143394-10-9

Basic information

• Product Name: (S,S)-α,α'-dimethyl-1,4-benzenedimethanol
• Synonyms: (S,S)-α,α'-dimethyl-1,4-benzenedimethanol
• CAS NO: 143394-10-9
• Molecular Weight: 166.22
• Mol File: 143394-10-9.mol

Chemical Properties

• CAS DataBase Reference: (S,S)-α,α'-dimethyl-1,4-benzenedimethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (S,S)-α,α'-dimethyl-1,4-benzenedimethanol(143394-10-9)
• EPA Substance Registry System: (S,S)-α,α'-dimethyl-1,4-benzenedimethanol(143394-10-9)

Safety Data

• Hazardous Substances Data: 143394-10-9(Hazardous Substances Data)

Upstream product

• 105-05-5 1,4-diethylbenzene 
• 1009-61-6 1,4-Diacetylbenzene 
• 935-14-8 1,4-diethynylbenzene 
• 101219-72-1 (S)-1-(4-ethylphenyl)ethan-1-ol 
• 627-93-0 hexanedioic acid dimethyl ester 
• 6781-43-7 1,4-bis(1-hydroxyethyl)benzene 
• 108-22-5 Isopropenyl acetate 
• 912334-66-8 C₁₈H₂₆O₄ 
• 143329-80-0 (R,R)-α,α'-dimethyl-1,4-benzenedimethanol diacetate 
• 108124-68-1 α,α'-dimethyl-1,4-benzenedimethanol diacetate 

Relevant articles and documents

Chiral polyesters by dynamic kinetic resolution polymerization

(Figure Presented) Problem resolved: Enzymatic polymerization was combined with an in situ Rucatalyzed racemization process. The reaction mixture comprises a racemic mixture of a chiral diol and dimethyl adipate. Because of the high stereoselectivity of the enzyme Candida antarctica lipase B (CALB), the S-configured stereocenters of the chiral diol are practically nonreactive. Polycondensation was achieved by concurrent racemization of the S- into the R-configured centers.

Multi-substituted chiral (1 - hydroxyethyl) benzene and asymmetric synthesis method thereof

The invention relates to polysubstituted chiral (1-ethoxy)benzene. The specific structure of the polysubstituted chiral (1-ethoxy)benzene is as shown in a formula II. The invention also discloses a 'two-step one-pot' synthetic method of the polysubstituted chiral (1-ethoxy)benzene. The 'two-step one-pot' synthetic method is characterized by taking polyacetylenyl substituted benzene (I) as a raw material, and comprises the following steps: step (1) taking fluorine-containing alcohol and water as solvents, carrying out hydration reaction under the catalysis of trifluoromethanesulfonic acid, thusgenerating an intermediate-ketone; step (2) directly adding a complex of mono-sulfonyl chiral diamine and metal ruthenium, rhodium or iridium as a catalyst in a reaction system, adding alkali, supplementing hydrogen, and carrying out asymmetric hydrogenation reaction, thus obtaining a product II; or directly adding the complex of the mono-sulfonyl chiral diamine and the metal ruthenium, rhodium or iridium as the catalyst in the reaction system, using a mixture of sodium formate or formic acid and triethylamine as a hydrogen source, and carrying out the asymmetric transfer hydrogenation reaction, thus obtaining the product II. According to the 'two-step one-pot' synthetic method disclosed by the invention, the operation is simple, the raw material is easy to obtain, and enantioselectivityand diastereoselectivity are very high. (The formula II is shown in the description).

One-pot synthesis of chiral alcohols from alkynes by CF3SO3H/ruthenium tandem catalysis

A practical one-pot synthesis of chiral alcohols from readily available alkynes via tandem catalysis by the combination of CF3SO3H and a fluorinated chiral diamine Ru(ii) complex in aqueous CF3CH2OH is described. Very interestingly, the combination of fluorinated catalysts and solvent exhibits a positive fluorine effect on the reactivity and enantioselectivity. A range of chiral alcohols with wide functional group tolerance was obtained in high yield and excellent stereoselectivity under simple and mild conditions.

Transformation of Alkynes into Chiral Alcohols via TfOH-Catalyzed Hydration and Ru-Catalyzed Tandem Asymmetric Hydrogenation

A novel full atom-economic process for the transformation of alkynes into chiral alcohols by TfOH-catalyzed hydration coupled with Ru-catalyzed tandem asymmetric hydrogenation in TFE under simple conditions has been developed. A range of chiral alcohols was obtained with broad functional group tolerance, good yields, and excellent stereoselectivities.

Mechanistic basis for the enantioselectivity of the anaerobic hydroxylation of alkylaromatic compounds by ethylbenzene dehydrogenase

The enantioselectivity of reactions catalyzed by ethylbenzene dehydrogenase, a molybdenum enzyme that catalyzes the oxygen-independent hydroxylation of many alkylaromatic and alkylheterocyclic compounds to secondary alcohols, was studied by chiral chromatography and theoretical modeling. Chromatographic analyses of 22 substrates revealed that this enzyme exhibits remarkably high reaction enantioselectivity toward (S)-secondary alcohols (18 substrates converted with > 99% ee). Theoretical QM:MM modeling was used to elucidate the structure of the catalytically active form of the enzyme and to study the reaction mechanism and factors determining its high degree of enantioselectivity. This analysis showed that the enzyme imposes strong stereoselectivity on the reaction by discriminating the hydrogen atom abstracted from the substrate. Activation of the pro(S) hydrogen atom was calculated to be 500 times faster than of the pro(R) hydrogen atom. The actual hydroxylation step (i.e., hydroxyl group rebound reaction to a carbocation intermediate) does not appear to be enantioselective enough to explain the experimental data (the calculated rate ratios were in the range of only 2-50 for pro(S): pro(R)-oriented OH rebound).

Advantageous asymmetric ketone reduction with a competitive hydrogenation/transfer hydrogenation system using chiral bifunctional iridium catalysts

Hydrogenation of aromatic ketones with chiral bifunctional amidoiridium complexes proceeds in preference to transfer hydrogenation in methanol, in which the pressurised hydrogen can suppress unintended racemisation of the alcoholic product, leading to enh

Varying the ratio of formic acid to triethylamine impacts on asymmetric transfer hydrogenation of ketones

Asymmetric transfer hydrogenation (ATH) is frequently carried out in the azeotropic mixture of formic acid (F) and triethylamine (T), where the F/T molar ratio is 2.5. This study shows that the F/T ratio affects both the reduction rate and enantioselectivity, with the optimum ratio being 0.2 in the ATH of ketones with the Ru-TsDPEN catalyst. Under such conditions, a range of substrates have been reduced, affording high yields and good to excellent enantioselectivities. In comparison with the common azeotropic F-T system, the reduction is faster. This protocol improves both the classic azeotropic and the aqueous-formate system when using water-insoluble ketones.

Asymmetric synthesis of chiral tectons with tetrapodal symmetry: Fourfold asymmetric reactions

The diastereoselective fourfold addition to Ellman-type imines furnished after deprotection the tetrapodal amines in excellent yields. The unprecedented asymmetric fourfold addition of hydride and alkylzinc reagents to tetrapodal ketones and aldehydes, respectively, is achieved by employing CBS-reduction or [2.2]paracyclophane-based ketimine ligands with good to excellent global enantiomeric ratios.

Process for the preparation of an optically active ester

The invention relates to a process for the preparation of an optically active compound from raw materials comprising a di-ester and a chiral hydroxy-compound according to formula (I): wherein: - R1, R2, R4 and R5/sub

Combined ruthenium(II) and lipase catalysis for efficient dynamic kinetic resolution of secondary alcohols. Insight into the racemization mechanism

Pentaphenylcyclopentadienyl ruthenium complexes (3) are excellent catalysts for the racemization of secondary alcohols at ambient temperature. The combination of this process with enzymatic resolution of the alcohols results in a highly efficient synthesis of enantiomerically pure acetates at room temperature with short reaction times for most substrates. This new reaction was applied to a wide range of functionalized alcohols including heteroaromatic alcohols, and for many of the latter, enantiopure acetates were efficiently prepared for the first time via dynamic kinetic resolution (DKR). Different substituted cyclopentadienyl ruthenium complexes were prepared and studied as catalysts for racemization of alcohols. Pentaaryl-substituted cyclopentadienyl complexes were found to be highly efficient catalysts for the racemization. Substitution of one of the aryl groups by an alkyl group considerably slows down the racemization process. A study of the racemization of (S)-1-phenylethanol catalyzed by ruthenium hydride η5-Ph5CpRu(CO) 2H (8) indicates that the racemization takes place within the coordination sphere of the ruthenium catalyst. This conclusion was supported by the lack of ketone exchange in the racemization of (S)-1-phenylethanol performed in the presence of p-tolyl methyl ketone (1 equiv), which gave 1% of 1-(p-tolyl)ethanol. The structures of ruthenium chloride and iodide complexes 3a and 3c and of ruthenium hydride complex 8 were confirmed by X-ray analysis.