116660-74-3

Basic information

• Product Name: (-)-(3R)-3-hydroxy-1-phenylbutan-1-one
• Synonyms: (-)-(3R)-3-hydroxy-1-phenylbutan-1-one
• CAS NO: 116660-74-3
• Molecular Weight: 164.204
• Mol File: 116660-74-3.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: (-)-(3R)-3-hydroxy-1-phenylbutan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(3R)-3-hydroxy-1-phenylbutan-1-one(116660-74-3)
• EPA Substance Registry System: (-)-(3R)-3-hydroxy-1-phenylbutan-1-one(116660-74-3)

Safety Data

• Hazardous Substances Data: 116660-74-3(Hazardous Substances Data)

Upstream product

• 1144528-41-5 (R)-1-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butan-1-one 
• 495-41-0 1-phenylbut-2-en-1-one 
• 35660-91-4 (E)-1-phenyl-2-buten-1-one 
• 93-89-0 benzoic acid ethyl ester 
• 175650-76-7 (S)-1-(2-Phenyl-[1,3]dioxolan-2-yl)-3-((R)-toluene-4-sulfinyl)-propan-2-ol 
• 175650-75-6 1-(2-Phenyl-[1,3]dioxolan-2-yl)-3-((R)-toluene-4-sulfinyl)-propan-2-one 
• 27773-03-1 ethyl 3,3-(ethylenedioxy)-3-phenylpropanoate 
• 108-05-4 vinyl acetate 
• 13505-39-0 3-hydroxy-1-phenyl-butan-1-one 
• 175650-77-8 (R)-1-(2-Phenyl-[1,3]dioxolan-2-yl)-propan-2-ol 
• 167780-47-4 (R)-2-<1-(2-hydroxypropyl)>-2-phenyl-1,3-dithiane 
• 93-91-4 1-phenylbutan-1,3-dione 

Downstream Products

• 578020-35-6 (2S,4R)-2-phenylpentane-2,4-diol 
• 1286722-86-8 C₂₀H₁₉F₃O₄ 
• 118100-60-0 syn-(1R,3R)-1-phenylbutane-1,3-diol 
• 112420-27-6 anti-(1S,3R)-1-phenylbutane-1,3-diol 

Relevant articles and documents

Chiral Bipyridine Ligand with Flexible Molecular Recognition Site: Development and Application to Copper-Catalyzed Asymmetric Borylation of α,β-Unsaturated Ketones

A novel chiral bipyridine ligand bearing a flexible side chain with a molecular recognition site enables precise stereocontrol through the cooperative action of metal center and hydrogen bonds. This new chiral ligand was applied to the copper-catalyzed as

Regio- and enantioselective reduction of diketones: Preparation of enantiomerically pure hydroxy ketones catalysed by Candida parapsilosis ATCC 7330

Enantiomerically enriched hydroxy ketones were prepared by the reduction of the corresponding diketones with excellent enantiomeric excess (98%) and in good yields (up to 75%) using whole cells of Candida parapsilosis ATCC 7330. Cyclic diketones, such as 1,2-cyclohexanedione and 1,4-cyclohexanedione, resulted in hydroxy ketones as products. Cyclohexane-1,3-dione and 5,5-dimethylcyclohexane-1,3-dione gave dimerised products, such as 2,2′-(ethane-1,1-diyl)bis(3-hydroxycyclohex-2-enone) and 2,2′-(ethane-1,1-diyl)bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) with acetaldehyde generated in situ from whole cells of Candida parapsilosis ATCC 7330, which is reported here for the first time.

Synthesis of new chiral keto alcohols by baker's yeast

Fourteen chiral α- and β-keto alcohols 2a-2r were synthesized by the asymmetric reduction of their corresponding diketones 1a-1r via baker's yeast. In addition, ten corresponding racemic α-keto alcohols were synthesized by the benzoin condensation of their corresponding aldehydes, which were used for the determination of the ee values through their chiral resolution on chiral HPLC. Amongst the 15 diketones, 1j and chiral α-keto alcohols 2i, 2j and chiral β-keto alcohol 2r are novel compounds. Six keto alcohols 2b, 2c, 2d, 2f, 2h and 2p were synthesized by baker's yeast for the first time. There are some studies in the literature where baker's yeast was applied to the diketones 1a, 1g, 1e, 1k and 1n under various conditions different to those reported herein. The yields and the ee values of these studies were not as high as ours. All of the keto alcohols synthesized were characterized by IR, NMR (1H and 13C), and MS. The relationship between the structure of the diketone and the yield, diastereoselectivity and enantiomeric excess is also discussed.