Category: 120121-01-9

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. 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

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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. 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

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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掳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鈥昈鈭?. 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

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

The Manganese(I)-Catalyzed Asymmetric Transfer Hydrogenation of Ketones: Disclosing the Macrocylic Privilege was written by Passera, Alessandro;Mezzetti, Antonio. And the article was included in Angewandte Chemie, International Edition in 2020.SDS of cas: 120121-01-9 This article mentions the following:

The bis(carbonyl) manganese(I) complex [Mn(CO)₂(ligand)]Br with a chiral (NH)₂P₂ macrocyclic ligand catalyzes the asym. transfer hydrogenation of polar double bonds with 2-propanol as the hydrogen source. Ketones (43 substrates) are reduced to alcs. in high yields (up to >99%) and with excellent enantioselectivities (90-99% ee). A stereochem. model based on attractive CH-π interactions is proposed. 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. 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. 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.SDS of cas: 120121-01-9

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Efficient asymmetric synthesis of chiral alcohols using high 2-propanol tolerance alcohol dehydrogenase SmADH2 via an environmentally friendly TBCR system was written by Yang, Zeyu;Fu, Hengwei;Ye, Wenjie;Xie, Youyu;Liu, Qinghai;Wang, Hualei;Wei, Dongzhi. And the article was included in Catalysis Science & Technology in 2020.Quality Control of (R)-1-(3-Chlorophenyl)ethanol This article mentions the following:

Alc. dehydrogenases (ADHs) together with the economical substrate-coupled cofactor regeneration system play a pivotal role in the asym. synthesis of chiral alcs.; however, severe challenges concerning the poor tolerance of enzymes to 2-propanol and the adverse effects of the byproduct, acetone, limit its applications, causing this strategy to lapse. Herein, a novel ADH gene smadh2 was identified from Stenotrophomonas maltophilia by traditional genome mining technol. The gene was cloned into Escherichia coli cells and then expressed to yield SmADH2. SmADH2 has a broad substrate spectrum and exhibits excellent tolerance and superb activity to 2-propanol even at 10.5 M (80%, volume/volume) concentration Moreover, a new thermostatic bubble column reactor (TBCR) system is successfully designed to alleviate the inhibition of the byproduct acetone by gas flow and continuously supplement 2-propanol. The organic waste can be simultaneously recovered for the purpose of green synthesis. In the sustainable system, structurally diverse chiral alcs. are synthesized at a high substrate loading (>150 g L^-1) without adding external coenzymes. Among these, about 780 g L^-1 (6 M) Et acetoacetate is completely converted into Et (R)-3-hydroxybutyrate in only 2.5 h with 99.9% ee and 7488 g L^-1 d^-1 space-time yield. Mol. dynamics simulation results shed light on the high catalytic activity toward the substrate. Therefore, the high 2-propanol tolerance SmADH2 with the TBCR system proves to be a potent biocatalytic strategy for the synthesis of chiral alcs. on an industrial scale. 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. 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.Quality Control of (R)-1-(3-Chlorophenyl)ethanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Dioxygenase-catalysed oxidation of disubstituted benzene substrates: benzylic monohydroxylation versus aryl cis-dihydroxylation and the meta effect was written by Boyd, Derek R.;Sharma, Narain D.;Bowers, Nigel I.;Dalton, Howard;Garrett, Mark D.;Harrison, John S.;Sheldrake, Gary N.. And the article was included in Organic & Biomolecular Chemistry in 2006.Recommanded Product: (R)-1-(3-Chlorophenyl)ethanol This article mentions the following:

Biotransformations of a series of ortho-, meta- and para-substituted ethylbenzene and propylbenzene substrates have been carried out, using Pseudomonas putida UV4, a source of toluene dioxygenase (TDO). The ortho- and para-substituted alkylbenzene substrates yielded, exclusively, the corresponding enantiopure cis-dihydrodiols of the same absolute configuration. However, the meta isomers, generally, gave benzylic alc. bioproducts, in addition to the cis-dihydrodiols (the meta effect). The benzylic alcs. were of identical (R) absolute configuration but enantiomeric excess values were variable. The similar (2R) absolute configurations of the cis-dihydrodiols are consistent with both the Et and Pr groups having dominant stereodirecting effects over the other substituents. The model used earlier, to predict the regio- and stereo-chem. of cis-dihydrodiol bioproducts derived from substituted benzene substrates has been refined, to take account of non-sym. substituents like Et or Pr groups. The formation of benzylic hydroxylation products, from meta-substituted benzene substrates, without further cis-dihydroxylation to yield triols provides a further example of the meta effect during toluene dioxygenase-catalyzed oxidations In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9Recommanded Product: (R)-1-(3-Chlorophenyl)ethanol).

