in isopropanol. A maximum turnover number of 14480 was observed for (SA,RP,SS) (II) in the reduction of acetophenone. The right combination of the stereochem. of the axially chiral 2,2′-bis(phosphino)-1,1′-binaphthyl group and the carbon-centered chiral amine-imine moiety in (SA,RP,RR)-I (Ar = 4-methoxyphenyl) afforded an enantioselective catalyst for the preparation of chiral alcs. R¹/R³CH(R²/H)OH with moderate to good yields and a broad functional group tolerance. In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9COA of Formula: C8H9ClO).

(R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. Tertiary alcohols cannot be oxidized at all without breaking carbon-carbon bonds, whereas primary alcohols can be oxidized to aldehydes or further oxidized to carboxylic acids.COA of Formula: C8H9ClO

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Efficient asymmetric transfer hydrogenation of ketones in ethanol with chiral iridium complexes of spiroPAP ligands as catalysts was written by Liu, Wei-Peng;Yuan, Ming-Lei;Yang, Xiao-Hui;Li, Ke;Xie, Jian-Hua;Zhou, Qi-Lin. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2015.Related Products of 120121-01-9 This article mentions the following:

Highly efficient iridium catalyzed asym. transfer hydrogenation of simple ketones with ethanol as a hydrogen donor has been developed. By using chiral spiro iridium catalysts, a series of alkyl aryl ketones were hydrogenated to chiral alcs. with up to 98% ee. In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9Related Products of 120121-01-9).

(R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9) belongs to alcohols. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. 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.Related Products of 120121-01-9

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Novel (R)-(+)-limonene-derived ligands: synthesis and application in asymmetric transfer hydrogenations was written by Roszkowski, Piotr;Maurin, Jan K.;Czarnocki, Zbigniew. And the article was included in Tetrahedron: Asymmetry in 2012.Formula: C8H9ClO This article mentions the following:

(R)-(+)-Limonene was transformed into mono-N-tosylated-1,2-diamine derivatives using an N-tosylaziridination procedure followed by sodium azide treatment and reduction on Pd/C. The ligands obtained proved effective in the ruthenium-catalyzed asym. transfer hydrogenation protocol on aromatic ketones. Depending on the ligand and the substrate, the benzylic alc. products were obtained in nearly racemic form or up to 92% ee. In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9Formula: C8H9ClO).

(R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9) 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. Alcohols may be oxidized to give ketones, aldehydes, and carboxylic acids. These functional groups are useful for further reactions. Oxidation of organic compounds generally increases the number of bonds from carbon to oxygen (or another electronegative element, such as a halogen), and it may decrease the number of bonds to hydrogen.Formula: C8H9ClO

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Stereoselective oxidation of racemic 1-arylethanols by basil cultured cells of Ocimum basilicum cv. Purpurascens was written by Itoh, Ken-ichi;Nakamura, Kaoru;Utsukihara, Takamitsu;Sakamaki, Hiroshi;Horiuchi, C. Akira. And the article was included in Biotechnology Letters in 2008.Synthetic Route of C8H9ClO This article mentions the following:

The biotransformation of racemic 1-phenylethanol (30 mg) with plant cultured cells of basil (Ocimum basilicum cv. Purpurascens, 5 g wet wt) by shaking 120 rpm at 25°C for 7 days in the dark gave (R)-(+)-1-phenylethanol and acetophenone in 34 and 24% yields, resp. The biotransformation can be applied to other 1-arylethanols and basil cells oxidized the (S)-alcs. to the corresponding ketones remaining the (R)-alcs. in excellent ee. In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9Synthetic Route of C8H9ClO).

(R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9) 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. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Synthetic Route of C8H9ClO

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Synthesis and Biological Evaluation of Novel 2,4-Diaminoquinazoline Derivatives as SMN2 Promoter Activators for the Potential Treatment of Spinal Muscular Atrophy was written by Thurmond, John;Butchbach, Matthew E. R.;Palomo, Marty;Pease, Brian;Rao, Munagala;Bedell, Louis;Keyvan, Monica;Pai, Grace;Mishra, Rama;Haraldsson, Magnus;Andresson, Thorkell;Bragason, Gisli;Thosteinsdottir, Margret;Bjornsson, Jon Mar;Coovert, Daniel D.;Burghes, Arthur H. M.;Gurney, Mark E.;Singh, Jasbir. And the article was included in Journal of Medicinal Chemistry in 2008.SDS of cas: 120121-01-9 This article mentions the following:

