103668-44-6

Basic information

• Product Name: (1SR,1RS)-1-phenyl-4-methylpentane-1,3-diol
• Synonyms: (1SR,1RS)-1-phenyl-4-methylpentane-1,3-diol
• CAS NO: 103668-44-6
• Molecular Weight: 194.274
• Mol File: 103668-44-6.mol

Chemical Properties

• CAS DataBase Reference: (1SR,1RS)-1-phenyl-4-methylpentane-1,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (1SR,1RS)-1-phenyl-4-methylpentane-1,3-diol(103668-44-6)
• EPA Substance Registry System: (1SR,1RS)-1-phenyl-4-methylpentane-1,3-diol(103668-44-6)

Safety Data

• Hazardous Substances Data: 103668-44-6(Hazardous Substances Data)

Upstream product

• 115827-02-6 3-hydroxy-4-methyl-1-phenylpentan-1-one 
• 59357-09-4 (+/-)-1-hydroxy-4-methyl-1-phenyl-3-pentanone 
• 132157-37-0 4-Methyl-1-phenyl-3-(trimethylsilyloxy)-1-pentanol 
• 116212-29-4 2-{4-methyl-1-phenyl-3-(trimethylsilyloxy)pentyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 27644-03-7 4-methyl-1-phenyl-pent-3-en-1-ol 
• 100-46-9 benzylamine 
• 43108-74-3 3-hydroxy-3-methyl-1-phenyl-1-butanone 
• 78-84-2 isobutyraldehyde 
• 98-86-2 acetophenone 
• 142321-70-8 1,1-Dibromo-4-methyl-3-pentanol 
• 132157-15-4 5,5-Dibromo-2-methyl-2-pentene 
• 132047-52-0 1,1-Dibromo-4-methyl-3-(trimethylsilyloxy)pentane 
• 870-63-3 prenyl bromide 
• 100-52-7 benzaldehyde 

Relevant articles and documents

Diastereoselective reduction of β-hydroxyketones with amineboranes in the presence of lithium perchlorate

The reduction of β-hydroxyketones with amineboranes in the presence of lithium perchlorate produces the corresponding anti 1,3-diols as major products.

Simple metal alkoxides as effective catalysts for the hetero-aldol-Tishchenko reaction

(equation presented) This paper reports the utility of simple metal alkoxides for the catalytic, stereoselective hetero-aldol-Tishchenko reaction (eq 1). Choice of metal alkoxide is crucial to achieving high efficiency and stereoselectivity. Whereas NaO-t

Stereoselective catalytic Tishchenko reduction of β-hydroxyketones using scandium triflate

A number of aliphatic and aromatic β-hydroxyketones were reduced to 1,3-diol monoesters by aldehydes in the presence of a catalytic amount of scandium triflate. Chiral substrates were reduced with high 1,3-anti diastereoselectivity.

The zirconium alkoxide-catalyzed aldol-tishchenko reaction of ketone aldols

The aldol-Tishchenko reaction of ketone aldols as enol equivalents has been developed as an efficient strategy to furnish differentiated 1,3-anti-diol monoesters in one step. The thermodynamically unstable ketone aldols undergo a facile retro-aldolization to yield a presumed zirconium enolate in situ, which then undergoes the aldol-Tishchenko reaction in typically high yields and with complete 1,3-anti diastereocontrol. Evaluation of a broad range of metal alkoxides as catalysts and optimization of the reaction protocol led to a modified zirconium alkoxide catalyst with attenuated Lewis acidity and dichloromethane as solvent, which resulted in suppression of the undesired acyl migration to a large extent. Various ketone aldols have been prepared and subjected to the general process, giving rise to a broad range of differently substituted 1,3-anti-diol monoesters, which may be hydrolyzed to the corresponding 1,3-anti-diols.

In search of open-chain 1,3-stereocontrol

Methylation of methyl 4-phenylpentanoate 25 gives the diastereoisomers methyl (2RS,4SR)-2-methyl-4-phenylpentanoate 26 and methyl (2RS,4RS)- 2-methyl-4-phenylpentanoate 27 in a ratio of 44:56. The aldehydes 3-dimethyl(phenyl)silylbutanal 28, 3-dimethyl(ph

Stereocontrolled reductive amination of 3-hydroxy ketones

syn-1,3-Aminoalcohols are synthesized in high diastereomeric excess by reductive amination of 3-hydroxyketones with sodium cyanoborohydride in the presence of benzylamine.

Chiral Organometallic Reagents, I. Stereoselective Exchange of Diastereotopic Bromine Atoms by Lithium in 1,1-Dibromo-3-(trimethylsilyloxy)alkanes

Bromine-lithium exchange in 1,1-dibromo-3-(trimethylsilyloxy)alkanes 4 and 6 affords the carbenoids 8 and 14, which have been added to ketones, aldehydes, arylboronates, and silylating agents.Diastereoselectivity in the generation and trapping of the carb

STUDIES ON THE DIASTEREOSELECTIVE REDUCTION OF β-HYDROXY KETONES TO 1,3-DIOLS WITH COMMON HYDRIDE REAGENTS

Some common reducing agents were employed in the diastereoselective reduction of several β-hydroxy ketones to their corresponding syn-1,3-diols.The use of NaBH4 with a Ti(IV) chelating species produced syn diols with a moderate to good selectivity significantly depending upon the reaction conditions chosen (solvent, temperature, nature of the titanium species).The use of LiAlH4 at low temperature, in the presence of LiI, showed a high selectivity for reduction to syn diols, thus demonstrating a possible chelating role of lithium.Some interesting preliminary results have been also obtained in the diastereoselective reduction of MEM-protected β-alkoxy ketones.

1,3-SYN DIASTEREOSELECTIVE REDUCTION OF β-HYDROXYKETONES WITH DIISOBUTYLALUMINUM HYDRIDE AND TRIBUTYLTIN HYDRIDE

1,3-Syn diastereofacial selectivity (12 : 1) has been achieved in a facile reduction of β-hydroxyketones with DIBAL-H.Tributyltin hydride also has shown 1,3-syn selectivity.