(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. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Recommanded Product: (R)-1-(3-Chlorophenyl)ethanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Influence of amino acid moiety accessibility on the chiral recognition of cyclodextrin-amino acid mixed selectors in enantioselective gas chromatography was written by Stephany, Olivier;Tisse, Severine;Coadou, Gael;Bouillon, Jean-Philippe;Peulon-Agasse, Valerie;Cardinael, Pascal. And the article was included in Journal of Chromatography A in 2012.Recommanded Product: (R)-1-(3-Chlorophenyl)ethanol This article mentions the following:

Original mixed selectors were synthesized by coupling a single L-valine diamide moiety on permethylated β-cyclodextrin. The structures of the new selectors were designed to limit the interactions between the L-valine derivative and cyclodextrin by removing the amino acid moiety from the cyclodextrin cavity by an amide linkage on mono-6-amino permethylated β-CD or the insertion of a carboxymethyl group. The accessibility of the amino acid group moiety was thus facilitated. The new mixed selectors exhibited better enantioselectivity than Chirasil-L-Val for half (selector based on mono-6-amino permethylated β-CD) or more (selector with the carboxymethyl group) of the 41 amino acid derivatives Mol. modeling confirmed that these results could be attributed to an increase in the distance between the chiral center of the amino acid and the cyclodextrin cavity allowing better access of the amino acid moiety. These new mixed chiral selectors demonstrated a novel enantioselective capability with the successful separation of >90 racemic mixtures among the 105 chiral compounds tested. These mixed selectors exhibited enhanced enantioselectivity in comparison to binary selectors previously described with respect to both enantiomer resolution and the number of separated chiral compounds Also, an improvement of the enantioseparation factors compared to the corresponding parent phases for the amino acid derivatives was observed in many cases. These mixed selectors should therefore be considered some of the most versatile selectors for chiral gas chromatog. In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9Recommanded Product: (R)-1-(3-Chlorophenyl)ethanol).

(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. 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.Recommanded Product: (R)-1-(3-Chlorophenyl)ethanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

3,3′-Diphosphoryl-1,1′-bi-2-naphthol-Zn(II) Complexes as Conjugate Acid-Base Catalysts for Enantioselective Dialkylzinc Addition to Aldehydes was written by Hatano, Manabu;Miyamoto, Takashi;Ishihara, Kazuaki. And the article was included in Journal of Organic Chemistry in 2006.Recommanded Product: (R)-1-(3-Chlorophenyl)ethanol This article mentions the following:

A highly enantioselective dialkylzinc (R²₂Zn) addition to a series of aromatic, aliphatic, and heteroaromatic aldehydes was developed based on conjugate Lewis acid-Lewis base catalysis. Bifunctional BINOL ligands bearing phosphine oxides [P(:O)R₂], phosphonates [P(:O)(OR)₂], or phosphoramides [P(:O)(NR₂)₂] at the 3,3′-positions were prepared by using a phospho-Fries rearrangement as a key step. The coordination of a NaphO-Zn(II)-R² center as a Lewis acid to a carbonyl group in a substrate and the activation of R²₂Zn(II) with a phosphoryl group (P:O) as a Lewis base in the 3,3′-diphosphoryl-BINOL-Zn(II) catalyst could promote carbon-carbon bond formation with high enantioselectivities (up to >99% ee). Mechanistic studies were performed by X-ray analyses of a free ligand and a tetranuclear Zn(II) cluster, a ³¹P NMR experiment on Zn(II) complexes, an absence of nonlinear effect between the ligand and Et-adduct of benzaldehyde, and stoichiometric reactions with some chiral or achiral Zn(II) complexes to propose a transition-state assembly including monomeric active intermediates. In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9Recommanded Product: (R)-1-(3-Chlorophenyl)ethanol).

(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. 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.Recommanded Product: (R)-1-(3-Chlorophenyl)ethanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts