105836-17-7

Basic information

• Product Name: (R)-1-phenyl-3-pentanol
• Synonyms: (R)-1-phenyl-3-pentanol
• CAS NO: 105836-17-7
• Molecular Weight: 164.247
• Mol File: 105836-17-7.mol
• Article Data: 116

Chemical Properties

• CAS DataBase Reference: (R)-1-phenyl-3-pentanol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-phenyl-3-pentanol(105836-17-7)
• EPA Substance Registry System: (R)-1-phenyl-3-pentanol(105836-17-7)

Safety Data

• Hazardous Substances Data: 105836-17-7(Hazardous Substances Data)

Upstream product

• 538-68-1 pentylbenzene 
• 104-53-0 3-phenyl-propionaldehyde 
• 2386-64-3 ethylmagnesium chloride 
• 1313022-82-0 (R)-(3-(benzyloxy)pent-4-en-1-yl)benzene 
• 40339-21-7 penta-3,4-dienyl-benzene 
• 1352127-75-3 4,4,5,5-tetramethyl-2-(1-phenylpentan-3-yl)-1,3,2-dioxaborolane 
• 557-20-0 diethylzinc 
• 125303-62-0 Toluene-4-sulfonic acid (S)-3-hydroxy-5-phenyl-pentyl ester 
• 27975-78-6 1-phenyl-1-pentyn-3-ol 
• 110611-22-8 (1E,3R)-1-phenylpent-1-en-3-ol 
• 1589-82-8 phenylmagnesium bromide 
• 75-16-1 methylmagnesium bromide 
• 913258-22-7 (S)-1,2-epoxy-4-phenylbutane 
• 959685-47-3 (R)-4,4,5,5-tetramethyl-2-(1-phenylpentan-3-yl)-1,3,2-dioxaborolane 

Downstream Products

• 1416148-62-3 (R)-3-mesyloxy-1-phenylpentane 
• 1745-16-0 5-phenylpent-2-ene 
• 1416148-64-5 (S)-3-mesyloxy-1-phenylpentane 
• 1053655-39-2 (3R,4R,5S)-4-Acetylamino-5-azido-3-((R)-1-ethyl-3-phenyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester 
• 78571-82-1 (R)-α-ethylbenzenepropanol acetate 

Relevant articles and documents

Polymer-supported chiral α-amino amides for the asymmetric addition of diethylzinc to aldehydes: Transforming an inactive homogeneous system into an efficient catalyst

A series of polymer-supported α-amino amides derived from natural amino acids have been easily synthesized and fully characterized. Their chiral Zn (II) complexes catalyzed the enantioselective addition of diethylzinc to aldehydes to form chiral secondary alcohols in high yields and enantioselectivities up to 95% were obtained. The results showed that the immobilization of this chiral ligand onto a polymeric matrix transforms the inactive homogeneous system into an efficient catalyst. Moreover, the supported catalyst could be re-used at least five times without any significant loss of catalytic activity.

Rhodium-Catalyzed Enantioselective Intermolecular Hydroalkoxylation of Allenes and Alkynes with Alcohols: Synthesis of Branched Allylic Ethers

Regio- and enantioselective additions of alcohols to either terminal allenes or internal alkynes provides access to allylic ethers by using a RhI/diphenyl phosphate catalytic system. This method provides an atom-economic way to obtain chiral aliphatic and aryl allylic ethers in moderate to good yield with good to excellent enantioselectivities.

Enantioselective addition of diethylzinc to aldehydes catalyzed by a new chiral β-amino alcohol derived from D-mannitol

A new chiral β-dialkylamino alcohol 1 prepared from D-mannitol has been used as a highly effective chiral catalyst for the enantioselective addition of diethylzinc to unhindered aliphatic aldehydes to afford the product alcohols in up to 94% ee.

Catalytic enantioselective reactions. Part 18: Preparation of 3-deoxy-3-N,N-dialkylamino-1,2;5,6-di-O-isopropylidene-D-altritol derivatives from D-mannitol and their applications for catalytic enantioselective addition of dialkylzinc to aldehydes

A series of new chiral β-aminoalcohols, 3-deoxy-3-N,N-dialkylamino-1,2;5,6-di-O-isopropylidene-D-altritol derivatives 2-4 possessing a variety of amine substituents at the 3-position and thiol or acetylthio group at the 4-position was prepared from D-mannitol and enantioselective additions of diethylzinc to aldehydes using them as chiral catalysts were examined. Copyright (C) 2000 Elsevier Science Ltd.

Catalysis by amino acid-derived tetracoordinate complexes: Enantioselective addition of dialkylzincs to aliphatic and aromatic aldehydes

Me2Zn and Et2Zn added to aromatic and aliphatic aldehydes in the presence of 3 mol % of 2. (S)-1-Phenylethanol (91% ee) and (S)-1-phenylpropanol (86% ee) were synthesized from benzaldehyde and (S)-1-furan-2-yl-1-propanol (86% ee) from 2-furaldehyde. Nonanal and 3-phenylpropanal provided (S)-3-undecanol (96% ee) and (S)-1-phenyl-3-pentanol (94% ee). A solid-phase variant was effective with reduced ee's (e.g., 86% ee → 79% ee) for (S)-1-phenylpropanol.

ENANTIOSELECTIVE ETHYLATION OF ALDEHYDES CATALYZED BY CHIRAL C2-SYMMETRICAL β-HYDROXY-m-XYLYLENE DIAMINES

Optically active C2-symmetric aminoalcohols derived from m-xylylene diamine act as catalysts in enantioselective alkylation of aromatic and aliphatic aldehydes with diethylzinc.The chemical yields are good, and the enantiomeric excesses vary fr

Stereospecific Nickel-Catalyzed Reductive Cross-Coupling of Alkyl Tosylate and Allyl Alcohol Electrophiles

The stereospecific cross-coupling of easily accessed electrophiles holds significant promise in the construction of C-C bonds. Herein, we report a nickel-catalyzed reductive coupling of allyl alcohols with chiral, nonracemic alkyl tosylates. This cross-coupling delivers valuable allylation products with high levels of stereospecificity across a range of substrates. The catalytic system consists of a simple nickel salt in conjunction with a commercially available reductant and importantly represents a rare example of a cross-coupling involving the C-O bonds of two electrophiles.

Enantioselective addition of diethylzinc to aldehydes catalyzed by 5-cis-substituted proline derivatives

5-Cis-substituted prolinols, prolinamines, and prolinamine sulfonamides proved to be efficient ligands for the enantioselective addition of diethylzinc to aldehydes, providing up to 99% ee. The sense of asymmetric induction can be controlled by the nature

Cobalt-Catalyzed Aminocarbonylation of Alkyl Tosylates: Stereospecific Synthesis of Amides

Metal-catalyzed aminocarbonylation is a standard approach for installing amide functionality in chemical synthesis. Despite broad application of this transformation using aryl or vinyl electrophiles, there are few examples involving unactivated aliphatic substrates. Furthermore, there are no stereocontrolled aminocarbonylations of alkyl electrophiles known. Herein, we report a stereospecific aminocarbonylation of unactivated alkyl tosylates for the synthesis of enantioenriched amides. This cobalt-catalyzed transformation uses a remarkably broad range of amines and proceeds with excellent stereospecificity and chemoselectivity.