22144-60-1 Usage
Description
(R)-(+)-1-PHENYL-1-BUTANOL, also known as (R)-α-methylbenzyl alcohol, is a chiral secondary alcohol with a phenyl group attached to a chiral carbon atom. It is an enantiomer of (S)-(-)-1-phenyl-1-butanol and exhibits unique properties due to its chiral nature. This organic compound is characterized by its ability to participate in various chemical reactions and is a valuable intermediate in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Uses
Used in Pharmaceutical Industry:
(R)-(+)-1-PHENYL-1-BUTANOL is used as a chiral building block for the synthesis of various pharmaceutical compounds. Its unique stereochemistry allows for the development of enantiomerically pure drugs, which can have significant advantages in terms of efficacy and reduced side effects.
Used in Agrochemical Industry:
In the agrochemical industry, (R)-(+)-1-PHENYL-1-BUTANOL is used as a precursor for the synthesis of chiral pesticides and other agrochemicals. The chiral nature of this compound enables the development of more effective and selective products with reduced environmental impact.
Used in Flavor and Fragrance Industry:
(R)-(+)-1-PHENYL-1-BUTANOL is used as a chiral intermediate in the synthesis of various flavor and fragrance compounds. Its unique smell profile can contribute to the creation of novel and complex scents in perfumes, cosmetics, and other consumer products.
Used in Enantioselective Catalysis:
(R)-(+)-1-PHENYL-1-BUTANOL is used as a substrate in the study of enantioselective catalysis, which is an important area of research in organic chemistry. (R)-(+)-1-PHENYL-1-BUTANOL can be employed to investigate the efficiency and selectivity of various chiral catalysts and enzymes, such as lipase and ketoreductase, in reactions like transesterification and reduction of phenyl alkanones.
Used in Thermodynamic Studies:
(R)-(+)-1-PHENYL-1-BUTANOL is used as a substrate in thermodynamic studies, particularly in the transesterification of phenyl alkanols with butyl acetate in the presence of lipase enzyme. These studies help to understand the factors that influence the equilibrium and kinetics of such reactions, which can be crucial for optimizing industrial processes.
Used in Biocatalytic Reduction:
(R)-(+)-1-PHENYL-1-BUTANOL is also used in the reduction of phenyl alkanones in the presence of ketoreductase enzyme. This biocatalytic process can provide insights into the selectivity and efficiency of enzymatic reduction, which can be applied to the synthesis of chiral alcohols and other valuable compounds.
Check Digit Verification of cas no
The CAS Registry Mumber 22144-60-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,1,4 and 4 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 22144-60:
(7*2)+(6*2)+(5*1)+(4*4)+(3*4)+(2*6)+(1*0)=71
71 % 10 = 1
So 22144-60-1 is a valid CAS Registry Number.
InChI:InChI=1/C10H14O/c1-2-6-10(11)9-7-4-3-5-8-9/h3-5,7-8,10-11H,2,6H2,1H3/t10-/m1/s1
22144-60-1Relevant articles and documents
Manganese catalyzed asymmetric transfer hydrogenation of ketones
Zhang, Guang-Ya,Ruan, Sun-Hong,Li, Yan-Yun,Gao, Jing-Xing
supporting information, p. 1415 - 1418 (2020/11/20)
The asymmetric transfer hydrogenation (ATH) of a wide range of ketones catalyzed by manganese complex as well as chiral PxNy-type ligand under mild conditions was investigated. Using 2-propanol as hydrogen source, various ketones could be enantioselectively hydrogenated by combining cheap, readily available [MnBr(CO)5] with chiral, 22-membered macrocyclic ligand (R,R,R',R')-CyP2N4 (L5) with 2 mol% of catalyst loading, affording highly valuable chiral alcohols with up to 95% ee.
Cobalt-catalyzed asymmetric hydrogenation of ketones: A remarkable additive effect on enantioselectivity
Du, Tian,Wang, Biwen,Wang, Chao,Xiao, Jianliang,Tang, Weijun
supporting information, p. 1241 - 1244 (2020/10/02)
A chiral cobalt pincer complex, when combined with an achiral electron-rich mono-phosphine ligand, catalyzes efficient asymmetric hydrogenation of a wide range of aryl ketones, affording chiral alcohols with high yields and moderate to excellent enantioselectivities (29 examples, up to 93% ee). Notably, the achiral mono-phosphine ligand shows a remarkable effect on the enantioselectivity of the reaction.
A relay catalysis strategy for enantioselective nickel-catalyzed migratory hydroarylation forming chiral α-aryl alkylboronates
Chen, Jian,Liang, Yong,Ma, Jiawei,Meng, Lingpu,Zhang, Yao,Zhu, Shaolin
supporting information, p. 3171 - 3188 (2021/11/16)
Ligand-controlled reactivity plays an important role in transition-metal catalysis, enabling a vast number of efficient transformations to be discovered and developed. However, a single ligand is generally used to promote all steps of the catalytic cycle (e.g., oxidative addition, reductive elimination), a requirement that makes ligand design challenging and limits its generality, especially in relay asymmetric transformations. We hypothesized that multiple ligands with a metal center might be used to sequentially promote multiple catalytic steps, thereby combining complementary catalytic reactivities through a simple combination of simple ligands. With this relay catalysis strategy (L/L?), we report here the first highly regio- and enantioselective remote hydroarylation process. By synergistic combination of a known chain-walking ligand and a simple asymmetric cross-coupling ligand with the nickel catalyst, enantioenriched α-aryl alkylboronates could be rapidly obtained as versatile synthetic intermediates through this formal asymmetric remote C(sp3)-H arylation process.