Proximal spinal muscular atrophy (SMA) is an autosomal recessive disorder characterized by death of motor neurons in the spinal cord that is caused by deletion and/or mutation of the survival motor neuron gene (SMN1). Adjacent to SMN1 are a variable number of copies of the SMN2 gene. The two genes essentially differ by a single nucleotide, which causes the majority of the RNA transcripts from SMN2 to lack exon 7. Although both SMN1 and SMN2 encode the same Smn protein amino acid sequence, the loss of SMN1 and incorrect splicing of SMN2 have the consequence that Smn protein levels are insufficient for the survival of motor neurons. The therapeutic goal of our medicinal chem. effort was to identify small-mol. activators of the SMN2 promoter that, by up-regulating gene transcription, would produce greater quantities of full-length Smn protein. Our initial medicinal chem. effort explored a series of C5 substituted benzyl ether based 2,4-diaminoquinazolines that were found to be potent activators of the SMN2 promoter; however, inhibition of DHFR was shown to be an off-target activity that was linked to ATP depletion. A structure-guided approach was used to overcome DHFR inhibition while retaining SMN2 promoter activation. A lead compound, the [(fluorobenzyl)piperidinylmethoxy]quinazolinediamine I, was identified as having high potency and 2.3-fold induction of the SMN2 promoter. I possessed desirable pharmaceutical properties, including excellent brain exposure and long brain half-life following oral dosing to mice. I up-regulated expression of the mouse SMN gene in NSC-34 cells, a mouse motor neuron hybrid cell line. In type 1 SMA patient fibroblasts, I induced Smn in a dose-dependent manner when analyzed by immunoblotting and increased the number of intranuclear particles called gems. The compound restored gems numbers in type I SMA patient fibroblasts to levels near unaffected genetic carriers of SMA. In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9SDS of cas: 120121-01-9).

(R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9) belongs to alcohols. Under appropriate conditions, inorganic acids also react with alcohols to form esters. To form these esters, a wide variety of specialized reagents and conditions can be used. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.SDS of cas: 120121-01-9

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Alcohol – Wikipedia,
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Enantioselective Addition of Dialkylzincs to Aldehydes Catalyzed by (-)-MITH was written by Cheng, Ying-Ni;Wu, Hsyueh-Liang;Wu, Ping-Yu;Shen, Ying-Ying;Uang, Biing-Jiun. And the article was included in Chemistry – An Asian Journal in 2012.Synthetic Route of C8H9ClO This article mentions the following:

An effective catalytic system that imparts high enantioselectivity has been disclosed for the synthesis of optically active alcs., which may undergo further chem. transformations. The enantioselective alkylation of aldehydes with dialkylzincs to afford the corresponding optically active alcs. with excellent enantioselectvities has been achieved in the presence of 0.1-0.5 mol % of the camphor-derived chiral ligand (-)-2-exo-morpholinoisobornane-10-thiol (MITH) at room temperature or at 0°. In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9Synthetic Route of C8H9ClO).

(R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9) belongs to alcohols. Alcohols are weak acids. The most acidic simple alcohols (methanol and ethanol) are about as acidic as water, and most other alcohols are somewhat less acidic. 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.Synthetic Route of C8H9ClO

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Alcohol – Wikipedia,
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Asymmetric transfer hydrogenation of ketones in 2-propanol catalyzed by arsinooxazoline-ruthenium(II) complex was written by Tan, Duan-Ming;Chan, Kin Shing. And the article was included in Tetrahedron Letters in 2005.Quality Control of (R)-1-(3-Chlorophenyl)ethanol This article mentions the following:

Chiral arsinooxazoline Ru(II) complex was an efficient catalyst for asym. transfer hydrogenation of aromatic ketones in 2-propanol. Secondary alcs. with up to 94% enantiomeric excess were obtained at a substrate/catalyst mole ratio of 1000:1. Asym. kinetic resolution was also obtained with 1-arylalkanols at room temperature with 99% ee. In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9Quality Control of (R)-1-(3-Chlorophenyl)ethanol).

(R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. Alcohols may be oxidized to give ketones, aldehydes, and carboxylic acids. These functional groups are useful for further reactions. Oxidation of organic compounds generally increases the number of bonds from carbon to oxygen (or another electronegative element, such as a halogen), and it may decrease the number of bonds to hydrogen.Quality Control of (R)-1-(3-Chlorophenyl)ethanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts