22135-49-5

Usage

Purification Methods

Purify the alcohol by distillation, and the distllate crystallises on cooling. The hydrochloride has [] 20 +45.1o (c 4.8, *C6H6). The (-)-hydroperoxide has b58o/0.005mm, n D 1.5123,  D -2.14o, (l = 0.5dcm, neat). [Holding & Ross J Chem Soc 145 1954, Davies & Feld J Chem Soc 4637 1958.] The (±)-racemate has b 73o/0.05mm, and its 4-nitrophenylhydrazone has m 58o. [Beilstein 6 IV 3272.]

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-/m0/s1

Upstream product

• 86561-24-2 (RS)-1-phenyl-1-butanol acetate 
• 123-72-8 butyraldehyde 
• 123463-22-9 (S)-1-{[Dimethyl-((S)-1-phenyl-butyl)-silanyl]-methyl}-2-methoxymethyl-pyrrolidine 
• 495-40-9 propiophenone 
• 614-14-2 1-Phenyl-1-butanol 
• 108-05-4 vinyl acetate 
• 5876-76-6 (R)-4-phenylbut-3-yn-2-ol 
• 1817-57-8 4-phenyl-3-butyne-2-one 
• 3262-89-3 triphenylboroxine 
• 2234-82-4 1-propylmagnesium chloride 
• 100-52-7 benzaldehyde 
• 64-17-5 ethanol 
• 98-86-2 acetophenone 
• 622-76-4 1-phenyl-1-butyne 

Downstream Products

• 4352-42-5 (S)-1-cyclohexyl-1-butanol 
• 58687-89-1 (S)-1-phenyl-butyl hydroperoxide 
• 40628-81-7 (S)-1-acetoxy-1-phenylbutane 
• 156725-12-1 (S)-1-phenylbutyl vinyl ether 
• 71-36-3 butan-1-ol 
• 197709-54-9 (R)-(+)-N-(1-phenylbutoxy)phthalimide 
• 1073536-00-1 C₁₇H₁₆N₂O₆ 

Relevant academic research and scientific papers

New chiral lithium aluminum hydrides based on biphenyl-2,2′- bisfenchol (BIFOL): Structural analyses and enantioselective reductions of aryl alkyl ketones

A series of new chiral lithium aluminum hydrides based on BIFOL (biphenyl-2,2′-bisfenchol) and various alkyl alcohols (i.e., methanol, n-butanol, tert-butanol yielding BIFAl-H's) was synthesized and characterized by single crystal X-ray analyses. These investigations point to alkoxide redistribution for BIFAl-H-(O-tBu) (biphenyl-2,2′-bisfenchol aluminum hydride) species. The new BIFAl-H reagents are suitable to reduce aryl alkyl ketones with up to 62% ee. Computational transition structure analyses help to explain the experimentally observed enantioselectivities.

Diisopinocampheylchloroborane, a Remarkably Efficient Chiral Reducing Agent for Aromatic Prochiral Ketones

Diisopinocampheylchloroborane, readily prepared in high chemical and optical purities (99percent ee) from (+)-α-pinene (92percent ee) via hydroboration, followed by treatment with dry hydrogen chloride in ether, reduces ketones at convenient rates at -25

Enantioselective reduction of aryl ketones using LiBH4 and TarB-X: A chiral Lewis acid

High enantioselectivities are obtained using a tartaric acid-derived boronate ester in combination with lithium borohydride for asymmetric reduction of aryl ketones. The chiral Lewis acid, TarB-X, is easily prepared in 1 h, and the resulting alcohols are

Cinchona-Alkaloid-Derived NNP Ligand for Iridium-Catalyzed Asymmetric Hydrogenation of Ketones

Most ligands applied for asymmetric hydrogenation are synthesized via multistep reactions with expensive chemical reagents. Herein, a series of novel and easily accessed cinchona-alkaloid-based NNP ligands have been developed in two steps. By combining [Ir(COD)Cl]2, 39 ketones including aromatic, heteroaryl, and alkyl ketones have been hydrogenated, all affording valuable chiral alcohols with 96.0-99.9% ee. A plausible reaction mechanism was discussed by NMR, HRMS, and DFT, and an activating model involving trihydride was verified.

Manganese catalyzed asymmetric transfer hydrogenation of ketones

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.

Ruthenium-catalyzed hydrogenation of aromatic ketones using chiral diamine and monodentate achiral phosphine ligands

The Ru-catalyzed asymmetric hydrogenation of ketones with chiral diamine and monodentate achiral phosphine has been developed. A wide range of ketones were hydrogenated to afford the corresponding chiral secondary alcohols in good to excellent enantioselectivities (up to 98.1% ee). In addition, an appropriate mechanism for the asymmetric hydrogenation was proposed and verified by NMR spectroscopy.

An Enantioconvergent Benzylic Hydroxylation Using a Chiral Aryl Iodide in a Dual Activation Mode

The application of a triazole-substituted chiral iodoarene in a direct enantioselective hydroxylation of alkyl arenes is reported. This method allows the rapid synthesis of chiral benzyl alcohols in high yields and stereocontrol, despite its nontemplated nature. In a cascade activation consisting of an initial irradiation-induced radical C-H-bromination and a consecutive enantioconvergent hydroxylation, the iodoarene catalyst has a dual role. It initiates the radical bromination in its oxidized state through an in-situ-formed bromoiodane and in the second, Cu-catalyzed step, it acts as a chiral ligand. This work demonstrates the ability of a chiral aryl iodide catalyst acting both as an oxidant and as a chiral ligand in a highly enantioselective C-H-activating transformation. Furthermore, this concept presents an enantioconvergent hydroxylation with high selectivity using a synthetic catalyst.

P-chirogenic Trost ligands mediated asymmetric hydrogenation of simple ketones

Herein, we report a highly active catalyst system consisting of (Rc,Rc,Rp,Rp)-P-chirogenic Trost ligand and [Ru(C6H6)Cl2]2 for asymmetric hydrogenation of simple ketones, affording the corresponding optically active alcohols in moderate enantioselectivity. A synergetic effect between P- and C-chirogenic centers of the P-chirogenic Trost ligands was observed in this asymmetric hydrogenation process.

Chiral amino-pyridine-phosphine tridentate ligand, manganese complex, and preparation method and application thereof

The invention discloses a chiral amino-pyridine-phosphine tridentate ligand, a manganese complex, and a preparation method and application thereof. The chiral amino-pyridine-phosphine tridentate ligand is shown as a formula II, and the manganese complex of the chiral amino-pyridine-phosphine tridentate ligand can be used for efficiently catalyzing and hydrogenating ketone compounds to prepare chiral alcohol compounds in a high enantioselectivity mode. The chiral amino-pyridine-phosphine tridentate ligand and the manganese complex are simple in synthesis process, good in stability, high in catalytic activity and mild in reaction conditions.

Manganese-Catalyzed Enantioselective Hydrogenation of Simple Ketones Using an Imidazole-Based Chiral PNN Tridentate Ligand

A series of Mn(I) catalysts containing imidazole-based chiral PNN tridentate ligands with controllable 'side arm' groups have been established, enabling the inexpensive base-promoted asymmetric hydrogenation of simple ketones with outstanding activities (up to 8200 TON) and good enantioselectivities (up to 88.5percent ee). This protocol features wide substrate scope and functional group tolerance, thereby providing easy access to a key intermediate of crizotinib.